Early Booking Deals – Save up to 50%
Search by Listing Number

Refine search results:

Got a question?

(786) 998-2973

02:00 - 11:00 (Miami, UTC-4)

Supported languages: English

Program Partner

Rated
4.8 / 5.0

to see up to 50% discounted boats

  • Recommended
  • Lowest price
  • Highest price
  • Highest rating

12,000+ yachts

Access to 12,000+ verified boats and experiences in 60 countries and 1,400 different locations.

Offers

Take advantage of many surprise offers.

1 of 4

Showing the range 1-20 of 77 results.

Chartering a Sailboat in the Caribbean

Breath-taking in its beauty, the Caribbean is a world-renowned travel destination. It is a symphony of sun-soaked beaches, vibrant cultures, and pristine waters. Stepping onboard a sailboat charter in the Caribbean is an invitation to a world of tropical splendor. The Caribbean is a sailing paradise, with its spectacular coastlines, diverse marine life, and welcoming marinas. Essential travel tips for your Caribbean sailing adventure include arming yourself with navigational maps, observing local customs, and sticking to safety guidelines. What makes Caribbean sailing special is the sense of discovering a new island paradise every day. Expect turquoise waters, balmy nights, and a kaleidoscope of fascinating cultures. Get set for an unforgettable journey into the heart of the Caribbean. Enjoy breath-taking sunsets, meet friendly locals, and catch sight of exotic wildlife from the comfort of your sailboat charter in the Caribbean.

Why choose the Caribbean as the ultimate destination for a sailboat charter?

The Caribbean offers an unparalleled sailing experience. A yacht charter in the Caribbean is an open invite to explore an archipelago of over 700 islands, each unique in culture, cuisine, and natural beauty. In the Caribbean, every journey is an adventure.

How to get to the Caribbean?

Getting to the Caribbean is easy. Major airlines like American Airlines, Delta, and British Airways have daily flights to different islands in the Caribbean. There are also numerous cruise lines servicing the region if you prefer seafaring travel.

What are the popular destinations and routes for a sailboat charter in the Caribbean?

From the BVI's azure waters to Grenada's stunning beaches, there's no end to unforgettable experiences in the Caribbean. Popular sailing routes include the Leeward Islands and Windward Islands, known for their awe-inspiring vistas and abundant marine life.

What is the best time to charter a sailboat in the Caribbean?

The Caribbean sailing season runs from November to July, with the best weather for sailing from mid-December to mid-April. Calm sea conditions and steady winds make this period ideal for a sailboat charter in the Caribbean.

How is the weather and sailing conditions in the Caribbean?

The Caribbean boasts warm tropical climates year-round. Expect pleasant temperatures, manageable winds, and minimal rainfall during the sailing season. With north-easterly trade winds providing consistent sailing conditions, the Caribbean is a sailor's paradise.

How to explore the history and culture of the Caribbean?

Immerse yourself in the Caribbean's rich history through its historical landmarks and museums. Sample local dishes like jerk chicken, enjoy rum tasting tours, or join in the infectious rhythms of calypso music to get a true taste of the Caribbean culture.

What are the top attractions and outdoor activities in the Caribbean?

Beyond sailing, the Caribbean offers a plethora of outdoor activities. Explore the region's dynamic cuisines, enjoy its vibrant nightlife, discover stunning natural landscapes, indulging in watersports, or even just lazing on its sun-kissed beaches. There's always something magical to experience in the Caribbean.

What are the best marinas and anchorages in the Caribbean?

Whether you're seeking an untouched anchorage or a fully serviced marina, the Caribbean has it all. Popular choices include the Rodney Bay Marina, Yacht Haven Grande in St. Thomas, and St. Kitts' Christophe Harbour.

Should I rent a sailboat in the Caribbean with or without a skipper?

The choice to charter a boat with or without a captain in the Caribbean depends on your sailing experience and comfort level. A knowledgeable skipper can enhance your sailing holiday, showing you lesser-known gems. For experienced sailors, a bareboat charter can offer the freedom to explore at your own pace.

Should I rent a sailboat in the Caribbean with or without a crew?

If you're looking for a truly indulgent Caribbean sailing experience, charter a crewed yacht. A professional crew can take care of everything, from navigation to meal preparation, allowing you to relax and marvel at the Caribbean's beauty.

What license do I need to charter a sailboat in the Caribbean?

