Caribbean Charter | Professional Crewed Yacht Charters

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St. thomas, virgin islands, tel: 340-774-5630.

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LUXURY YACHT CHARTERS & SAILING VACATIONS

All-Inclusive Yacht Charters

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.

Kayak, snorkel, sail, scuba dive, paddle-board, fish, island hop, or simply relax aboard a Caribbean yacht charter. We’ve listed just a few reasons below:

Fully Crewed, Catered & Private Sailing Yacht Charters Tailored for You & Your Guests

  • Private Sailing Vacation
  • Create Your Own Custom Itinerary
  • Visit Untouched Islands
  • Different Caribbean Destinations
  • Unforgettable Memories
  • Fully Prepared Meals by Your Own Private Chef
  • Underwater Adventures with Sea Life

We Look Forward to Welcoming You Aboard!

Explore Destinations like the British Virgin Islands, St. John, Grenadines, Bahamas, and St. Marten!

All-Inclusive Yacht Charters are with a captain and your own personal chef they tailor your charter for a needs and requests. allows you enjoy sailing in beautiful large vessels such as; Catamarans, Monohulls and Power Yachts designed for comfort.  For more information, please visit our: Frequently Asked Questions.

Choose a vessel from our inventory:

Couple enjoying sunbathing on a yacht - Caribbean Charter

FEATURED YACHT CHARTERS

sailboat charter caribbean

  • Sleeps 12 Guests
  • 7 Kings, 1 Twin

sailboat charter caribbean

  • 157′ Mega Yacht
  • 2 Kings, 2 Queens,
  • 2 Doubles, 2 Twins, 2 pullman

Catamaran-Yacht-Charter-Ultra

  • Sleeps 8 Guests
  • 3 Queens, 1 Twin

BLUE HORIZON

Catamaran-Yacht-Charter-Blue-Horizon

  • Sleeps 6 Guests
  • 2 Kings, 1 Queen

POPULAR YACHT DESTINATIONS

the-baths-caribbean-charter

Other Yacht Charter Destinations

  • Florida Key’s
  • St. Thomas, USVI
  • British Virgin Islands

DAY CHARTER BOAT RENTALS

sailboat charter caribbean

Scout in the Virgin Islands

Full-day charters 9:30 – 4:30 PM. US Virgin Islands or the British Virgin Islands $1800. Bar hop or visit exclusive beaches while you stop and snorkel along the way!

Our 38′ Scout comfortably holds 6+ passengers, allowing plenty of room to lay out on the sun deck or relax in the shade while enjoying a drink and listening to your favorite music.

sailboat charter caribbean

1/2 Day or Full Day Charters

  • Captain and Crew
  • Complementary snorkel equipment and fins
  • Coolers stocked with Ice, water and assorted beer.
  • Abundance of cushioned seating and lounging areas in shade or sun.
  • Dry storage for your personal items and gear.
  • Full size restroom
  • All required USCG approved safety equipment, and extra features not required by law.
  • Food, Liquor, Fuel and Crew Gratuity is NOT included.

sailboat charter caribbean

Fishing in the Virgin Islands

Everyday is a great day to book a fishing excursion. We can give you the fishing trip of a lifetime. Whether you are an experienced fisherman or just getting started the  mahi-mahi, tuna, wahoo, and big marlin await.

We have all the latest and best fishing gear, outriggers, navigation and sonar, along with some of the best and most experienced captains in the islands. Whether you choose a half day (3.5 hours) or a full day (7 hours) off shore trip, you’re guaranteed to have a good time.

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Find Your Perfect Yacht

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Caribbean yacht charters - one resource for every luxury charter yacht

The proven resource for crewed yacht charter in the caribbean.

From the moment you contact us, you will be helped by an experienced and knowledgeable specialist who will take the time to understand your unique needs and preferences for your caribbean vacation. They will be your dedicated specialist and our exceptional personal service will answer every question.

The largest choice of crewed Caribbean yachts?

Absolutely, with our relationships built over decades we truly do have access to EVERY crewed private charter yacht based in, or visiting, every part of the Caribbean.

Whatever the type of yacht for your Caribbean charter, your vacation budget, or the size of your party, our specialists will guide you in choosing the ideal yacht for your Caribbean charter. It's your vacation to explore the islands the very best way possible - on a Caribbean charter yacht.

Browse different types of Charter Yachts in the Caribbean

sailboat charter caribbean

Motor Yachts

This category of Caribbean yachts include mega yachts, super yachts, and all sizes of power yachts. With the maximum space for guests, both inside and out, these types of yachts offer excellent vacations. You can choose from a fast, agile yacht, one that is high-end and luxurious, a yacht with a classic design, or one that is contemporary. This is one of the many choices you’ll have when you plan your vacation. See some yachts:-

sailboat charter caribbean

Crewed Catamarans are very popular in the Caribbean , especially in the BVIs. Catamarans offer ample deck space that allows everyone to relax together during their charter, sharing the same views throughout the voyage. Caribbean catamarans can typically accommodate between 6 and 12 guests. See some yachts:-

sailboat charter caribbean

Sailing Yachts

If you are looking for a winter getaway, there is no better place to charter a sailing yacht than the Caribbean! Feel the warm, tropical breeze on your face. Experience the exhilaration as the wind fills the sails and the yacht is suddenly moved along by just the wind. Savor the magnificent beauty of the Caribbean as you sail silently from one island to the next. Although typically offering smaller spaces for guests, sailboats deliver a truly unique caribbean charter vacations . See some yachts:-

Sample Charter Yachts in the Caribbean

sailboat charter caribbean

ODYSSEA. The 59' sailing catamaran Odyssea is ready to take you and your guests on your next adventure. Throughout she offers relaxing areas to lounge and enjoy the voyage, while enjoying the company of others or absorbing the serenity of the sea. Her spacious cockpit area offers large dining table, sun pad across the back, and wet bar. See ODYSSEA:-

sailboat charter caribbean

SOUTH. Get ready for adventure when you step on board the 180' mega yacht South. You and your guests will find plenty to do, as she offers plentiful spaces for lying out to enjoy the sun, enjoying a movie or game in the sky lounge, working out in the Techno gym with an amazing view, or enjoying the on deck Jacuzzi and watersports. See SOUTH:-

sailboat charter caribbean

IMPULSE. The beautifully maintained motor yacht Impulse offers 87 feet of opulence at sea. She features three well-appointed cabins, a main salon, a bow with sunpads, flybridge with Jacuzzi, and a full complement of watersports including water skis, wakeboard, standup paddleboards, fishing gear, and the list goes on. See IMPULSE:-

sailboat charter caribbean

LIQUID SKY. The 67' sailing catamaran Liquid Sky was launched in 2024 by Fountaine Pajot. With four cabins, she accommodates as many as eight guests, and offers a number of places for you to hang out and enjoy the journey, including on the bow soaking in the in deck Jacuzzi, up on the flybridge taking in the views, or on the aft deck with al fresco dining. See LIQUID SKY:-

sailboat charter caribbean

MARIAH PRINCESS III. The 77' Lagoon built sailing cat Mariah Princess III was built in 2020. She offers two queen cabins and two king cabins, all en-suite. The master cabin has a private deck, the flybridge offers an on deck Jacuzzi, and she has a generous complement of watersports, including onboard SCUBA. See MARIAH PRINCESS III:-

sailboat charter caribbean

TRUE STORY. The 67' sailing catamaran True Story is ready to give you and your guests a fun and exciting charter in the beautiful waters of the Caribbean. She offers a spacious main salon, large cockpit with al fresco dining and lounge, and flybridge with conversational area. You and your guests can also enjoy a long list of water toys throughout your journey. See TRUE STORY:-

Charter a yacht in the BVI's

The British Virgin Islands include Tortola, Jost Van Dyke, Virgin Gorda, and more. There’s no better way to experience the waters and beaches of the BVI's than on a private Caribbean charter with a full crew to pamper you. Of all the islands in the Caribbean, the Virgins are furthest north. This makes them very convenient due to the proximity to San Juan and due to their direct flights from the United States. Catamaran sailing vacations and crewed sailing charters are very popular in the islands, and their protected waters make them a favorite spot for guests that are taking their first private Caribbean yacht charter. To learn more about them:

Charter a yacht in the USVI

The U.S. Virgin Islands consist mainly of the three large islands of St. Thomas, St. Croix, and St. John. With lovely bays, long beaches, lush nature preserves, fabulous diving spots, and excellent, onshore evening entertainment, many choose to vacation in the USVI’s. Caribbean charters often visit both the BVI’s and USVI’s during the same week, as they are close to one another and the waters are generally calmer than in other parts of the Caribbean. They in general are also home to the largest fleet of crewed, all-inclusive, luxury catamarans. To find out more about them:

Charter a Caribbean yacht

The Leewards are situated in the middle of the Caribbean Island chain. The major airports are located on St. Maarten and Antigua. Due to the English, Dutch, and French influences everywhere you look, they exhibit the best example of cultural sophistication anywhere within the Caribbean. If you are looking to see where the rich and famous go on vacation, you will want to visit the island of St. Barts; for many this is a must stop for a Caribbean yacht charter. Many mega yachts are available for rental in St. Maarten, as it has become a popular mega yacht Caribbean base for the winter. To learn more about the Leewards:

Grenadines

The Grenadines are also called The Windward Islands. Oftentimes our guests will choose a sailing charter over a motor yacht when in the Grenadines, due to the more constant tropical breezes that occur. The islands are much less developed than the rest of the Caribbean, and the inhabitants live on their own time schedule, which enhances the feeling of getting away. The northern most island accessible by air is ST. Vincent, while the southern tip’s major airport is on Grenada. There are fewer Caribbean charter yachts based here; however, occasionally some charter yachts are happy to relocate in order to offer a vacation that happens a little off the beaten path. To find out more about the Grenadines:

What Type of Charter Yacht?

There are all types of Caribbean yacht charters available, including mega yachts, power yachts, catamarans, and sailboats. We have helped countless clients choose the right charter yacht, learning what features and amenities make a difference on caribbean charter yachts. Learn more about different types of Caribbean yachts.

Where Can You Go?

Typically you’ll choose between the Virgins, Leewards, and the Grenadines to charter your yacht. Beyond the region, it is your Caribbean to explore. It’s important for you to remember that there is no cruise ship itinerary to worry about! Your itinerary will be custom designed specifically for you, with you, and is flexible to changes during your charter. We have put together some samples for you to get an idea of what you might like to do while on vacation in the Caribbean. Interested in seeing a sample cruise itinerary ?

sailboat charter caribbean

Find Your Perfect Yacht for a Caribbean yacht charter

To see the Caribbean yachts we have in our online database, please select a yacht type and your budget below. Please keep in mind that we do not have every available yacht online. There are many more yachts available for you to choose from when you contact one of our specialists.

