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Caribbean Yacht Charter

For a truly relaxing vacation, enjoy the easy sailing conditions, pleasant year-round climate and world-renowned cruising grounds of a Caribbean yacht charter.

What’s on this page


  • Palm-fringed beaches
  • Relaxed Caribbean charm
  • Year-round warm weather

Caribbean Sailing Vacations

Caribbean yacht charter sailing in blue sea

Sail between stunning paradise islands, each with its own distinct character, and experience a friendly welcome from locals and international sailors alike in one of the region’s many famous beach bars.

From beautiful sandy beaches, step into the warm Caribbean sea and dive or snorkel among abundant marine life, or take a trip into the lush, verdant hills for a hike to discover some breathtaking views.

Sailing the Caribbean also gives you the opportunity to taste the freshest seafood with a Creole twist, including the much-prized lobster and conch. And don’t forget to try the local rums, which feature on many Caribbean cocktail menus. 

Away from the beach bars, explore the rich history of the Caribbean’s many islands, Martinique, Antigua or the Spice Island of Grenada, where fierce pirates used to roam. Whether you sail the British Virgin Islands or charter a yacht in the Grenadines, you won’t be far from a picture-perfect destination with our Caribbean boat rentals.

Choose a destination below to discover more

Easy sailing, verdant hills, beautiful sandy beaches and paradise islands are yours to discover when you charter a yacht from one of our eight bases throughout the Caribbean, including Belize, the Virgin Islands and Antigua.

US Virgin Islands

Enjoy sailing one of the world’s most wonderful cruising grounds.

St. Martin

An attractive mix of chic resorts and unspoiled natural beauty.


Explore flawless beaches, pretty villages, lush rainforests and rugged peaks.


Let favorable winds carry you to tranquil cayes and beaches.


Escape to a more authentic, less-traveled and stunningly beautiful Caribbean.


Journey to unspoiled beaches, spectacular coral reefs and lush rainforests.

British Virgin Islands

Hop from lively resorts to uninhabited islands with dazzling beaches.


Sail between paradise islands, beautiful coral reefs and hidden coves.

Top things to do in the Caribbean on a sailing vacation


Sail from our Jolly Harbour base and choose from 365 beaches. Picnic at the undeveloped Pinching Bay, snorkel Deep Bay or follow Nelson’s footprints at English Harbour. You can also sail to the nearby islands of St. Kitts, St. Barths, St. Martin and Montserrat.

British Virgin Islands

From our base on Tortola, discover the fantastic islands of the BVIs, taking in the Baths rock formations on Virgin Gorda, Jost Van Dyke’s lively beach bars and Anegada’s fresh lobster restaurants, or dive the wreck of the historic RMS Rhone. 

US Virgin Islands

Discover the amazing coast of St. John with its white sand beaches and sparkling waters. Head to St. Croix and Water Island too, before exploring the coast of St. Thomas, where we have our base at Compass Point Marina.


Sail from Port Louis Marina and discover the Spice Island of Grenada. Snorkel the underwater sculptures at Petite Martinique and taste the rum on Carriacou. Swim with rays and turtles at Grand Anse Beach or sail on to Union, Mayreau, Tobago Cays and Bequia


Start your charter from Marina Base Fort and discover the marine life at Cousteau’s Pigeon Island underwater reserve. Take in the Les Saintes archipelago with its fort and snorkel spots, Marine Galante’s traces of past industry, or head to Dominica’s waterfalls.


Our Le Marin base is ideal to explore Petite Anse d’Arlet and Fort de France, as well as the Grenadines. Island hop to St. Lucia and Soufrière’s volcano, St. Vincent and the archipelago of Tobago Cays – the sparkling natural jewel of the Caribbean.

St. Martin

From Marina Fort Louis, absorb the cultural mix of French, Dutch and Creole influences of this special island. Sail the nature reserve surrounding Tintamarre and visit Pinel Island and Prickly Pear. Nearby is St. Barths with its chic boutiques and jet set crowd.

When is the best time to visit the Caribbean?

Caribbean guest enjoying vacation at the sea

The best time to visit the Caribbean is between December and April, when temperatures average 84ºF. The Caribbean climate is warm year-round and drier between January and April.

May and November are the shoulder months of the Caribbean hurricane season, which runs between June and October, when the weather can get wetter and windier. 

Sailing trips in the Caribbean to suit your budget 

If you sail the Caribbean in the low season, the flights are generally cheaper and your choice of seat availability is wider. 

Sailing the Caribbean during high season offers a wider choice of amenities and itinerary options, as all the beach bars and restaurants are open.

What are the sailing conditions in the Caribbean?

The sailing conditions in the Caribbean are generally calm with easy sailing and often line of sight navigation where you can see the island you are sailing to. 

Islands tend to be close together and voyages can be short, or you can sail longer passages to explore more Caribbean islands on your yacht charter. It’s totally up to you.

Caribbean wind systems

The Caribbean wind systems include northeasterly trade winds, which blow in the Caribbean during the winter months, providing a welcome relief from the humidity. 

