Sailing boat rentals in the Caribbean

Destination
Dates
Add your dates
Type of boat charter
With or without a captain
Price per day
0 - $1,250+
Length of boat
0 - 196+ ft
Engine power
0 - 400+ hp
Year of manufacture
2002 - 2023
Distance
50 Max MI
1 sailboats available

Dynamique - 47 | 6 people (14.1m)

Caribbean
4
With captain

From $302 per day

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Sailboat Rental in the Caribbean

The Caribbean is an idyllic island destination with a vibrant and authentic culture. With a warm tropical climate through winter, steady sailing winds and a range of some 7,000+ outstanding islands to hop between, you can choose everything from uninhabited and remote outcrops to bustling port towns with a swinging nightlife for your sailboat rental in the Caribbean. Although there's plenty of smooth and easy sailing to be had in the Caribbean, more adventurous opportunities await in areas like St. Martin, with open-water stretches and remote anchorages. You can choose from a wide variety of Caribbean sailboat rentals at good prices for your next sailing adventure.

A sailing paradise, paired with rich cultures, cuisines and traditions, the Caribbean is full of adventures and beautiful stretches of coastline where you can sail with your friends and family. No matter where you go, we can guarantee you a holiday full of adventure, when you go sailing in the Caribbean. Sail the British Virgin Islands and anchor in idyllic bays where you can stop for lunch or a cocktail on the beach. Snorkel with the tropical fish and turtles in the Bahamas and even encounter a swimming pig, or two! (Yes! We’re not joking!) Let yourself go as you sail with the wind in your hair and admire a constant panoramic view of breathtaking nature at its best. Rent a sailboat in the Caribbean!

How to Rent a Sailboat in the Caribbean

Sailboat rental in the Caribbean is easy and will only take a few minutes. Many visitors will choose to charter a sailboat for a week or more, either with a skipper or without, to fully explore the best of the Caribbean. As a region of colonial heritage, each island offers a unique blend of cultures. Whether that's Anglophone areas like the British Virgin Islands or Francophone Guadeloupe, it's best to choose one of the island areas to explore. You can choose to circumnavigate larger islands like Puerto Rico or stick to archipelagos and island-hopping.

How much does it cost to rent a sailboat in the Caribbean?

There are many different factors that can affect the cost of sailing the Caribbean seas, including the size, capacity, and type of boat, the season when you want to sail, the duration of your trip, and the number of people on board.  The price of Caribbean sailboat rentals will also be affected by whether or not you want to set sail with a skipper, as well as which extra services you want to add to your charter.  For example, you can usually choose to add a crew and watersports equipment to your charter for an additional charge.  

In general, though, sailing in the Caribbean will cost you at least $363 per day or $2542 per week in high season, and a minimum of $186 per day or $1304 per week in low season.

Can you go sailing in the Caribbean with or without a skipper?

Yes, it is possible to find a sailboat rental in the Caribbean either with or without a skipper.  However, you must keep in mind that if you want to charter without, you must be in possession of the appropriate licence.Sailing the Caribbean seas with a skipper and maybe even a crew is perfect for those who want a holiday where they only need to sit back and relax, watching as the spectacular shorelines of the Caribbean go past.  However, if you are someone who likes a little more adventure, bareboat Caribbean sailboat rentals where you can be the captain of your own boat will be a dream come true.

Sailing areas in the Caribbean

The Caribbean is a sailors playground, with an unlimited number of routes and potential itineraries. The British Virgin Islands may offer the best flexibility, with many islands within close distance from each other, offering plenty of opportunities to sail between 25 islands and take day excursions between glorious beaches and coves to a wealth of well-maintained ports such as Nanny Cay, Inner Harbour and Joma Marina. Alternatively, Grenada, St. Vincent and the Grenadines remains another favourite destination for experienced sailors, with gentle crystalline waters, alluring cays and paradisical islands. You should also consider Antigua and Barbuda, an area famed for its open sea races with plenty of small islands to visit.

Sailing boat rentals in the Caribbean are a popular choice of boat and can be found in the following areas of the Caribbean:

Itinerary Ideas in the Caribbean

Lacking inspiration for your sailboat rental in the Caribbean or simply need some tips? Check out our Nautal blog for sailing routes around the BVI, Martinique, Guadeloupe and much more! We calculate nautical miles in our routes and give restaurant recommendations in addition to other random facts and cool things you can do in the area.

Climate and Sailing Conditions in the Caribbean

Our favourite time of year is spring and early summer, from March to June, when the islands are in bloom and are a pleasure to sail. The trade winds are perfect at this time of year, though Christmas and Thanksgiving are also popular times of year for sailboat rentals. We do not advise sailing in August and September as this is known as hurricane season and various areas are not safe during this time of year. 

When is the best time to rent a sailboat in the Caribbean?

As long as you avoid sailing in the Caribbean between August and September, you are bound to have a fantastic time.  Although many people look for a sailboat rental in the Caribbean over the winter months, we actually advise going in Spring and early summer.  From March until early June, the weather will be perfect for sailing and there also shouldn’t be too many tourists.  The reduced number of people means that you should be able to find better deals on boats.

How to get to your sailboat rental in the Caribbean?

The best way to reach the islands is usually by plane, or alternatively you can rent a sailboat in Miami or in the near Florida and sail to Caribbean areas such as The Bahamas.  Many islands have international airports and you can fly directly or find connection flights. 

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