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Caribbean pier and yacht and catamaran charter
Caribbean yacht charter sailing in blue sea

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, 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.

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.


Stunning natural beauty from magnificent mountains to unexplored coral atolls.


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. 


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.

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.

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?

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.

Why should I book with Dream Yacht?

Dream Yacht Worldwide is now the world’s leading yacht charter company and offers you:

  • A diverse fleet of yachts with a wide variety of models and manufacturers to suit every type of sailor.
  • We have +60 exciting destinations and we’re a pioneer in finding new sailing grounds.
  • You can be assured of our commitment to customer service excellence.
  • You’ll receive a warm and friendly welcome from our base teams who will share regional tips, recommendations and advice.
  • We’re also a trusted seller of new and used boats and an innovator in charter management options – sailing is our business.

What licenses do I need to hire a yacht and sail myself?

The skipper of a yacht has primary responsibility for the safety of the crew and yacht at all times. Many destinations require just relevant experience demonstrated by a sailing resume.

To charter in the Mediterranean, it is mandatory that you hold a sailing license recognized by the local port authorities for bareboat charters in Italy, Greece, Croatia, Spain, Malta, Montenegro and Turkey. Other destinations that require a license include Madagascar, Seychelles, Thailand, Brazil and Sweden. For Belize, the port authority will issue a certificate of competency and an application is made on arrival.

You must take your proof of competency and original certificate with you on your charter. We advise you to contact our team about your qualifications and destination requirements before booking.

By accepting the yacht contract you are confirming that you and/or members of your crew are capable and competent to sail the yacht in the conditions and cruising area of the charter. We reserve the right not to hand over the yacht if, after inspection, it is the opinion that the charterer is not, or may not be competent to be in charge of the vessel.

What is a skippered yacht charter?

A skippered yacht charter is when you rent one of our boats for you and your guests and a professional skipper sails it for you. No sailing experience is needed.

You will need to choose a yacht with a cabin for your skipper to sleep in as they are responsible for your yacht for the duration of your charter. We will find the skipper for you once you have found your perfect destination and yacht.

You will need to pay for your skipper’s food. You can invite the skipper to dine with you on board or out at a local restaurant.

What is the difference between crewed and by the cabin charters?

Our by the cabin charter charters offer exciting destination tours on a set itinerary crafted by our destination experts. You can book a double cabin and private bathroom and will share the boat with other guests who have booked the other available cabins. You will be looked after by a professional skipper and hostess with itineraries ranging from three to 11 nights. There is a set menu and included meals and drinks vary depending on location.

Can you tell me about your yachts?

Our super premier yachts are less than 12 months old from their first charter date, while premier yachts are less than three years old from their first charter date. Our yachts are well maintained and undergo regular, scheduled technical inspection.

In case of emergency, you can rely on our hotline, at any time, seven days a week. If you experience a technical failure affecting major and important parts of the yacht, we will repair the failure within four hours of receiving your call during working hours (8am to 5pm). If you lose more than four hours (during working hours), we will compensate you for one full day. If the repair takes more than one day, we will provide you with a similar boat or compensate you on a pro-rata basis. If restrictions to this guarantee apply in specific areas, this will be detailed during the charter check-in at the base.

Do I need insurance?

We highly recommend you arrange travel insurance in case you need to cancel for an unexpected reason to cover non-refundable deposits. Please make sure you have personal travel insurance that covers sailing.

We will insure the vessel throughout the charter with first-class insurers against all risks, to provide permission to charter as under contract terms and to cover third-party liability.

The following options are available in limited locations:

  • Security Deposit: This varies on the size of the boat and when the boat is returned without damage it is refunded.
  • Damage Waiver: The charterer agrees to pay a non-refundable damage waiver at the time of booking, as well as a reduced damage deposit on embarkation that is refundable upon completion of the charter should no damage occur.

Ever considered a Cabin Cruise?

As pioneers in the industry, Dream Yacht was one of the first to develop the Cabin Cruise concept. It’s an ideal choice for solo or couples travelers seeking relaxed adventure, exotic destinations, and unique local cultures in an intimate, social setting – in comfort at sea.

Our promise

Private accommodations

Comfortable and private standard double cabins with ensuite bathroom

Curated itineraries

Experience world-class destinations, local culture and excursions with our expertly curated itineraries


An affordable and intimate experience without the need to book an entire yacht or provide sailing qualifications

Vetted crew

Enjoy our professional crew with a strong local knowledge and friendly service

Full board meals

Enjoy fresh and delicious cuisine prepared and served daily

Choose your mood

Relax on deck socializing with fellow travelers, kayak or snorkel from your yacht, or enjoy exploring ashore

Get inspired! #MyDreamYacht

Follow our customer’s journeys & then get ready to share your own amazing experiences on Instagram

What’s new?

Stay up to date with news and events or get some inspiration for your next yacht charter and pick up useful tips by reading our latest blogs.
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