The famous and exciting Christmas wind comes in mid-December, with gusts reaching 20-25 knots; a popular treat for sailing enthusiasts.

What are the mooring fees in the Caribbean?

Caribbean mooring fees depend on the time of year you sail, destination and vacation preferences. 

The good news is there are plenty of opportunities to anchor for free in the Caribbean, or at least in exchange for the cost of a drink and meal.

If you plan on using marina facilities, it’s wise to reserve in advance in the high season where you can, or arrive early in the morning to avoid disappointment. 

It’s likely you will have to pay a fee depending on your yacht size, usually priced per foot, and this can vary depending on the island you’re visiting and the marina. Upmarket islands and marinas are more expensive.

You can find low cost Caribbean mooring balls in many popular anchorages and national parks. You may find the price includes extras, such as ice, although some have time limits or restrictions for conservation reasons.

What are the national park fees in the Caribbean?

The national park fees in the Caribbean mean you are likely to have to pay to enter marine parks or nature reserves. These fees support important conservation projects, so we can continue enjoying these special places for decades to come.

Caribbean crystalline waters

Useful information for Caribbean yacht charters

Caribbean guest enjoying vacations in a yacht charter

What is the currency in the Caribbean?

You will find that the currency in the Caribbean varies from island to island, including the Euro, US Dollar and East Caribbean Dollar, to name just a few.

What is the Wi-Fi connection like in the Caribbean?

The Wi-Fi connection and internet access in the Caribbean can vary from island to island. Many bars, restaurants and marinas have Wi-Fi, but it may not be strong enough for photo or video upload or download.

You can buy a local SIM card, but you may find they are expensive.

What is the best way to get to the Caribbean?

The best way to get to the Caribbean is to fly from the many US airports that offer direct flights to the countries where we have our bases. 

Our Caribbean yacht charter bases are a short distance away from the airport and near main supermarkets and places of interest.

Discover Caribbean charter vacations with Dream Yacht Charter

Caribbean yacht rentals for sailors

If you can sail, you can browse our available destinations for your Caribbean yacht rentals and design your own itinerary, provision the boat yourself and sail at your own pace.

Captain only Caribbean charters

If you haven’t got sailing experience, you can still sail the Caribbean with one of our skippered charters. The skipper will sail the yacht for you, while you relax with your guests.

Caribbean crewed charters

Hire our all-inclusive premium yachts with professional crew for a luxury Caribbean sailing vacation, with the itinerary and meals tailored to the preferences of you and your guests.

Caribbean vacation packages

If you’re looking to relax, take a look at our destinations for organized Caribbean stateroom charters. Book a double cabin with private bathroom and let our captain take you on a tour of the region’s highlights. There will also be a chef to serve you all your meals.

Caribbean sailing itinerary

Our local base teams have all the expert knowledge to help you plan your Caribbean sailing vacations. They’ve prepared exciting Caribbean yacht charter itinerary suggestions, whether you want to sail for a week, 10 or 14 days. Choose your destination and see our itinerary ideas.

With so many Caribbean islands to see, you might want to consider sailing for longer and explore more.


Antigua, Jolly Harbour Marina

Base Guide Bareboat pdf 554.53 KB
Catering Bareboat pdf 684.01 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Itinerary Bareboat pdf 257.71 KB
Provisioning Beverage Bareboat pdf 348.77 KB
Provisioning Bareboat pdf 270.26 KB
Sailing Resume Bareboat doc 87.50 KB

BVI, Hodge's Creek Marina

Base Guide Bareboat pdf 566.07 KB
Base Guide Cabin pdf 504.35 KB
Crew List Bareboat doc 104.00 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Sailing Resume Bareboat doc 87.50 KB
Special Diets Cabin pdf 92.75 KB

Grenada, Port Louis Marina

Base Guide Bareboat pdf 424.69 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Hotels Near Base Bareboat pdf 103.23 KB
Provisioning Price List Bareboat xls 146.50 KB
Sailing Resume Bareboat doc 87.50 KB

Guadeloupe, La Marina Bas du Fort

Base Guide Bareboat pdf 739.24 KB
Base Guide Cabin pdf 753.19 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Provisioning with pdf 5.70 MB
Sailing Resume Bareboat doc 87.50 KB
Special Diets Cabin pdf 92.75 KB

Martinique, Le Marin

Base Guide Bareboat pdf 689.40 KB
Base Guide Cabin pdf 424.01 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Provisioning with pdf 5.70 MB
R I B Bareboat doc 35.00 KB
Sailing Resume Bareboat doc 87.50 KB
Special Diets Cabin pdf 92.75 KB

Placencia, Roberts Grove Marina

Base Guide Bareboat pdf 460.41 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Provisioning List Bareboat xlsx 59.25 KB
Sailing Area Restrictions Barebpoat pdf 225.07 KB
Sailing Resume Bareboat doc 87.50 KB
Temporary Master Application Bareboat pdf 165.93 KB

St. Martin, Marina de L'Anse Marcel

Base Guide Bareboat pdf 530.26 KB
Base Guide Cabin pdf 496.60 KB
Guests List And Passport Info Cabin xlsx 20.79 KB
Sailing Resume Bareboat doc 87.50 KB
Special Diets Cabin pdf 92.75 KB
Wine List Autorisation Form pdf 199.07 KB
Wine Price List Catalogue Boat pdf 7.04 MB

St. Thomas, Compass Point Marina

Base Guide Bareboat pdf 558.42 KB

What is the cancellation policy for Sail Share?