Many Caribbean islands require a valid International Certificate of Competence (ICC) or an equivalent national boating license if you wish to go for a bareboat sailboat charter in the Caribbean.

What to pack for a sailboat charter in the Caribbean?

Packing for a Caribbean sailboat charter requires some thought. Essentials include lightweight clothing, sun protection gear, water-resistant shoes, and possibly a light jacket for evenings. Entertainment options like books, music, and games are always a great addition.

Our Nearest Destinations to Caribbean

Explore stunning locales for your dream Sailboat Charter adventure in Caribbean.

Yacht Types in Caribbean

Explore choices designed for your upcoming maritime escapade in Caribbean.

Alternative Choices for Sailboat Charter in Caribbean

Find unique alternatives for a personalized maritime experience in Caribbean.

Good to Know about Sailboat Charters in Caribbean & Near Me

Number of sailboats 77 sailboats available
Minimum Price $ 262 per day
Maximum Price $ 8,832 per day
Average Price $ 1,102 per day
ManufacturersBeneteau, Jeanneau, Yacht, RM Yachts
Average length13.62 m (44.68 ft)
Average sleeping capacity7.84
Average cruise capacity7.87

Frequently Asked Questions about Sailing Yacht Rentals in Caribbean & Near Me

How many sailboat are available for charter in Caribbean?

There are 77 sailboats and sailing yachts of various sizes in Caribbean.

How much does it cost to charter a sailboat in Caribbean?

The cost to charter a sailboat in Caribbean is typically between $262 and $8,832 per day, with an average daily price of $1,102.

Private charter with overnight accommodation

The price range for sailboat rental with overnight accommodation in Caribbean is typically between $262 and $8,832 per night, with an average price of $1,102.

How much does it cost to rent a sailing yacht for a week in Caribbean?

The cost to charter a sailboat in Caribbean is typically between $1,837 and $61,822 per week, with an average weekly price of $7,711.

What are the popular sailboat brands in Caribbean?

Popular brands in Caribbean are: Beneteau, Jeanneau, Yacht, RM Yachts.

What are the popular sailboat models in Caribbean?

Popular models in Caribbean are: Moorings 46.3, Sunsail 410, Sunsail 46 Mon, Moorings 42.3, Moorings 52.4, Beneteau Oceanis 48, Sun Odyssey 42 i, Sun Odyssey 440, Moorings 382, Moorings 45.3.

What are the dining options on board a sailboat in Caribbean?

On a sailboat, guests have the option to either purchase their own food supplies or have the boat owner/crew acquire the supplies for them. When there is a crew on board, they typically take care of the cooking. For more information about meal options, please review the listing details.

What is the average number of cabins on a sailboat in Caribbean?

The average number of cabins on a sailboat in Caribbean is 3.23. For larger groups, there are sailboats with up to 5 cabins available for charter as well.

What is the average sleeping capacity on a sailboat in Caribbean?

Sleeping capacity in Caribbean ranges from 6 to 10 persons, with an average capacity of 7.84 persons.

What is the average cruising capacity on a sailboat in Caribbean?

Cruising capacity in Caribbean ranges from 6 to 10 persons, with an average capacity of 7.87 persons.

Can I charter a sailboat as bareboat or skippered in Caribbean?

You can charter a sailboat as skippered in Caribbean.

How many sailing yacht are available for bareboat charter in Caribbean?

There are 76 sailboats available for bareboat charter in Caribbean.

How many sailing yacht are available for skippered charter in Caribbean?

There are 1 sailboats available for skippered charter in Caribbean.

How much does a skipper cost per day in Caribbean?

The cost of hiring a skipper can vary depending on the destination and the boat's owner. In, Caribbean you can anticipate an average daily rate of $190 for a skipper.

What are the popular sailboat charter locations in Caribbean or nearby?

Popular locations in Caribbean and nearby are: British Virgin Islands, Martinique, Grenada, Saint Vincent and Grenadines, Saint Lucia, Guadeloupe, Antigua and Barbuda.

Summary of Cost of Sailboat Charters in Caribbean & Near Me

With overnight accomodationMin. price per dayAvg. price per dayMax. price per day
Sailboat 262 $ 1,102 $ 8,832 $

Contact Us

Our dedicated holiday experts are available seven days a week to assist you.

02:00 - 11:00 (Miami, UTC-4)

Supported languages: English

Help Center

or

Let us call you!

Average response time:

12 minutes

Login or register to unlock offers and discounts!