For your personalized selection including yachts not online:- Email us now

sailboat charter caribbean

Caribbean Charters - When To Go.

One of the lovely things about the Caribbean is that the temperatures remain consistent throughout the year; however, there are some other weather considerations that you will want to factor in when making your caribbean yachting vacation plans. Read More....

Vacations here are most popular between November and July.

If you are thinking of a megayacht, you will want to keep in mind that many of these private yachts which are Caribbean based in winter leave in the late spring and early summer months. They will return again in early winter; however, this does limit their availability. To charter a mega yacht, you will want to make sure that you do so well in advance.

Motor, sail, or catamaran yachts, on the other hand, often have selections available year round. Holidays like Christmas, New Year’s, and Easter do need to be planned for as early as possible as these are very popular charter times.

The availability for Caribbean charters can also be affected by the weather in other climates, for instance, when the severity of the weather is bad in the United States or Europe, especially between January and February, the charters are often booked. This is due to many clients looking for a break from the cold.

What Do Our Clients Say About The Caribbean?

Are you excited yet? You should be! Our clients have enjoyed fantastic Caribbean vacations. There is an endless number of places to visit in the Caribbean, from smaller islands to absolutely must be seen locations like St. Barts. Read some of our Caribbean charter reviews from clients who booked a Caribbean charter with us.

Ready to learn more about Caribbean charters?

We are specialists who will make your trip a reflection of our expertise! We know clients need to be confident in their charter vacation plans, so we encourage our clients to benefit from the knowledge base we’ve been building for years. You’ll speak to an authority on Caribbean charters without any obligation on your end.

Test our expertise with your questions!

Contact a specialist - available 7 days a week.

sailboat charter caribbean

Yacht Name Search

Do you have a particular yacht in mind? We likely have it online and if not, email or call us for details. Search for it online by name here:

These may also be of interest:

  • Why is crewed charter so unique?
  • Why use a charter broker
  • Can one Broker have access to all yachts?
  • Why you should choose us

International Yacht Charter Group Inc. does not guarantee the accuracy of any information or images displayed. Both are subject to change and may not be current. All information contained herein is not contractual. Continue reading for more details: 2003 - 2023 © All Rights Reserved. Privacy Policy Site map

sailboat charter caribbean

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Caribbean

Find Caribbean Crewed Yachts for the Vacation of a Lifetime

The Caribbean is one of the most popular destinations for yacht charters in the world, featuring crystal-blue waters, white-sand beaches, and more than 5,000 islands and cays to explore. With so many islands to choose from, your Caribbean yacht charter itinerary can be tailored to your preferences, giving you the perfect opportunity to island-hop and explore everything the tropical islands have to offer while comfortably kicking back inside luxurious accommodations on the water.

On your private yacht charter , you will be able to explore lively harbors, secluded beaches, tropical rainforests, world-class dive sites, and much more. The possibilities are endless!

Caribbean Yacht Charter Highlights

  • More than 5,000 islands and cays to explore
  • A great winter destination
  • Crystal-clear, sparkling blue waters
  • Long stretches of white-sand beaches
  • Luxury hotels, five-star restaurants, and spas
  • Islands with their own unique cultures and cuisines
  • A large selection of crewed yachts for charter

Showing 1–4 of 92 results

Chakra Profile

282.2ft / 84m

More info

239.6ft / 71m

Sherakhan Yacht

228.6ft / 68m

sycara V main

223.7ft / 67m

Caribbean Yachting Season

The Caribbean high season for yacht charters runs from mid-December to early May, with Christmas and New Year’s the most popular and busiest times of the year. But due to the islands’ locations near the equator, temperatures remain ideal throughout the year, making off-season charters just as enjoyable.

Keep in mind, however, that there is an increased chance for storms and hurricanes during the summer season, mainly from mid-August to mid-November. Most charter yachts leave the area during that time.

Caribbean Crewed Motor Yacht Charters

remember when main

Remember ...

162ft / 48m

More info

Sweet Escape

130ft / 39m

unbridled main

116ft / 34m

Caribbean Catamaran Charters

Yacht Bella Vita Front View

105ft / 31m

Catamaran Serenity Now main image

Serenity Now

Karma catamaran

Caribbean Crewed Sailing Yacht Charters

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Area Guide: Caribbean Charter Destinations

A girl snorkeling in the BVI

Are you ready to explore all that the Caribbean has to offer? There are three main island areas in the Caribbean, all fantastic destinations for Caribbean charter yacht vacations.

The Grenadines

The Grenadines are untouched by mass tourism and industry, and they are the perfect charter destination if you are looking for solitude and you enjoy exploring remote areas. A great combination of lush rain forests and sandy beaches awaits!

This is a great summer charter destination because the islands aren’t usually affected by hurricanes.

The Leeward Islands

Leeward Islands yacht rentals offer the perfect combination of luxury and solitude. You can visit the glitzy islands of St. Maarten and St. Barts one day and get lost in the remoteness and tranquility of Anguilla the next day.

These islands are rich in history and offer great restaurants, upscale resorts, and trendy harbors.

The Virgin Islands

The Virgin Islands are the perfect location for first-time charterers and families because of their calm waters, protected natural anchorages, and short distances between the islands.

The BVI are a great destination for a catamaran or sailing yacht charter. Caribbean locations here have constant yet mild trade winds year round, and the area offers fantastic diving and snorkeling.

Where Can I Charter a Yacht?

When you choose Worldwide Boat as your Caribbean yacht charter broker, we can help you charter a luxury boat anywhere in the Caribbean or anywhere else you’d like to go, from the Mediterranean to Alaska to the Galapagos Islands.

How Do I Book a Private Yacht?

The best Caribbean yacht charters can be booked in just a few easy steps:

  • Choose our experienced yacht charter specialists to assist you through the process of booking a yacht.
  • Search by destination or by boat, or use our advanced search tool to filter your options by the number of guests, yacht type, destination, and/or your budget.
  • Pick the option that best fits your needs and your dream vacation.
  • Reserve your yacht by signing a contract with the yacht owner.
  • Enjoy your vacation!

How Much Does it Cost to Charter a Yacht in the Caribbean?

Weekly rates for Caribbean boat charters are dependent on a number of factors, including the type of yacht, the season, and your destination. Motor yachts, for example, typically range from $15,000 (yachts up to 80 feet) to $150,000 or more (yachts over 150 feet) per week.

During the Caribbean high season (Christmas, New Year’s, and January/February), yacht charter Caribbean prices tend to increase slightly. Areas with large charter fleets, like St. Martin, tend to have more competitive pricing than areas with smaller fleets.

How Much Does it Cost to Charter a Catamaran in the Caribbean?

Most catamarans offer all-inclusive rates, which start at $10,000 for catamarans under 50 feet and run up to $50,000 or more for catamarans of 80 feet or more. The Caribbean is an ideal destination for a catamaran charter, and across the region, you’ll find a variety of sailing and power cats available for charter.

Ultimately, the cost of a catamaran charter is dependent on the time you visit, where you go, local taxes, and the number of ports you visit. A luxury yacht charter in the Caribbean’s high season (New Year’s or Christmas) will cost significantly more than a catamaran charter in summer.

Can I Rent a Yacht for a Day?

Rates for yacht rentals are usually weekly, but when you talk to a Caribbean yacht charter broker at Worldwide Boat, we can look at your budget, plans, and interests to help you get the best experience possible.

Caribbean Yachting Hotspots

Caribbean sailing charters give you access to white-sand beaches and laid-back island vibes, but they can also offer action-packed itineraries. From island-hopping and hiking to snorkeling and cliff-jumping, adventure awaits on a Caribbean yacht charter!

Some of the region’s must-see destinations include:

  • St. Martin : Known for its upscale eateries and amazing cuisine, as well as high-end spas, shopping and casinos, St. Martin is the yachting capital of the Caribbean. This island is part French and part Dutch, and it’s close to islands like St. Barts and Anguilla, making it a favorite jumping-off point for island-hopping adventures.
  • St. Barts : St. Barts (sometimes called St. Barths) beckons A-listers to its posh beach clubs, fashionable shops, and five-star eateries. Visitors will find a collection of truly spectacular powdery beaches, Michelin-starred restaurants, and excellent shoreside amenities, all within cruising distance of St. Martin.
  • Antigua : Antigua epitomizes the relaxation and bliss of the Caribbean. Known for its 365 beaches (one for every day of the year), the tiny island is a sailor’s dream, offering warm waters, steady winds, safe anchorages, and a lively regatta calendar.
  • Grenada : Grenada is revered for its beautiful beaches, abundant marine wildlife, and vibrant cuisine (spiced with local nutmeg, mace, and allspice). Spend a day relaxing on Grand Anse Beach, which is consistently ranked one of the best in the world. Island-hop to neighboring isles like Petite Martinique, or spend a day snorkeling one of Grenada’s famous reefs.
  • Anguilla : Anguilla is one of the most tranquil Leeward islands. Escape to Dream Bay or one of the numerous nearby coral cays for some supreme R&R. A diving and snorkeling mecca, Anguilla is home to some of the Caribbean’s best shipwreck dives. Plus, the island boasts a calendar of must-see festivals and events, including a jazz festival in November and Carnival in August.

Why Charter a Yacht in the Caribbean?

The best Caribbean yacht charters offer a bit of everything: Relaxation, sun-soaked beaches, delicious culinary treats, refreshing rum-infused cocktails, and calm waters for cruising. Here are some highlights:

The Inescapable Beauty of White-Sand Beaches

Caribbean beaches have almost a mythical quality to them. It’s no wonder explorers were once willing to board wooden ships and travel thousands of miles just to see them in person.

Every island offers a selection of untouched and charming beaches for you to explore. From one-of-a-kind places like “Pig Beach” in the Bahamas to the cosmopolitan Great Bay Beach in Philipsburg, St. Martin, the beaches across the Caribbean offer legendary sights and attractions.

Colorful Celebrations and Friendly Faces

The Caribbean is known for its parades, bars, nightclubs, and parties, not to mention world-famous cocktails. When you want to step off of your luxury yacht charter, Caribbean shores and islands offer a world of fun to immerse yourself in.

A few must-see events include the St. Barth’s Bucket (if you’re into superyacht racing), the annual Carnival celebration, and the St. Lucia Jazz & Arts Festival .

Amazing Wildlife and Adventure

If snorkeling in vibrant and colorful coral reefs, diving into underwater museums, or parasailing over clear waters are some of the items on your bucket list, you can certainly get it all done during your visit to the Caribbean.

You’ll find a variety of unique adventures, from the underwater sculpture park of the Grenadines to the natural seaside baths in Virgin Gorda and hiking the Pitons in St. Lucia. The Caribbean gives you to plenty of chances to get outside and enjoy yourself.