We highly recommend you arrange travel insurance in case you need to cancel for an unexpected reason to cover non-refundable deposits.

Our Sail Share cabin cancellation fees are:

  • More than 90 days before original embarkation date: 25% of the charter fee
  • 89 – 60 days before original embarkation date: 50% of the charter fee
  • 59 – 30 days before original embarkation date: 75% of the charter fee
  • Fewer than 29 days before original embarkation date: 100% of the charter fee

How flexible is the itinerary for a Sail Share charter?

Our yacht itineraries are designed by our destination experts and are set to showcase the best of the destination’s highlights. They are set and not flexible, even if you book all the cabins.

What happens if the weather changes while sailing on a Sail Share charter?

The skipper may decide to change the itinerary if there is bad weather.

Can I choose which cabin I want when I book a Sail Share?

Choose a double cabin with shared bath, or private bath for an additional fee.

Are there child or age restrictions for Sail Share?

Minimum Age: 16 years old

Get inspired! #MyDreamYacht

Follow our customer’s journeys & share your own amazing experiences on Instagram

Absolutely amazing! Fred + Isabelle were so accommodating and did so much for us. Isabelle’s food was incredible. Thanks so much!


Exumas Cabin

Excellent. Very professional and great service!


Antigua Bareboat

Just what we needed coming out of a year of lockdown, to see new places and connect with nature. Highly recommended for your next sailing adventure!


St. Martin Bareboat

Excellent cruise and very good stay. Skipper attentive, very pleasant and very professional.


Guadeloupe Skippered

Just returned from another fantastic sailing week at your base in Pula and I would like to thank everyone involved for making this possible on such short notice and without any problems.


Croatia Bareboat

The marina itself is a perfect starting point with great facilities! The Lagoon 42 was in good condition and the skipper was amazing and very knowledgeable of the area.”


Spain Skippered

What an AMAZING experience. We’ve just returned from a week long skippered charter from Corfu, sailing around the beautiful islands of the Ionian. Paxos, Antipaxos and Corfu Old Town were beautiful and the secluded bays we had the pleasure of visiting thanks to our local skipper, Nicholas, were simply overwhelming. Fly and flops are no longer for us – we’ll be chartering with DYC for the foreseeable future.


Greece Skippered

Our group of 10 had an AMAZING time in French Polynesia from May 21-28, 2022! The food was amazing, our captain and chef, husband and wife: Henry and Mehee (sp), were incredible and the whole experience on board was a dream! We can’t wait to book another trip through DYC


Tahiti Crewed Premium

DYC provided a great sailing experience for my extended family on 2 monos out of Scrub Island. The boats were in great shape and preformed perfectly and the staff were friendly and helpful. Having worked for a number of charter companies over the years DYC is one of the best.


British Virgin Islands Bareboat

Baja is my favorite place now. There was something for everyone: sailed under northerlies with mostly calm evenings, snorkeled, fished, bummed it on the sandy beaches, enchanted by pelicans feeding, greeted by the barking sea lions and explored the Ispiritu Santo island geology. DYC La Paz base provided competent professional support with a well provisioned and maintained boat. We were nourished well by an onboard cook arranged with DYC freeing us all for more play. A vacation and an adventure connected with nature.


Mexico Crewed Premium

All staff were fantastic and made our trip very memorable. Incredibly friendly and welcoming, the food was amazing. The service throughout the trip was always first class!


Thailand Cabin

Absolutely recommended. Perfect service and set up. Will charter again and will recommend Dream Yacht Charter anytime.


Turkey Bareboat

I just returned from 3 weeks of amazing sailing with my family on one of your catamarans in Sardinia. I would like to express my thanks to our skipper Simone and Daniela, our hostess.


Sardinia Bareboat

For a first cruise as a skipper, the Mediterranean is great. The Dream Yacht Charter service is too!


France Bareboat

We had an incredible trip and actually got engaged on the first night of our sail! We will certainly be back one day. Thank you for getting us ready for our charter. We were definitely beginners but he gave us a very thorough but very easy to follow training and it gave us a lot of confidence.



The on board experience was way beyond our expectations. Isabelle provided exceptional three course meals. We could not believe her creativity and delicious meals. Thomas was an excellent skipper. He was always on the lookout for our needs. Thanks guys!” Spira, New Caledonia bareboat with crew charter


New Caledonia Bareboat

Yet again another fantastic sail with another great crew. Thanks again to a great captain and cook. Was totally fantastic.


Seychelles Easy Crewed

It’s always a pleasure sailing with DYC in the UK. Great team, great boats, great sailing. Very flexible and work hard to make your trip a success. Many thanks.


Brittany Cabin

Unforgettable spots to snorkel and beaches. Very experienced crew. Highly recommend.


No Country Selected Bareboat


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