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Crewed yachts in the Caribbean

Endless Summer III

Endless Summer III


2024 | Length: 65.00ft

Guests: 10  | Cabins: 5   | Crew: 3


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Snapdragon

Snapdragon


2025 | Length: 58.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Emysa

Emysa


2019 | Length: 58.00ft

Guests: 6  | Cabins: 3   | Crew: 2


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Ad Astra

Ad Astra


2020 | Length: 55.00ft

Guests: 10  | Cabins: 5   | Crew: 2


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Sun Daze

Sun Daze


2023 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Zuri 3

Zuri 3


2021 | Length: 54.00ft

Guests: 6  | Cabins: 4   | Crew: 2


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Lola

Lola


2024 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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High 5

High 5


2023 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Katlo

Katlo


2023 | Length: 55.00ft

Guests: 6  | Cabins: 3   | Crew: 2


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Barefoot Bliss

Barefoot Bliss


2024 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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La Vie Est Belle

La Vie Est Belle


2024 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Whiskey Sunset

Whiskey Sunset


2025 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Atlas

Atlas


2022 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Out Of The Blue

Out Of The Blue


2024 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Elysian

Elysian


2021 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Andiamo

Andiamo


2023 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Escapade

Escapade


2023 | Length: 54.00ft

Guests: 8  | Cabins: 5   | Crew: 2


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Windward

Windward


2021 | Length: 55.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Luna Bliss

Luna Bliss


2020 | Length: 47.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Belle Vie

Belle Vie


2020 | Length: 49.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Island Standard Time

Island Standard Time


2021 | Length: 49.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Alora

Alora


2024 | Length: 49.00ft

Guests: 6  | Cabins: 3   | Crew: 2


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Borrowed Bounty

Borrowed Bounty


2024 | Length: 49.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Oceana

Oceana


2021 | Length: 49.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Apricity

Apricity


2023 | Length: 46.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Bella

Bella


2021 | Length: 49.00ft

Guests: 6  | Cabins: 3   | Crew: 2


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Deborah Anne

Deborah Anne


2022 | Length: 49.00ft

Guests: 6  | Cabins: 3   | Crew: 2


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Harmony

Harmony


2022 | Length: 49.00ft

Guests: 8  | Cabins: 4   | Crew: 2


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Siete Mares

Siete Mares


2025 | Length: 78.00ft

Guests: 8  | Cabins: 4   | Crew: 4


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Best Destinations for Caribbean Sailing Holidays

Best Time to Sail the Caribbean

The best time to sail in the Caribbean is from November to June with peak season being December to April. Temperatures stay pretty consistent year-round, averaging 28-32oC with the majority of the rain falling between July and the end of October. Steady trade winds blow at 15-25 knots during the peak months of December to April. The hurricane season runs from June to October.

 

Bareboat vs Crewed Caribbean Yacht Charters

A bareboat yacht charter in the Caribbean is for those who have previous sailing experience and/or a sailing qualification. Skipper your own yacht and decide on the best sailing route for you and your crew. Our Caribbean sailing charters are on top quality monohulls or catamarans ranging in size from from 2 cabins to 6 cabins. Catamaran hire in the Caribbean is very popular as you have the space to easily moor these comfortable boats. On a bareboat charter you can choose to cook onboard or visit the excellent cafes, bars and restaurants to sample the local cuisine.

For those without sailing experience or who are looking to experience the ultimate luxury vacation, a crewed yacht charter in the Caribbean is for you. Imagine island hopping aboard your own private yacht, an experienced crew taking care of the sailing, ensuring you visit all of the top places and undiscovered gems that the area has to offer. Anchoring in a beautiful bay and relaxing onboard with a delicious meal prepared by your personal chef. This is the incredible experience to be had on a crewed yacht charter in the Caribbean.

Crewed yacht charters in the Caribbean are an excellent choice for an unforgettable honeymoon, wedding anniversary or special birthday celebration. They are equally ideal for those looking to relax or enjoy a memorable trip with friends and family. A wonderful vacation for all ages with plenty to keep everyone happy - join in the sailing if you want, or just sit back and relax.

Each yacht has professional crew who are first class sailors and guides to the islands, not to mention congenial and interesting hosts. The local knowledge of your crew is invaluable, enriching your holiday and ensuring you have a personalized and authentic experience. The chefs excel at fine cuisine and your yacht charter includes all meals onboard - a full breakfast, light lunch, hors d’ouevres served with cocktails, and a 3-course dinner.


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The Best of the British Virgin Islands

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