Nonstop Relaxation

Because the area is so close to the equator, the Caribbean offers warm weather to lounge in all year round. Feel pampered aboard a luxury crewed rental yacht, and then feel calm while sinking your toes into soft, powdery white sand. Enjoy the spas, rum cocktails, and quiet, isolated beaches: Charter guests can experience supreme relaxation in the Caribbean.

Book Your Caribbean Charter With Worldwide Boat

Discover the beauty of the Caribbean with a luxury crewed yacht charter. Contact a broker with Worldwide Boat today to learn more about available yachts and itineraries for the Caribbean.

Last edited by Katja Kukovic

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Turquoise Yacht

182ft / 54m

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142ft / 42m

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Book an unforgettable crewed yacht charter vacation.

View available yachts:.

Book with the Caribbean specialists. For over 19 years we have been a leading yacht charter brokerage connecting groups like yours with the best crewed yachts available for charter in the Caribbean including the Virgin Islands / BVIs / USVIs, Leewards, Grenadines and Bahamas.

Utilize out firsthand knowledge about available charter yachts, crews and locations to book the best yacht and crew for your budget and travel style.

Start planning your vacation today!

Sail away to white sand beaches, consistent Caribbean trade winds, clear blue water, sheltered island bays great for cruising, world-class dive sites, award winning yachts and crew, and sunshine every day of the year.

crewed catamaran charters

Power Yachts

Specials and last minute discounts:.

These crewed catamaran charter specials are available for new reservations sailing from St Thomas or Tortola in the Virgin Islands, or elsewhere in the Caribbean. Contact us now for further information and a no-obligation quote.

See all of the current crewed yacht charter specials and discounts.

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Catamaran Salty Dog

Stephen M, aboard Catamaran Salty Dog , February 2024  sailing the Virgin Islands

Catamaran Moon Shadow

Max M, aboard Catamaran Moon Shadow , February 2024  sailing the British Virgin Islands

Catamaran Gambit

Mackie M, aboard Catamaran Gambit , January 2024  sailing the British Virgin Islands

> See all of our crewed yacht charter reviews

Caribbean Yacht Charter Vacations

A crewed Caribbean yacht charter offers you the freedom to explore this tropical paradise without limits and at your own pace.

With accommodation, a professional captain, a personal chef, all meals, cocktails, wine, beer, snacks, fuel, equipment, and water toys included, few other vacations offer such an extraordinary experience and value.

Itineraries are completely flexible within your cruising area. Sail the diverse US and British Virgin Islands, the undeveloped and resort islands of the Caribbean Grenadines, or charter a luxury power yacht to cruise St. Martin, St. Barts, and Antigua in the Caribbean Leeward Islands.

Sailing Direction's charter brokers help you book a private crewed yacht in the Caribbean for any group size and budget. Whether you're looking for a family sailing vacation, a couple's adventure holiday, a BVI yacht charter, or a honeymoon or anniversary celebration - we've got you covered for an unforgettable crewed yacht charter experience.

sailboat charter caribbean

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797  Crewed Luxury Yachts for Charter in the Caribbean

  • Caribbean Yacht Charter

A Caribbean yachting vacation incorporates vast expanses of crystalline waters and endless clusters of idyllic paradisical islands, making for a picture-perfect family getaway. With its beautiful climate and spectacular coastlines that comprise iconic superyacht hotspots like the  Virgin Islands ,  St Barts  and  Antigua , a yacht rental in the Caribbean has an alluringly evergreen appeal.

Caribbean Yacht Booking Guide:

Caribbean Yacht Charters: At a Glance

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The Caribbean Sea comprises more than 7,000 islands, islets, reefs and cays, and is divided into three island arcs: that of the Greater Antilles in the north, the Lesser Antilles in the south, and the Leeward Antilles to the east.

Tropical islands of the Caribbean

  • Ideal winter destination Boasting all-year-round pleasant weather, its powdery sand beaches and alluringly clear waters make it an especially popular choice for winter yacht charters.
  • Easy-to-reach The Caribbean is well-connected to the US, with a high number of international airports flying directly into the region.
  • Secluded anchorages With more than 7,000 islands and only a small percentage being inhabited, the world is your oyster when it comes to finding serenely beautiful anchorages.
  • Snorkeling and diving paradise The Caribbean is home to some of the world's most impressive snorkeling and diving sites, meaning plenty of exciting underwater adventures where your eyes will be wide with wonder.
  • Excellent superyacht marinas The Caribbean has numerous well-provisioned superyacht marinas to take your pick from, many of which have fantastic dining and shopping opportunities.

7 of the best beaches in the Virgin Islands

While the Bahamas is technically part of the Caribbean region, it is an island nation in its own right, forming part of the Lucayan Archipelago in the Atlantic. That said, the Caribbean is a vast area occupied by thousands of islands, coral reefs and islets, of which the Bahamas forms a part, along with strong political and cultural ties that have created a natural bond with its Caribbean neighbour. 

Practically speaking, however, if you are interested in cruising  the Bahamas  in conjunction with your Caribbean yacht charter, it is highly unlikely you'll be able to manage the distance during a typical 7-day charter, especially for itineraries that incorporate East Caribbean destinations such as Antigua and Saint Martin. You will need to decide which destination you prefer to spend your time in, or extend your charter vacation to incorporate both. 

To find out more about chartering in the region, check out our in-depth Bahamas destination guide for more information.

Tropical beach in the Pitons, St Lucia in the Caribbean

The most popular destinations for renting a yacht in the Caribbean are those located in the Lesser Antilles region, primarily the island groups of the Leeward Islands.  and the  Windward Islands .

For Leeward Island yacht rentals , Antigua, the Virgin Islands, St Martin, St Barts and St Kitts and Nevis garner the most attention, thanks to not only their splendid tropical landscapes but also their extremely well-provisioned superyacht marinas, fine dining options, impossibly hip bars and medley of designer boutiques bound to keep guests entertained from dawn till dusk.

Scattered like pearls along the aquamarine seas, you'll find sun-drenched Martinique, gorgeous Grenada and the ultra-secluded St Vincent and the Grenadines  are the top picks for slow-paced  Windward Island yacht charters .

Although not as popular, the islands that form the Greater Antilles , such as Jamaica, Cuba and Puerto Rico , are just as beautiful and offer an array of spectacular destinations to explore and discover on a luxury yacht charter.

10 top spas to enjoy on a Caribbean yacht charter

Looking for the best superyacht hotspots in the Caribbean? These are the spellbinding locations guests find most enticing. If you are interested in any of these cruising grounds, we strongly advise booking as far in advance as possible.

  • Antigua: the jet-set adore its unbelievable scenery, intriguing historical landmarks, lavish shopping options and a cluster of ivory-white sands coupled with gin-clear waters.
  • St Martin/Sint Maarten : French and Dutch sides of the island combine to bring a fascinating fusion of influences, replete with outstanding diving spots and awe-inspiring topography. 
  • St Lucia : considered the tropical jewel of the Windward Islands, it's virtually unspoiled. Bordered by lush rainforest and dark volcanic sands, it makes for a truly unique anchorage spot. 
  • Grenada : known as the Isle of Spice thanks to being one of the world's largest exporters of mace and nutmeg, its capital St George is regularly called the Caribbean's most picture-perfect town. 
  • St Barts : Well-known for its moniker "St Moritz of the Caribbean" due to its unique Swedish-French colonial heritage, this iconic tiny island is synonymous with glamour, movie stars and designer shopping. 
  • St Croix, US Virgin Islands : The largest of the USVIs boasts a National Park, breath-taking scenic beauty and some of the best dive spots in the Caribbean.
  • Puerto Rico : Affectionately known locally as the ‘island of enchantment’, Puerto Rico is a profusion of vibrant Latin culture entwined with the laid back rhythm of the Caribbean, with pristine beaches, excellent diving spots and exquisite local dishes.

How to spend 24 hours in St Barts on a Caribbean yacht charter

A yacht rental vacation in the Caribbean delights guests with its truly endless number of things to see and do. Here are our top picks:

Don't Miss:

  • Eden Rock St. Barts : one of the most in-demand hotels in the Caribbean, with a seven-star bar and spa.
  • Hermitage Bay, Antigua : kick back and relax on this tropical beach that delivers on sensational views.
  • Bagatelle, St. Barts : overlooking the glittering Gustavia harbor, this sophisticated bar and restaurant is a hugely popular superyacht spot, showcasing the finest of French-Caribbean cuisine.
  • Basil's Bar, Mustique : legendary bar and restaurant designed by Philippe Starck, frequented by royals, supermodels and rockstars for decades.
  • The Cotton House, Mustique : a wellness center unsurpassed in beauty.
  • Watermelon Cay, St John, US Virgin Island s: dreamy islet surrounded by coral reefs and a veritable snorkeling wonderland
  • Rhone Marine Park, British Virgin Islands : the wreck of the RMS Rhone is the BVIs' most popular dive site, and arguably one of the best in the Caribbean.
  • Trunk Bay, St John, US Virgin Islands : all dazzling white sand lapped by the bluer-than-blue ocean, this island paradise ranks consistently among the world’s top 10 beaches.
  • Jardines del Rey archipelago, Cuba : known locally as the ‘King’s Gardens’, this collection of islands is a registered UNESCO Biosphere Reserve and an island-hopper's paradise, offering myriad secluded beaches and sensational sunsets.

A family stroll down a wooden pontoon over a turquoise sea with a sailing yacht in the distance

For anyone looking to get a dose of serious sunshine during the Northern Hemisphere winter, a yacht charter in the Caribbean is a seriously enticing prospect, with St Barts being the clear favorite for Christmas and New Year's Eve, thanks to the showstopping celebrations that take place in Gustavia Harbour.

For avid island hoppers, the Windward islands offer an enchanting itinerary full of sun-kissed isles and laid back charm juxtaposed with chic resorts and heavenly French-based cuisine, not to mention unrivalled vistas and sultry sunsets accompanied by warm rum-laced winds. 

Across all Caribbean destinations, keen divers and snorkelers will be in for a subaquatic treat, and you'll find a wide range of designer boutiques and ultra-high-end resorts peppered across the isles wherever you go.

A dancer wearing a lavish costume of peacock feathers

The Caribbean is a mesmerizing melting pot of cultures and influences, rooted in its rich heritage and undeniably shaped by its history of colonization and waves of immigration. Each island group is highly diverse in terms of its language, music, customs, architecture and cuisine, but it's mainly English, Dutch, French or Spanish colonial influences that are keenly felt. While the mix of languages spoken will differ between island groups, English is widely spoken.

Caribbean cuisine sees influences from Africa, Europe, Latin America and Spain, Meat, seafood, coconut, potatoes, beans and tomatoes tend to feature heavily in local dishes.

