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A trip to the Caribbean is something almost anyone will enjoy. It is paradise, after all, and the region’s popularity continues to grow year after year – and the ultimate way to explore the Caribbean is by luxury yacht charter. A yacht gives you the power to freely navigate a world of hidden islands, crystal waters, swaying palms and white-sand beaches.

Enjoy the easygoing lifestyle and positive energy that the Caribbean is famous for as you discover what makes these islands some of the most unique places on earth. From the Virgin Islands to St. Kitts, St. Barths to Barbados, Antigua to Turks and Caicos, here you can enjoy a world of charm, culture and flavor, with incredible history, watersports, dining, luxury resorts and more.

You can visit the Caribbean aboard a luxury yacht charter any time of year, but the winter is best – especially around Christmas. Many people enjoy celebrating the holidays and New Year’s Eve on a yacht charter, so if this sparks your interest, contact us for guidance on booking yout Caribbean yacht charter today.


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The Bahamas is a true luxury yacht charter paradise. The archipelago consists of hundreds (some say thousands) of islands and cays. There are three major areas in the Bahamas ideal for a yacht charter: the Abacos, famous for world-class fishing, Eleuthera Island, known for its pink sand beaches, and the…

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Cuba yacht charters

Dreaming of a trip to beautiful Cuba? A luxury yacht charter is the perfect way to see the island. Experience art, culture and the historic charm of Old Havana’s stunning colonial architecture. You’ll also fall in love with Cuba’s exquisite beaches and some of the world’s best offshore cruising. Take…

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British Virgin Islands (BVI)

British Virgin Islands Yacht Charters

For anyone who enjoys fishing, diving, and soaking up the sun on some of the nicest beaches in the world, then the British Virgin Islands (BVI) is a dreamy place to charter a luxury yacht with 26 North. The largest island is Tortola, renowned for its shockingly white beaches, lush…

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The Leeward Islands

The Leeward Islands

If you’re thinking of a luxury yacht charter in the Leeward Islands, keep reading. This group of Caribbean islands is nothing if not diverse. Each island has its own personality, cuisine, and “must-see” sites. Tying them all together is raw beauty – turquoise waters, white-sand beaches, and sunsets that will…

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Dominican Republic

The Dominican Republic is the second-largest country in the Caribbean and by far its most geographically diverse. Together with Haiti, it occupies the island of Hispaniola. “The DR,” as it’s commonly called, is known for warm and hospitable people, astounding nature, intriguing history and rich culture. Exploring the DR by…

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Turks and Caicos

Turks & Caicos Yacht Charters

If you are looking for a luxury yacht charter to sail the Caribbean, one place you must visit is Turks and Caicos. This group of British territories includes 41 islands famous for high-end resorts, turquoise waters, white-sand beaches, and luxury yachts from around the globe. Turks and Caicos sit on…

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Windward Islands

The Windward Islands are the southern larger islands of the Lesser Antilles, just south of the Leeward Island, and they include Grenada, Saint Lucia, and Saint Vincent and the Grenadines. Chartering a yacht in the Windward Islands is an unforgettable experience that combines the natural beauty of the Caribbean with…

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Yacht chartering in the US Virgin Islands (USVI) is a popular way to explore the natural beauty and vibrant culture of this Caribbean destination. With crystal-clear waters, stunning beaches and plenty of opportunities for adventure, a luxury yacht charter in the USVI offers a unique and luxurious way to experience…

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Get Started

There are so many reasons why you should head to the Caribbean and enjoy a holiday just like the many crewed luxury yachts we see each year. There are over 700 islands in this region, and if you want to visit a specific group, you need a vacation planner to help you with your itinerary.

Caribbean luxury yacht charters know that the region can be split into two main areas: the Greater Antilles and the Lesser Antilles. The first is where you can find countries like Cuba, Jamaica, and the Dominican Republic. The second, the Lesser Antilles, is a group of islands that can be divided into the Windward Islands and the Leeward Islands. From here, the Leeward islands include St Kitts and Nevis, the British Virgin Islands, Anguilla as well as Antigua and Barbuda. The Windward Islands, on the other hand, are where Grenada, Barbados, Grenadines, Dominica, St. Vincent, and St. Lucia are located.

Another reason why you should consider a yacht charter trip to the Caribbean is the wonderful climate and year-round sunshine. You can see the coral reefs, palm trees, and untouched beauty in the tropical islands, making the Caribbean your next yachting destination. Plus, there are some delicious cocktails to try, especially with the homemade rum in Cuba!

Now that you are more familiar with yacht charters in the Caribbean, let’s look at some of the top places you can visit before looking at the luxury yacht charters available for your desired dates.

Greece Yacht Charters Itinerary - 26 North Yachts


A Caribbean yacht charter holiday is one of the best decisions you can make for yourself or your family. You can go with your partner, group of friends, extended family or any group you combine. The prices of Caribbean yacht charters vary according to the luxury yacht that you choose – more specifically, its size, style, and age. You can rent luxury yacht charters from 30,000 USD to more than 1,000,000 USD on a weekly basis (minus expenses), in the form of an advanced provisioning allowance (APA). The best way to know the cost of a yacht charter trip in the Caribbean is by contacting us and sharing your wants and needs.

The Caribbean is a famous hotspot for crewed yacht charters, which is why booking your holiday in advance is recommended. Most people know that places like the US Virgin Islands, St Martin St Lucia, St. Barts, and the Bahamas are popular destinations to sail and enjoy due to their fantastic diversity, beautiful and warm climate, and a large selection of yachts for charters that you can rent.

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The warm climate and lots of sunshine make the Caribbean a year-round vacation spot. The best time to visit, sail the waters and explore the destinations is generally December through March. During this period, the weather is temperate and you can spot more luxury yachts in the area and plenty of onshore amenities. Cruising off-season is also great because the islands are less busy and you can see more places without plenty of crowds.

Did you know: While there are six official languages spoken in the Caribbean and a lot more unofficial languages, the current language that charterers speak in English, and you should have no problems communicating with locals in English.

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