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
Caribbean Sailing Vacations
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, including Cuba, 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.
Caribbean Yacht Charter
Easy sailing, verdant hills, beautiful sandy beaches and paradise islands are yours to discover when you charter a yacht from one of our nine bases throughout the Caribbean, including Cuba, the Virgin Islands and Antigua.
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.
A Cuba yacht charter from our base in Cienfuegos offers a chance to visit the remote cays of the Canarreos archipelago. Visit Cayo Largo’s impressive Playa Sirena beach, Cayo Campos’ inquisitive monkeys and the pink sands at Cayo Rosario
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.
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.
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.
When is the best time to visit the Caribbean?
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.
Useful information for Caribbean yacht charters
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
BVI, Hodge's Creek Marina
Cuba, Cienfuegos, Club Cienfuegos – Punta Gorda
Grenada, Port Louis Marina
Guadeloupe, La Marina Bas du Fort
Martinique, Le Marin
Placencia, Roberts Grove Marina
St. Martin, Marina de L'Anse Marcel
St. Thomas, Compass Point Marina
FAQSee all our FAQs
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
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