Locals are friendly and regularly celebrate their culture, with music, food and wildly colorful festivals held throughout the year.

A luxury yacht rental vacation in the Caribbean is, without doubt, the most sublime way to experience this region, giving you exclusive access to heavenly anchorages that are otherwise impossible to reach or are far from the typical tourist trail.

Guests have boundless fleet options when it comes to a crewed Caribbean charter. If you don't know whether to go for a motor yacht, sailing yacht or catamaran to cruise Caribbean waters, we've laid out the main points worth considering.

Motor Yacht Charters in the Caribbean

Large Super Yachts moored in a marina in the Caribbean

A  luxury motor yacht charter  in the Caribbean is a seven-star way of uncovering the epic beauty of the Caribbean in total privacy. 

For regions with minimal water depth the ideal choice is a motor yacht with low draft, perfect for accessing shallow lagoons and secluded bays.

For those who have their heart set on a superyacht without a shallow draft, dropping anchor further out into deeper waters and then getting a tender ride ashore, so you can get up close and personal to exquisite island reefs and blue lagoons, is the preferred option.

Sailing Yacht Charters in the Caribbean

Yachts in Antigua, Caribbean

Chartering a sailing yacht in the Caribbean is ideal for guests looking for a slower pace to fully lap up the Caribbean rays with more outdoor deck space, and add a little old-school charm to their cruising adventure.

Even better, the majority of sailing charter yachts come equipped with a retractable keel, meaning reaching turquoise shallows is a breeze. But, if you are keen to charter a larger sailing yacht, keep in mind that some may still find their draft too deep for some areas, even with the keel up. 

Catamaran Charters in the Caribbean

Catamarans in the Caribbean

Luxury catamaran charters are a firm guest favourite for those embarking on Caribbean vacation, especially in the Bahamas and the Virgin Islands. Thanks to their shallow draft, catamarans give you the ability to get close to cays and islets guests can savor the thrilling feeling of being able to jump off-board at almost any point. 

The charter cost of a motor yacht, sailing yacht or luxury catamaran rental in the Caribbean will vary according to the vessel's size, age, type, number of crew, as well as the location and duration of the vacation as well as the season it takes place. 

With so many options available, there’s something to suit every type of budget. For convenience we have listed the average prices for motor yacht and sailing yacht charters in the Caribbean below;

  • For motor yacht rentals in the Caribbean, prices can range from $39,167 to $1.4m per week, plus expenses
  • For luxury sailing yacht rentals in the Caribbean, prices can go from $29,855 to $276,495 weekly, plus expenses

Caribbean beach at sunset

The best time for luxury yacht charters in the Caribbean is between November and March, when guests can expect clement weather and vividly blue cloudless skies.

Another aspect to keep in mind is that this is also the time when you will have the largest selection of yachts to choose from, as most charter yachts descend on the Caribbean around November after the Mediterranean season has ended and any yacht maintenance has been carried out, before returning back to the Mediterranean in March/April.

Port de Gustavia in St Barts, Caribbean

The most popular starting point for a Caribbean yacht rental is usually in either Saint Martin/Sint Maarten or  Antigua,  both of which have international airports.

It is certainly possible to begin your charter in other Caribbean destinations, providing this has been agreed with the Owner and charter broker .

Where to End a Caribbean Yacht Charter

For most private Caribbean yacht charters, there isn't one definitive place where to disembark given the vastness of the region. However, what is likely is that you will finish your yacht rental vacation in the same location that you started. For example, the majority of  British Virgin Island yacht charters will begin and end in St Thomas, while for Antigua yacht charters , it'll be the iconic English Harbour.

sample itineraries

Yachts moored in a marina in the Caribbean

The Caribbean offers some of the most spellbinding berthing spots in the world. These tropical, barefoot hotspots are of the finest calibre, surrounded by jaw-dropping scenery, and often feature award-winning restaurants, hip boutiques, beach bars and more.

But which marinas are the best? Below are some charter favorites:

  • Falmouth Harbour, Antigua: impressive marina facilities and scenery, catering to yachts up to 100m.
  • Marina Fort Louis, Saint Martin: offers 150 berths for yachts up to 79m.
  • Crown Bay in St Thomas (USVI): full-serviced marina with 99 slips, including 16 berths for superyachts up to 60m
  • Port Louis Marina, Grenada: idyllically located, with 227 moorings for yachts up to 91m.
  • Port de Gustavia, Saint Barts: widely regarded as one of the most beautiful natural harbours in the world, accommodating up to 152 yachts up to 152m.
  • Puerto Del Rey, Puerto Rico : conveniently located as a jumping off point for yacht charters incorporating the Virgin Islands and Lesser Antilles, this marina has plentiful wet slips, including capacity for yachts up to 200ft (60m) LOA.

Falmouth Harbour in the Caribbean

We strongly advise booking through a qualified  yacht charter broker at least three months in advance for all Caribbean yacht charters. By doing so, you will increase the likelihood of securing your preferred dates and you will have a greater selection of yachts on offer to choose from.

This also ensures your yacht broker has enough time to craft a carefully curated itinerary and secure an overnight berth in the most popular Caribbean marinas.

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Explore the Caribbean

Bahamas Guide

Guide to Bahamas

Virgin Islands Guide

Guide to Virgin Islands

Leeward Islands Guide

Guide to Leeward Islands

Windward Islands Guide

Guide to Windward Islands

Greater Antilles Guide

Guide to Greater Antilles

Turks & Caicos Islands Guide

Guide to Turks & Caicos Islands

Barbados Guide

Guide to Barbados

Trinidad & Tobago Guide

Guide to Trinidad & Tobago

The caribbean yacht charter itineraries.

Make every moment count during your superyacht vacation with our carefully curated yacht charter itineraries, tailored so you can experience the very best of the paradisiacal islands of the Caribbean and ensure your yacht charter is a truly memorable one. Designed by yachting experts, we've cultivated itineraries that will satisfy a range of requirements.

For yacht charter guests seeking a little glitz and glamour on their vacation, a 7-day charter around the Leeward Islands is a must, comprising Caribbean gems such as Saint Barthelemy, renowned for its A-list celebrity culture and designer shopping, as well as the perennial favourite Antigua. For sheer unadulterated bliss, incorporate the Virgin Islands on a 14-day yacht charter, promising idyllic stretches of pristine sands lapped by waters in every shade of blue.

Discovering The Leeward Islands

Discover the Caribbean

Winter Getaways, Tropical Paradise Islands, Snorkeling & Scuba Diving, Crystal Clear Waters, Beautiful Secluded Anchorages, Well-Provisioned Superyacht Marinas

When to Go:

December - March

International Airports:

  • Princess Juliana Airport (St. Maarten)
  • V.C. Bird Airport (St. John's, Antigua)
  • Luis Muñoz Marín Airport (Carolina, Puerto Rico)
  • Grantley Adams Airport (Bridgetown, Barbados)
  • Lynden Pindling Airport (Nassau, The Bahamas)

Luxury Yachts for Charter in the Caribbean 2024 & 2025

Crewed charter yachts in the caribbean.

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Queen Miri Yacht Charter in Caribbean

92m   Neorion

from $1,094,000 p/week ♦︎

Whisper Yacht Charter in Caribbean

115m Lurssen

115m   2021

from $2,874,000 p/w eek ♦︎

Black Pearl Yacht Charter in Caribbean

Black Pearl 14

105m Oceanco

105m   2018

Christina O Yacht Charter in Caribbean

Christina O 34

99m Canadian Vickers

99m   1943/2020

from $774,000 p/w eek ♦︎

Carinthia VII Yacht Charter in Caribbean

Carinthia VII 12

97m Lurssen

97m   2002/2023

from $1,547,000 p/w eek ♦︎

Faith Yacht Charter in Caribbean

97m Feadship

97m   2017/2022

from $1,775,000 p/w eek ♦︎

CC-Summer Yacht Charter in Caribbean

CC-Summer 12

95m Lurssen

from $1,769,000 p/w eek ♦︎

Whisper Yacht Charter in Caribbean

from $1,327,000 p/w eek ♦︎

Lady S Yacht Charter in Caribbean

93m Feadship

from $1,556,000 p/w eek ♦︎

Aquarius Yacht Charter in Caribbean

Aquarius 12

92m Feadship

from $1,500,000 p/w eek

Queen Miri Yacht Charter in Caribbean

Queen Miri 36

92m Neorion

92m   2004/2023

from $1,094,000 p/w eek ♦︎

Lady Lara Yacht Charter in Caribbean

Lady Lara 12

91m Lurssen

91m   2015/2023

from $1,400,000 p/w eek

Nero Yacht Charter in Caribbean

90m Corsair Yachts

90m   2007/2021

from $497,000 p/w eek

Dar Yacht Charter in Caribbean

90m Oceanco

90m   2018/2024

from $1,334,000 p/w eek ♦︎

Barbara Yacht Charter in Caribbean

89m Oceanco

from $1,100,000 p/w eek

Samsara Yacht Charter in Caribbean

89m   2015/2023

Maltese Falcon Yacht Charter in Caribbean

Maltese Falcon 12

88m Perini Navi

88m   2006/2023

from $490,000 p/w eek

Chakra Yacht Charter in Caribbean

86m Scheepswerf Gebr. van der Werf

86m   1998/2024

from $531,000 p/w eek ♦︎

Man of Steel Yacht Charter in Caribbean

Man of Steel 12

86m Oceanco

86m   2010/2023

from $1,000,000 p/w eek

HBC Yacht Charter in Caribbean

86m Abeking & Rasmussen

86m   2009/2024

from $939,000 p/w eek ♦︎

O'Ptasia Yacht Charter in Caribbean

O'Ptasia 12

85m Golden Yachts

85m   2018/2024

from $1,001,000 p/w eek ♦︎

Victorious Yacht Charter in Caribbean

Victorious 12

85m Ak Yachts

from $890,000 p/w eek ♦︎

Le Ponant Yacht Charter in Caribbean

Le Ponant 32

84m   1990/2022

from $506,000 p/w eek ♦︎

Savannah Yacht Charter in Caribbean

Savannah 12

84m Feadship

84m   2015/2020

from $1,111,000 p/w eek ♦︎

Alfa Nero Yacht Charter in Caribbean

Alfa Nero 12

81m Oceanco

81m   2007/2024

from $812,500 p/w eek *

Elements Yacht Charter in Caribbean

Elements 12

80m Yachtley

from $889,000 p/w eek ♦︎

Excellence Yacht Charter in Caribbean

Excellence 12

80m Abeking & Rasmussen

from $1,150,000 p/w eek

Amaryllis Yacht Charter in Caribbean

Amaryllis 12

78m Abeking & Rasmussen

78m   2011/2022

from $770,000 p/w eek

Malia Yacht Charter in Caribbean

78m Golden Yachts

78m   2023/2024

from $811,000 p/w eek ♦︎

Yersin Yacht Charter in Caribbean

from $480,000 p/w eek

Huntress Yacht Charter in Caribbean

Huntress 12

76m Lurssen

76m   2009/2022

from $725,000 p/w eek

Kensho Yacht Charter in Caribbean

75m Admiral Yachts

from $998,000 p/w eek ♦︎

Arrow Yacht Charter in Caribbean

75m Feadship

from $900,000 p/w eek *

M'Brace Yacht Charter in Caribbean

75m Abeking & Rasmussen

from $880,000 p/w eek

Starburst IV Yacht Charter in Caribbean

Starburst IV 12

from $1,010,000 p/w eek ♦︎

Siren Yacht Charter in Caribbean

74m Nobiskrug

74m   2008/2013

from $561,000 p/w eek ♦︎

Laurel Yacht Charter in Caribbean

73m Delta Marine

73m   2006/2015

from $525,000 p/w eek

Nautilus Yacht Charter in Caribbean

Nautilus 12

73m Picchiotti

from $834,000 p/w eek ♦︎

Titania Yacht Charter in Caribbean

73m Lurssen

73m   2006/2020

from $615,000 p/w eek

Quantum of Solace Yacht Charter in Caribbean

Quantum of Solace 12

73m Turquoise Yachts

73m   2012/2022

from $574,000 p/w eek

Game Changer Yacht Charter in Caribbean

Game Changer 17

72m Damen Yachting

72m   2017/2020

from $450,000 p/w eek

Arbema Yacht Charter in Caribbean

72m   2010/2023

from $600,000 p/w eek

Axioma Yacht Charter in Caribbean

72m Dunya Yachts

72m   2013/2020

from $660,000 p/w eek

Talisman C Yacht Charter in Caribbean

Talisman C 12

71m Turquoise Yachts

71m   2011/2020

from $567,000 p/w eek

Joy Yacht Charter in Caribbean

70m Feadship

from $650,000 p/w eek

Sherakhan Yacht Charter in Caribbean

Sherakhan 26

70m Vuijk Scheepswerven

70m   2005/2022

from $594,000 p/w eek ♦︎

Vassa Yacht Charter in Caribbean

69m Feadship

69m   2012/2019

from $610,000 p/w eek ♦︎

Sycara V Yacht Charter in Caribbean

Sycara V 12

68m Nobiskrug

68m   2010/2024

Wayfinder Yacht Charter in Caribbean

Wayfinder 12

68m Astilleros Armon

from $375,000 p/w eek

Loon Yacht Charter in Caribbean

67m Icon Yachts

67m   2010/2020

from $540,000 p/w eek

Vertigo Yacht Charter in Caribbean

67m Alloy Yachts

67m   2011/2019

from $361,000 p/w eek ♦︎

Calex Yacht Charter in Caribbean

67m Benetti

from $680,000 p/w eek

Global Yacht Charter in Caribbean

67m Shadow Marine

67m   2007/2008

from $120,000 p/w eek

Okto Yacht Charter in Caribbean

66m   2014/2023

Alchemy Yacht Charter in Caribbean

66m Rossinavi

from $637,000 p/w eek *

Invictus Yacht Charter in Caribbean

Invictus 12

66m Delta Marine

66m   2013/2020

from $650,000 p/w eek *

Triumph Yacht Charter in Caribbean

65m Benetti

Ventum Maris Yacht Charter in Caribbean

Ventum Maris 12

66m   2011/2021

from $530,000 p/w eek

Eternity Yacht Charter in Caribbean

Eternity 17 7 12

65m Codecasa

65m   2010/2022

from $390,000 p/w eek

Illusion Yacht Charter in Caribbean

Illusion 12

65m   2013/2019

from $462,000 p/w eek

Resilience Yacht Charter in Caribbean

Resilience 12

Seanna Yacht Charter in Caribbean

65m   2011/2021

Silver Angel Yacht Charter in Caribbean

Silver Angel 12

64m Benetti

64m   2009/2015

from $425,000 p/w eek

Moca Yacht Charter in Caribbean

64m   2016/2021

from $475,000 p/w eek

SuRi Yacht Charter in Caribbean

63m Halter Marine

63m   1978/2022

from $350,000 p/w eek

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Crewed Luxury Yachts in the Caribbean

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Top 'Things To Do' in the Caribbean

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Caribbean Yacht Charter Q&A

The best time to visit the Caribbean is generally December to April, when it's a little cooler and less humid. But the best month to visit can differ depending on the island, budget and interests you have. For example, some yacht charter guests may decide to visit May to June and late November, when weather is still fantastic but there are fewer crowds.

We advise booking your Caribbean yacht rental at least three months in advance to ensure you get the yacht you desire. The longer you leave it, the fewer choices you will have to rent in the Caribbean.

For your Caribbean superyacht charter, you will need to provide a completed charter agreement and 50% of the charter fee as a deposit. This is payable once the contract has been signed.

When booking a Caribbean yacht rental, do keep in mind the costs that aren't included in the base rate, namely VAT and the APA (Advance Provisioning Allowance). The APA is usually paid in advance of the charter and is commonly set at 30% of the charter fee. This allowance covers expenses such as fuel, berthing, food and drinks, as well as any special requests. 

Please consult your yacht charter broker for any other costs you may need to factor in for your yacht charter in the Caribbean.

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What does 'All Inclusive' mean?

All inclusive rates typically include: all your breakfasts, lunches, dinners, snacks and Standard Ship's Bar, which includes your alcoholic and non alcoholic beverages. Excluded are airport transfers costs, onshore excursions and tours, as well as any food or beverages purchased ashore. Although optional, crew gratuity is customary at 15% - 20% of the charter rate for the Caribbean and 10% - 15% for the Mediterranean. *Inclusions and exclusions vary by yacht, as each offers unique terms. Please contact us for a custom proposal that details the yacht’s availability, pricing, as well as the list of the inclusions and exclusions for that particular yacht.

What does 'Plus Expenses' mean?

Included are the Yacht and its onboard equipment as well as the Captain, Chef and Crew’s services.Excluded are food and beverages, fuel for the yacht and its tender, any dockage, airport transfers costs, onshore excursions and tours, as well as any cruising permits, licenses and other charter related expenses. Crew gratuity, although optional is customary at 15% - 20% of the charter rate for the Caribbean and 10% - 15% for the Mediterranean. *Inclusions and exclusions vary by yacht, as each offers unique terms. Please contact us for a custom proposal that details the yacht’s availability, pricing, as well as the list of the inclusions and exclusions for that particular yacht.

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The Best Crewed Yachts ‍ For Your Perfect Vacation.

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Plan Your Next Adventure

Book an unforgettable yacht charter vacation.

Sail Play Dine Yacht Charters is here to help you plan a trip you’ll never forget. Experience the vacation of a lifetime aboard a luxury, all-inclusive, professionally crewed charter yacht in the US and British Virgin Islands, Bahamas, and beyond! We take care of your every need to match you with the right boat and crew at the best rate guaranteed. We offer a large range of boats that suit every budget and our trusted service comes at no extra cost to you!

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Tell us about your perfect vacation. Destination, preferences, budget, who will be joining you, and what you would like to see and do.

Our team will be in touch with an initial proposal that we’ll refine together. The yacht charter vacation proposal will include our top recommendations tailor-made to match your interests.

Once you decide on your preferred yacht, we can put a complementary hold to secure your dates while you finalize your travel plans. Complete your reservation by paying a deposit fee.

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Plus Expenses Charters generally don't include food and beverages as well as fuel for the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.

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All Inclusive Charters typically include food and beverages you consume in the yacht. Inclusions and exclusions vary by yacht, please contact us for a custom proposal.

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This was one of the very best trips we’ve ever taken and by far the best vacation we’ve taken in the Caribbean.  We have been to many islands and resorts over the last 30 years; all wonderful experiences, but pale in comparison to this vacation.

Beatriz was great in assisting us to choose the right catamaran for 8 of us including two kids on relative short notice and very helpful In answering all kinds of question about the boat, the crew , contract and the possible route.Definitely recommend you use their expertise in choosing your boat and crew  as I will also do the next time I do a charter in the islands .

Jorge Canellas

Fabiola took all the time I needed to choose the perfect yacht vacation for my friends and I for my special birthday.  In the end, all of my needs were met and we had the vacation of a lifetime.  She was extremely patient in explaining all the ins and outs and what to look for as I was choosing the perfect yacht and I so appreciate that.  She also made all the paperwork and pre-vacation planning a breeze.  Thank you Sail Play Dine Yacht Charters!

Esther Kuznetz

Beatriz & Sail Play Dine was wonderful to work with. Top notch service and answered my endless questions regarding this type of vacation that was completely new to me. I highly recommend them!

Karen Skayhan

Half view of below the yacht and half from above the yacht

Why Choose Sail Play Dine?

Our trusted service comes at no extra cost to you! Our commission is paid by the yacht owner and there is no additional cost to you.

Our recommendations are personalized and hand selected. We look forward to working with you to make the right choice.

We are with you every step of the way. Before, during and after your vacation, to make sure it is unforgettable. We are available 24/7 by phone, text, whatsapp, social media or email. Or you could send us a message in a bottle, and we’d respond to that.

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Frequently Asked Questions

Absolutely! In fact, we recommend it. This type of vacation is typically booked 12-18 months in advance, especially when booking during school vacation (Spring Break) and holidays (Christmas and NYE).

Yes, you can! While most charter yacht pricing is based on a weeklong charter, some yachts offer daily rates, allowing you to customize the duration of your trip. However, please note that some yachts may apply a surcharge for charters shorter than 6 nights. The flexibility of charter durations varies by yacht. We’ll discuss your specific needs and give you recommendations.

The Caribbean is a great destination year-round. Temperatures range from around 79°F in December to March to around 84°F from May to October. Winds are slightly higher in winter, and rates may be higher during holiday weeks, particularly from Thanksgiving through Easter. Christmas and New Year's charters are often booked well in advance.

It's unlikely. The rates on Sail Play Dine are provided directly by the charter yacht management. We are promptly informed of any discounts or special offers. Our team at Sail Play Dine maintains strong relationships with all yacht agents. If you're looking for a better rate, contact us, and we'll work with the agents on your behalf to explore available options.

Crewed yacht charters range from $20,000 to $100,000 per week, depending on the yacht's size, age, and capacity. Fees may be all-inclusive or include additional running expenses and APA (Advanced Provisioning Allowance) for luxury motor yachts.

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Color and Contrast: the Complete Sailboat Vacation

Simply the perfect place to take a bareboat or skippered sailing holiday. Such a diverse collection of islands dotting the clear blue sea, each with its own unique appeal. Local cultures that fascinate and entertain, offering a welcome that keeps charterers returning to these waters year after year. With its 7,000 Islands and 28 Island nations, reliable trade winds and long sailing season, the Caribbean is a region that offers an endless amount of holiday enjoyment.

At Sail Connections, we work with all the best charter operators in the Caribbean, sorting through all the available boats and presenting all the best options to suit your vacation plans. Some of our operators offer extra services that are unique to their destinations. We personalize your proposal and give you the benefit of our knowledge and local contacts, to deliver a fabulous sailing holiday wherever there's a boat to charter in the Caribbean. 

Charter Sailing in the Caribbean

The Caribbean's numerous islands give you so many fabulous places to explore, so many diverse cultures to experience, that the permutations for planning a sailing charter are simply too numerous to list. The sailing distances between territories can be very short, and there are countless yacht charter bases scattered across the region. That opens the door to all manner of opportunities – from a seven-day sail around one distinct island nation to a multi-week one-way charter that takes in a wide variety of cultures and geographical features.

The Caribbean yacht charter season is busy from November through July. The peak season is mid-December to March, when winter escapees from North America and Europe arrive in their greatest numbers.

The hurricane season arrives late July and can last until early October, although storms here are rare and tend to deflect northwards towards the USA rather than hit the Caribbean. These months have their advantages in that they are the least costly for chartering, particularly in the British Virgin Islands. At that time of year it is in fact more likely to encounter light winds than it is storms.

As with many yacht charter locations, the shoulder season can be the best time to charter a yacht. In the Carribean that's from April to July. There are less shore-based visitors then, yet you can expect settled and sunny weather with warm, steady breezes prevailing.

We have access to over 30 charter bases in the region, from where you can take a sailboat vacation like no other. We select from the best boats available and guide you into the ideal sailing adventure that matches your interests and level of experience. The sailing options here are just about endless. Hopefully these pages will help you on your way to your much-anticipated Caribbean sailing holiday.

Regional Map of the Main Charter Sailing Areas

A one-way cruise: martinique to grenada, there are quite simply countless itinerary options for sailing the caribbean. for many charterers a downwind cruise offers the crew conditions for maximum enjoyment. so here's a sample north to south course plan that gives you the prevailing breeze abaft. .

Martinique waterfront

Waterfront at Fort de France, Martinique's largest town

Sailing from Martinique to Grenanda you can expect winds primarily from the northeast, especially around peak season either side of Christmas. Sailing this course involves short stretches of open water, with a stiff and steady breeze on your aft quarter. That makes for quick passages with most enjoyable sailing to a choice of Islands, whether it be for a lunch stop and a snorkel, or an overnight stay.

The eastern Caribbean islands that form a distinctive arc on the map are collectively the Lesser Antilles, a mixture of soverign states and territories governed by various powers. A trip along some of this chain exposes the voyager to a wide variety of cultures and customs in places that all sit in the idyllic picture-postcard surroundings of the movies and travel brochures. 

Starting in Martinique and sailing south, you are exploring the Windward Island group of the Antilles.

Tobago-cays

Wildlife viewing at its finest in the Tobago Cays

Like most of this group, Martinique was orginally colonised by France, and French flair is still in evidence there today. Martinique offers excellent on-shore facilities for the visitor, and is a popular base for boat charters. The island is mountainous, but with plenty of white sandy beaches to enjoy, especially in the south.

The next island is St Lucia. It's some 30 nautical miles to Rodney Bay on St Lucia's northwest, so to get there requires an early start. There are several top spots to visit down the island's sheltered western coast. Take time out to investigate Les Deux Pitons.

Another long but relaxing sail to St Vincent and the Grenadines, so-named because of their joint French and British colonial history. St Vincent has its Blue Lagoon that you'll probably overnight in, while the Grenadines island group, some of which confusingly belong to Grenada, provide numerous anchoring options.

Grenadines

Happy charterers enjoying their time ashore in the Grenadines

The Grenadines stretch all the way to Grenada, your final port of call, making this part of the voyage very convenient for a leisurely sail. Call in at one of the uninhabited Tobago cays for a real taste of desert island living, if only for a few hours.

Once offshore Carriacou you are in Grenadan territory. Grenada, like St Lucia & St Vincent and the Grenadines, is now an independent member of the British Commonwealth, but with historical French influence. This is the 'Island of Spice' where nutmeg and mace production are important to the economy. As is tourism, and there is plenty to entertain you before concluding your vacation and departing these fabulous sailing waters.

Once you have experienced all the pleasures of sailing the Caribbean, chances are you'll be back one day for more.

The Best Caribbean Charter Sailing Destinations

Bahamas

British Virgin Islands

US Virgin Islands

US Virgin Islands

Puerto Rico & Spanish Virgin islands

Puerto Rico & Spanish Virgin islands

Cayman Islands

Cayman Islands

St Martin, St Barts, Anguilla, St Kitts & Nevis

St Martin, St Barts, Anguilla, St Kitts & Nevis

Antigua & Barbuda

Antigua & Barbuda

Guadaloupe

Martinique, St Lucia & The Grenadines

Grenada

Latest Blog Posts

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Sailing charter versus resort stay: comparing the costs

A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

Charter catamarans for modest sailing holiday budgets

Charter catamarans for modest sailing holiday budgets

Here we highlight some smaller catamarans finding favour with our charterers in the Mediterranean and elsewhere. Robert is our expert evaluator when it comes to helping you select the right boat for your sailing charter, and the following is his personal take on recent introductions to the charter boat market.

The popular Bali Catamaran in all its variations

The popular Bali Catamaran in all its variations

The Bali catamaran, designed and built specifically with chartering in mind, has become so popular that it’s been hard to keep up with all the new models, hard to spot which one has just the right size and amenities to perfectly fit your group's sailing holiday charter needs. We can help you there.

The value of after-charter destination and boat reviews

The value of after-charter destination and boat reviews

At Sail Connections we offer a personal service based on long experience in the business and close attention to what's happening in the destinations we offer. We have also sailed a large number of those places, and can often speak from personal experience.  But we can't be everywhere.

Chartering in Turkiye: feedback we just have to share

Chartering in Turkiye: feedback we just have to share

Turkey is one of those charter destinations that doesn't fail to pleasantly surprise. We're always delighted when we receive such good reports as we did recently from a New Zealand client.

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We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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Best Caribbean Sailing Charters for Luxury

Welcome to my guide to Caribbean sailing charters. With years of experience in the Caribbean,...

Table of Contents

Welcome to my guide to Caribbean sailing charters. With years of experience in the Caribbean, I understand what makes a great sailing charter. I will provide all the information you need to decide if a Caribbean sailing charter is right for you. I’ll cover everything you need to know about exploring beautiful islands, enjoying crystal-clear waters, and relaxing on luxurious yachts.

Let’s start your journey toward a memorable sailing vacation.

A sleek KAI Sailboat glides across the sparkling Caribbean Sea, epitomizing the adventure and serenity offered by Caribbean sailing charters

Understanding Caribbean Sailing Charters

Caribbean sailing charters offer a unique way to explore the beautiful islands of the Caribbean. Charterers can escape to enjoy adventure, relaxation, and nature.

  • Motor Yachts : Engines power these yachts, offering speed and luxury. They are ideal for those who want to travel quickly between islands.
  • Power Catamarans : Known for stability and speed, these catamarans are great for families and groups.
  • Sailing Catamarans : These provide a smooth sailing experience and are perfect for those who enjoy traditional sailing.
  • Trimarans : With three hulls, these boats offer superior stability and space.
  • Sailboat : Classic sailboats offer an authentic sailing experience and attract traditional sailors.

Sailing in the Caribbean is great. You can visit many islands, experience the local culture, and admire the crystal waters. The trade winds can be consistent, making the sailing fun.

Moreover, many yachts fit every budget and preference. This provides a unique way to explore the world.

Benefits of Caribbean Sailing Charters

Why choose a private yacht for your caribbean sailing charters here are some benefits:.

  • Privacy : Enjoy your own space without the crowds.
  • Flexibility : Plan your schedule and explore at your own pace.
  • Exclusive Destinations : Access secluded beaches and hidden coves.
  • Luxury : Experience top-notch amenities and services.
  • Local Culture : Immerse yourself in the rich culture of the Caribbean islands.

Essential Considerations for Choosing a Private Yacht Charter in the Caribbean

When selecting a yacht charter, consider the following factors:

  • What type of yacht do you prefer?
  • Budget : Determine how much you’re willing to spend.
  • Destination : Choose the sailing destinations that interest you.
  • Group Size : Consider the number of people in your group.
  • Amenities : Decide what amenities are important to you.

Choosing the Right Yacht: How to Select the Perfect Yacht ?

Selecting the right yacht is crucial for a memorable sailing experience. Here’s how to evaluate your options:

  • Size : Choose a yacht that accommodates your group comfortably.
  • Layout : Consider the yacht’s layout for functionality and comfort.
  • Features : Look for features that match your preferences, such as luxury amenities.
  • Crew Services : Decide if you need a crewed yacht, a skippered charter, or prefer a bareboat charter.

Best Islands to Visit for Caribbean Sailing Charters

Explore the best islands in the caribbean for sailing charters:, the british virgin islands.

The British Virgin Islands are famous for their beautiful beaches, marine life, sailing, and nightlife. The largest island in this volcanic chain, Tortola, offers beautiful beaches, natural preserves, peaceful moorings, and the ruins of old forts and mines. The locals are also incredibly welcoming. In addition to eating seafood, Jost Van Dyke Island offers shopping and surfing opportunities.

While sunseekers head to Virgin Gorda’s serene beaches, snorkelers may explore Anegada’s breathtaking caves and coral reefs. Moreover, sailors use line-of-sight navigation for most of the journey.

St. Lucia :

St. Lucia St. offers the Pitons and beautiful scenery. It provides great opportunities for hiking, snorkeling, and staying at luxury resorts.

On one island, you can enjoy a mix of Dutch and French cultures, beautiful beaches, and gourmet dining options.

Choosing the Best Models for Caribbean Sailing Charters

Savarona sailboat.

The SAVARONA sailboat offers a blend of size, layout, and capabilities perfect for various voyages.

  • Size and Layout : Designers created this 93-foot sailboat to accommodate a comfortable number of guests.
  • Features: Serious sailors will enjoy luxury sailing on Savarona.

Max of 7 selections

sailboat charter caribbean

6 2 28.00 m

ARROW OF AYR Sailboat

ARROW OF AYR offers a spacious design and comfort.

  • Size and Layout : This 80-foot sailboat is perfect for larger groups with ample space.
  • Features : stability and luxury; also ideal for relaxed cruising.

sailboat charter caribbean

ARROW OF AYR

Elvis magic sailboat.

Designers created ELVIS MAGIC for those seeking adventure and comfort.

  • Size and Layout : This 66-foot sailboat offers much space, focusing on comfort.
  • Features : Speed and luxury amenities for a thrilling voyage.

sailboat charter caribbean

ELVIS MAGIC

6 1 66.00 Ft

THE DOVE Sailboat

THE DOVE is perfect for intimate groups seeking a tranquil sailing experience.

  • Size and Layout : This 54-foot sailboat is compact and cozy for small groups.
  • Features : Traditional sailing experience with essential amenities.

sailboat charter caribbean

4 2 54.00 Ft

SUMMERWIND Sailboat

SUMMERWIND offers a blend of speed, comfort, and luxury.

  • Size and Layout : This 50-foot monohull sailing yacht is ideal for various group sizes with a spacious design.
  • Features : Luxury amenities with a focus on speed and stability.

sailboat charter caribbean

4 1 50.00 Ft

Navigating the Caribbean Sailing Charters Booking Process

Booking a Caribbean yacht charter involves several steps to ensure a smooth and enjoyable experience. Here’s a straightforward guide to help you navigate the process:

  • Initial Inquiry : Contact us to express your interest and provide basic trip details.
  • Personal Consultation : Discuss your preferences, budget, and any special requirements.
  • Yacht Selection : Choose from our wide variety of yachts based on your needs and preferences.
  • Contracts and Terms : Review and sign the charter agreement, including terms and conditions.
  • Preparation for Your Journey : Plan your schedule, pack essentials, and finalize travel arrangements.
  • Boarding and Setting Sail : Arrive at the marina, meet the crew, and embark on your Caribbean sailing adventure.

Expert Tips for a Perfect Yacht Charter Experience

Make the most of your Caribbean sailing charters with these expert tips:

  • Packing Essentials : Bring lightweight clothing, sun protection, and any personal items you need.
  • Planning Activities : Plan your activities to make the most of your time on the water.
  • Communicating Preferences : Communicate your preferences and needs with the crew to ensure a tailored experience.

Pitfalls to Dodge When Choosing a Yacht Charter

Avoid these common mistakes when selecting a yacht charter:

  • Overlooking Budget : Ensure the charter fits within your budget, including additional costs.
  • Ignoring Crew Needs : Choose a yacht with the right crew size and expertise for your trip.
  • Neglecting Amenities : Make sure the yacht has the amenities you need for comfort and enjoyment.
  • Not Checking Reviews : Read reviews to gauge the quality of the charter service.

FAQS | Caribbean Sailing Charters

What is the best time of year to charter a yacht in the caribbean.

The Caribbean is a year-round charter destination. Hurricane season is from the beginning of June through to the end of November. September and October can generally see more hurricane activity. Windy conditions can be encountered during winter, with calmer conditions during April – June. However, the weather changes and is unpredictable.

What types of yachts are available for charter in the Caribbean?

You can choose from motor yachts, motor sailers, catamarans, and sailboats.

What level of service can I expect?

Your professional crew is proactive and will handle all your luxury yacht charter details. You can relax and unwind. The chef will plan each meal based on your specific preferences. Your captain will guide you to your preferred destination- the quietest beaches, the secluded anchorages, or the liveliest entertainment spots.

What is a private yacht charter?

A private yacht charter combines the best features of a cruise ship and a luxury resort. Travel to a different destination each day with a high degree of pampering and personal attention. Say goodbye to crowds, waiting in lines, and fixed itineraries. Your private yacht has a dedicated crew, various amenities, water toys to enjoy at will, and a tender to take you ashore whenever you please.

Do I need Travel Protection?

We recommend that you protect your vacation investment against various possible losses over which you have no control by purchasing travel protection. We will provide travel protection quotes based on the households on the charter and each person’s date of birth. It is necessary to send us this information.

Please Note: To be eligible for the waiver of pre-existing medical condition exclusion, the protection plan must be purchased within 15 days (Travel Basic) or 21 days (Travel Select) from when you make your initial trip deposit. However, the plan can be purchased anytime before departure.

The product descriptions are only summaries and may be changed without notice. The full coverage terms and details, including limitations and exclusions, are contained in the insurance policy.

Are pets allowed on board?

It depends on the yacht and owner’s policies. Some yachts may allow pets, while others may not. If you wish to bring a pet, kindly inform us, and we’ll check with the yacht owner to see if it’s possible.

Are children allowed on yacht charters?

Many yacht charters are family-friendly and offer amenities and activities suitable for children of all ages, but it’s always best to check with the charter company beforehand.

Choosing the right Caribbean sailing charters involves understanding the booking process, selecting the best yacht, and avoiding common mistakes. Here are three key takeaways to help guide you:

  • Understand the Process : Know the steps, from initial inquiry to boarding.
  • Select the Right Yacht : Choose a yacht that fits your budget, group size, and desired amenities.
  • Avoid common pitfalls: plan your budget, check reviews, and ensure the yacht meets your needs.

This guide gives you all the info you need to decide on your Caribbean sailing charters. Enjoy your journey and the beautiful Caribbean waters!

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Caribbean Sailing Vacations

Fine white sandy beaches, palm trees swaying in the warm breeze and a shimmering cobalt sea like you’ve never seen before. Experience Caribbean yacht charters and banish those winter blues...

Fine white sandy beaches, palm trees swaying in the warm breeze and a shimmering cobalt sea like you’ve never seen before. Boating trip from the archipelagos of the British Virgin Islands or US Virgin Islands sailing to the diverse cultural differences of the Windward and Leeward Islands, there is something for everyone. Discover some of the world’s best scuba and snorkelling, welcoming smiles and, of course, perfect beaches on a Caribbean sailing vacation.

Wherever you choose to go, you’ll find a Sailo boat rental to make your visit unforgettable. After all, the Caribbean looks great from the beach, but to really enjoy the region in all it’s tropical beauty, take to the seas!

Great sailing conditions

The islands of the Caribbean are well known as a world class nautical playground, with great opportunities for exploring by boat all year round. One of the most popular ways to explore the region is with a private yacht charter, meaning more space on deck to relax and soak up the sun and escape the crowds.

You’ll find Caribbean luxury yacht charters with Sailo to match your style, vacation plans and budget. Choose from luxury motor yachts, beautiful classic sailboats and catamarans, or hop aboard a thrilling speedboat ride for a day on the sea.

Enjoy island hopping and exploring hidden bays, set sail to uninhabited cays and islands, or simply hire a boat for a day trip, a private party boat or fishing charter. From a budget friendly sailing vacation, to an indulgent luxury experience, a Sailo yacht charter will fulfil your Carribean dreams.

Discover the Caribbean your way

The Caribbean islands each have their own character, with a mixture of different colonial influences blending with local traditions. From the French flavors of Guadeloupe and Martinique, to the quirky British traditions of Bermuda, Barbados and the BVI's.

With a week long Caribbean catamaran charter, you have full control and can take your time to get to know the region, arriving in style to a new port every day. Get adventurous and find your dream tropical island, jump into that shining sea and say “Hi” to the locals swimming around the plethora of coral reefs. By night, escape and relax, enjoy a sundowner from the deck of your Sailo yacht charter and toast another perfect day in the Caribbean!

Whether you’re looking for a captained yacht, or a bareboat catamaran or sailboat, browse Sailo for your dream Caribbean yacht charters.

The British Virgin Islands (BVI)

Tropical paradise doesn’t come much more stunning than the British Virgin Islands in the eastern Caribbean Sea. This British overseas territory offers the opportunity to find some of the most unspoiled and beautiful landscapes in the region. Jost Van Dyke offers many sheltered bays and is dotted with beautiful hidden beaches. Enjoy lunch at one of the relaxing bars or restaurants and top it off with a visit to ‘Bubbly pool’, the island's naturally foaming sea pool!

With a Sailo yacht or catamaran charter, explore this stunning Caribbean destination at your leisure. Coast hop around Tortola, the biggest island, visit the Little Sisters, or head to remote Angeada for true seclusion.

The US Virgin Islands (USVI)

The US Virgin Islands have an unmistakably American flavor and attract American families escaping the winter and looking for some fun in the sun. When it comes to sailing vacations, the USVI’s offer a fantastic choice of locations for Caribbean boat charters.

St. Thomas is known as a premier yacht charter marina in the Caribbean and offers a host of beautiful beaches and snorkelling opportunities. Why not support local business with one of Sailo’s family run private boat tours and head to Brewer’s bay for some of the best snorkeling and a chance to see Turtles and rays.

Get on one of the yacht charters in St. Thomas and cruise to Frydendal, small laid-back settlement of serene beaches and rich marine life. Coki Beach provides some of the best diving on the island. For more adventure places in USVI, explore the famous Wreck of Cartanza, at Shipwreck Cove on Buck island. Just one of the many stunning shipwrecks and coral reefs you can discover by snorkel or scuba in the USVI's.

Strictly speaking Bermuda isn’t in the Caribbean, but she maintains that tropical vibe. Lazy days on beautiful pink sandy beaches, fantastic fishing and friendly and laid back locals. To all intents and purposes, this is the Caribbean! Sailing in Bermuda means less in the way of island hopping, and more fishing charters or exploring shipwrecks with snorkels or scuba gear. With a Bermuda private yacht charter you can explore the many islets along the coast and enjoy an unforgettable game fishing trip.

The Windward Islands

The southern section of the Antilles includes St Lucia, Grenada, Barbados, Martinique, Trinidad and Tobago and St Vincent and the Grenadines. These islands offer diverse Caribbean experiences, and a mixture of cultures and landscapes. The southern Caribbean also sees less hurricanes, making the Windward Islands an appealing option for an all year round Caribbean yacht charter.

St Vincent and the Grenadines makes a great base, offering east sailing plus access to St Lucia or Grenada. Sailo offers fantastic flexible options for either bareboat yacht charters, or for a more stress free experience, a captained choice enabling you to relax and fully enjoy your Carribean experience.

The Leeward Islands

The Leeward islands include the Virgin Islands, St Kitts and Nevis, Guadeloupe and Antigua and Barbuda. Experience colonial influences from the British, Dutch and French and plenty of local flavor added into the mix. Sailing the Leeward Islands offer countless smaller islands to explore and often perfect sailing conditions, making them a perfect yachting destination.

With a Sailo Caribbean catamaran charter in the Leeward Islands, you’ll be able to experience these stunning sailing vacations at your leisure.

For a cultural hit, Nelson’s Dockyard National Park is a restored marina and is one of Antigua’s top sightseeing attractions. In the remote southeast, Half Moon Bay is great for both snorkeling and body surfing in it’s calm waters.

Whatever your itinerary, Sailo has everything you need to help plan your tailor made, flexible Caribbean experience.

Our Favorite Sailing Itineraries in the Caribbean

  • Itineraries

BVI Yacht Charters from Tortola

Starting Location

sailboat charter caribbean

Start in Tortola to clear customs and pick up everything you might need for the next week sailing. This itinerary is popular and considered by many one of the best sailing holidays in the Caribbean that you can plan for!

Norman Island

  • Previous stop Next stop

8 NM from last stop

sailboat charter caribbean

Your first stop is the Norman Island. Sail around until you find the perfect spot to jump in the water and to cool off. Drop anchor and enjoy lunch at one of the restaurants on the beach. Most of our BVI yacht charters are equipped with snorkeling gear, perfect to explore the caves of this rocky island. Once you pick one of our Caribbean yacht charters, make sure to check with your boat representative what gear will be available on board for your trip.

Cooper Island

9 NM from last stop

sailboat charter caribbean

Cooper Island is the next destination to test your snorkeling gear and capture unforgettable underwater memories for a lifetime. Sea turtles are also frequent visitors to these waters. Off the southwestern coast of the island is located one of the most popular diving spots in the BVI’s - the “Wreck Alley” - with four sunken ships transformed in amazing marine life habitats.

Salt Island

2 NM from last stop

sailboat charter caribbean

Your snorkeling and scuba adventure on one of our BVI yacht charters continues at Salt Island. The most notable attraction is a big, complete wreck that you can explore underwater.

Trellis Bay

6 NM from last stop

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Pull into Trellis Bay - home to popular full-moon parties and other exciting nightlife. Trellis Bay Market on the western side of the island is a good spot for fresh provisions. Go for a stroll to check the local art shops and stop for a drink or a nice lunch at the De Loose Mongoose. For a snorkeling afternoon trip, check out the northern side of the cay.

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The Virgin Gorda Baths are an exquisite and unique natural formation. These huge rocks and the surrounding mini coves are great to explore above and underwater, or even climb. Moor your BVI catamaran charter (or yacht if that’s your choice) at the Devil’s Bay Fort Point and spend a great day in water. The nearby Devil's Bay local restaurant/bar is just a short walk away.

  • Previous stop

10 NM from last stop

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Your trip loops back around to the origin city of Tortola. Get reacquainted with dry land around the town before heading back home. We hope this itinerary will make one of your best sailing holidays in the Caribbean on one of Sailo’s BVI yacht charters!

Sailing the Virgin Islands

Starting Port

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Come a few days early (or save time at the end of your trip) to visit the beautiful island of St. Thomas. Gather all your supplies for the next week of sailing on your USVI catamaran charter through the charming Virgin Islands.

Christmas Cove, Great St. James

6 NM from last port

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The turquoise waters at Christmas Cove are perfect for an afternoon swim and snorkel post short sail from St. Thomas. The calm waters of this protected cove are a National Marine Sanctuary where you will see lots of fish, sea turtles, and friendly stingrays. This location is perfect for overnights on any of our Caribbean yacht charters.

Caneel Bay, St. Johns

4 NM from last port

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Drop anchor on your USVI catamaran charter and visit the Caneel Bay Resort, which was built on the site of an 18th century sugar plantation. Bring our your inner "foodie" and visit the Beach Terrace for buffet-style offerings. Feel free to walk the grounds of this luxury beach resort while enjoying the sparkling lights of St. Thomas on the distant horizon, before heading back to your private yacht.

Jost Van Dyke

6.5 NM from last port

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Jost Van Dyke is one of the finest among the Caribbean beaches with its lively bars, comfortable hammocks, and strangers that will be your best friend by the day's end! After a day spent on the beach sipping rum cocktails, Foxy's Tamarind Bar and Grill is a favorite of boating enthusiasts enjoying their time on Sailo’s BVI yacht charters. Enjoy their great local food, Friday and Saturday barbecues, flying fish sandwiches, grilled fresh fish, and lobster for dinner.

16 NM from last port

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Green Cay is an exciting dive and snorkel site which has a series of pinnacles covered with brightly colored sponges and branching hydroid that shelter and abundant marine life. From the stunning coral beach you can walk to a small shipwreck of a more modern-looking boat. Before arriving on one of our BVI yacht charters at Marina Cay for the night, make one last stop at Sandy Cay, a picture-perfect little gem in the ocean, surrounded by white sandy beaches speckled with clusters of rock, green vegetation, and two lonely coconut palms. Tourists from all over the world come here on their Caribbean yacht charters to enjoy sunbathing, excellent snorkeling, and picnics with a view. Marina Cay, your stop for the night, is a flower-covered eight-acre island ringed by a powdery white sandy beach and sheltered by a lagoon with calm and warm waters. Enjoy a mellow night on the deck of your USVI catamaran charter with drinks and a dinner on board.

Spanish Town, Virgin Gorda

5 NM from last port

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Moor your boat and explore the famous Baths, with the scenic boulders and the caves open to the sea. Enjoy the day snorkeling or diving the Wreck of the Rhone, famous from the movie "The Deep". Spanish Town is the perfect overnight stop for all sailing holidays in the Caribbean that include Virgin Gorda island, offering plenty of options for shopping and dining around the harbor.

North Sound, Virgin Gorda

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Dog Islands are a small group of islets in the Sir Francis Drake Channel. They are part of BVI’s Marine National Park and Seabird Refuge making them great diving and snorkeling spots. After an activity-packed day, visit The Bitter End Yacht Club and dine at the Clubhouse Steak and Seafood Grille, a casual, yet elegant restaurant located right on the water.

20 NM from last port

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On your way to Norman Island stop at Peter Island and explore one of the most beautiful beaches in the Caribbean: Deadman's Bay. It’s a great snorkeling spot and also a good option for a fresh lunch right on the beach. If you're looking for a quiet stretch of sand, take a walk to the secluded Honeymoon Beach at the tip of the peninsula. Once you drop anchor on one of Sailo’s BVI yacht charters at Norman Island (your overnight stop), try snorkeling around the 3 water-level caves at the base of cliffs. At the end of the day you can enjoy a casual dinner and a fun happy hour at the famous floating bar and restaurant Willie T’s.

St. Thomas, USVI

19 NM from last port

sailboat charter caribbean

Your final destination is the delightful Frenchtown in St. Thomas. Boating enthusiasts sharing memories from their sailing holidays in the Caribbean recommend this small quaint town as home to some really great casual restaurants. Here you will make lots of friends as the bar is always filled with a crowd of very friendly folks. A perfect dining experience to conclude the perfect vacation on a Sailo USVI catamaran charter!

Island Hopping from Road Town, Tortola

Starting point

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Choose one of Sailo’s Caribbean yacht charters in Tortola and set sail for fun and relaxed trip, hitting all the prime spots in the British Virgin Islands.

NORMAN ISLAND

8 NM from the last port

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Start your adventure on one of our BVI yacht charters on Norman Island, an uninhabited rocky island, considered by some one of the hidden gems of the British Virgin Islands. Time to grab your snorkeling gear and explore the bountiful marine life or swim in the spectacular coastal caves.

COOPER ISLAND

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Then you will visit the Virgin Gorda. Here there is opportunity both for Hiking and beach views. If you want to try both, you can hike along the boulders that end on a beautiful white sand beach.

VIRGIN GORDA

16 NM from the last port

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A must on your to do list when sailing on one of our BVI yacht charters is a stop at Virgin Gorda. Go for a hike along the boulders or relax on the picture-perfect, white sand beach.

JOST VAN DYKE

20 NM from the last port

sailboat charter caribbean

On your way to Jost Van Dyke make a stop to visit Guana Island - famous for the seven different white powdery beaches. Go snorkeling the reefs, relax in a hammock, or set up your own private picnic on land. And if you are in the mood for a walk, explore the tropical forest. Then set sail to the smallest of the four BV Islands - Jost Van Dyke - the perfect stop with an overnight to join the happy, laid-back crowd at the Soggy Dollar Bar or at Foxy’s. Drop anchor in White Bay and don’t miss your chance to try one of the signature rum cocktails at Foxy’s!

CANE GARDEN BAY

6 NM from the last port

sailboat charter caribbean

Don’t miss your chance to stop and enjoy the Sandy Cay - a deserted island with a fantastic beach where you can relax and take in the breathtaking tropical view. Drop anchor and go for a swim or grab your snorkeling gear and explore the crystal clear Caribbean waters. After lunch, set sail to Cane Garden Bay on Tortola for your overnight anchorage.

15 NM from last port

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Head back to Road Town Tortola for the end of your journey. We hope you had an amazing time on one of our BVI yacht charters and we hope to see you soon back on the water!

British Virgin Island - Sailing Holidays in the Caribbean

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Get aboard on one of Sailo’s BVI yacht charters in Road Town and start your tropical nautical adventure!

sailboat charter caribbean

Set sail to your next stop at Bight Bay (formerly known as Man of War Bay). This sheltered inlet is perfect for your first overnight. Explore Norman’s island water level caves and go snorkeling in the crystal blue water.

PETER ISLAND

3 NM from the last port

sailboat charter caribbean

Your next stop - Peter Island - is famous for some of the best beaches in the British Virgin Islands. Drop anchor at Little Harbour: a quiet spot usually not so crowded. White Bay and Key Bay are the best anchorage spots on the south shore. Hop off and try the local Caribbean cuisine.

SALT ISLAND AND COOPER ISLAND

sailboat charter caribbean

Spend the day exploring these two little charming islands. Salt is famous for the Wreck of the Rhone and the surrounding reefs - a spectacular snorkeling and diving spot. Cooper island has a protected anchorage, picture-perfect white sandy beaches and some of the best snorkeling sites in the BVIs (tip: try the crystal clear waters around Cistern point).

sailboat charter caribbean

Your voyage on one of our Caribbean yacht charters must include a stop at the famous Baths. Indulge in the natural jacuzzis and go hiking the beachside boulders for an amazing view of the bay waters.

NORTH SOUND

2 NM from the last port

sailboat charter caribbean

North Sound is a cluster of small islands off the northern tip of Virgin Gorda. Take advantage of the protected anchorage and the calm waters to try out watersports. A fun way to check the area is to glide the turquoise waters on a hobie cat! For a gourmand dinner with a fantastic view, make a reservation at the gorgeous and secluded Biras Creek resort (dress code required).

15 nm from last port

sailboat charter caribbean

Head back to the home port carrying wonderful memories of your sail on one of BVI yacht charters from Sailo!

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    The Caribbean enjoys year-round sunshine and average temperatures ranging between 24°C (75°F) and 32°C (90°F) making it a hugely popular destination for yacht charters. The climate on most of the islands is tropical, but moderated to a certain extent by the prevailing northeast trade winds although they are often warm and moist.

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