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Yacht sailing holidays & skippered tours in the Caribbean

Discover the magic of sailing holidays in the Caribbean! Get on board with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture and gastronomy.

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4.5

Premium

GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

6 days - 7 nights

64 departures available

January - December

Starting from

€1,290

€1,161

Per person - min 2 pax

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4.5

Premium

GRENADINES Paradise - 10 days on a catamaran with hostess FULL BOARD

Caribbean: Grenadines & Martinique

9 days - 10 nights

44 departures available

January - December

Starting from

€1,680

€1,344

Per person - min 2 pax

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4.4

Atlantic crossing by sailboat from Tenerife to the Caribbean

Caribbean: Grenadines & Martinique

20 days - 20 nights

One departure available

November - December

€3,900

Per person

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4.5

Premium

ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Saint Martin

6 days - 7 nights

21 departures available

January - December

Starting from

€1,520

€1,292

Per person - min 2 pax

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4.5

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

53 departures available

January - December

Starting from

€1,270

€1,143

Per person - min 2 pax

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4.5

Premium

BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

50 departures available

January - December

Starting from

€1,815

€1,634

Per person - min 2 pax

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New

Atlantic Crossing by Flotilla from Lanzarote to Martinique

Caribbean: San Blas Islands - Panama

22 days - 22 nights

One departure available

October - November

€4,600

€4,140

Per person

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

11 days - 11 nights

One departure available

March - April

€1,590

€1,352

Per person

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4.4

The British Virgin Islands, an enchanted paradise

Caribbean: BVI - British Virgin Islands

11 days - 11 nights

One departure available

March

€1,490

€1,267

Per person

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5.0

A dream trip for 2 people in the wilderness - All inclusive

Caribbean: San Blas Islands - Panama

6 days - 6 nights

12 departures available

October - December

Starting from

€1,925

€1,733

Per person

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4.5

Premium

BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: BVI - British Virgin Islands

6 days - 7 nights

47 departures available

January - December

Starting from

€1,415

€1,274

Per person - min 2 pax

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Reviews - Yacht sailing holidays & skippered tours in the Caribbean

245 reviews

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GRENADINES Paradise - Week on a catamaran with hostess FULL BOARD

09/7/2026

GURMEET S.

-

US

Sailing around Martinique, St Vincent and the Grenadines, was spectacular, with excursions for a small fee highly memorable. The skipper Gerard was extremely professional, skilled, providing a smooth, flawless sail on a 54 foot, high quality, well equipped catamaran with very comfortable cabins. This experience could easily have been a 5 star rating, were it not for the one crew member dedicated to general guest services and cuisine on board. Dream Yacht Charter employed someone lacking the minimum professional skills one would expect in the hospitality sector. The crew member had an indolent, disinterested and shoddy attitude, leaving guests feeling like a cumbersome burden. Simply asking politely for extra utensils or plates at meal times was met with scowls and complaints about extra washing up! The lack of hygiene on board was also unacceptable with whatever dirt that accumulated over the week inside the cabins and common areas building up. The kitchen was only superficially cleaned and on more than one occasion left flies and insects to fester. Cuisine cooked on board was generally flavourless, uninspired and even insufficient on occasion. This was frustrating when the program is full board for the week. We have travelled on other vessels with other companies and had a far better level of service for similar cost. All that said, we had a wonderful week sailing, we just would not book with this company again.
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ST. BARTH & ST. MARTIN Paradise - Catamaran cruise with hostess FULL BOARD

08/24/2026

Barbara R.

-

IT

5 stars for this trip that fully met expectations, Comfortable boat, prepared and professional crew but at the same time friendly and attentive to everyone's needs. Well thought out itinerary with the right mix of activities and relaxation. The islands are beautiful with beautiful beaches!
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BVI TORTOLA Paradise - Catamaran cruise with hostess FULL BOARD

08/9/2026

Julie H.

-

GB

Living like a millionaire, spending allot less than a resort!!! FABULOUS!!!! Best vacation ever!
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GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

08/5/2026

Maike H.

-

CH

Bernard and Stéfanie were great. The trip was really nice and relaxing, exactly what I had been hoping for.

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Guides & tips


Caribbean

From Cuba to the Grenadines, via the fascinating Bahamas and the green Antilles: Martinique, Dominica and Guadeloupe. Either way, a dream trip to tropical islands.
Guide to the Caribbean by catamaran

When to go in the Caribbean

What are the best times to go to the Caribbean? What climate will I find?
Caribbean weather and climate guide

British Virgin Islands

Crystal-clear waters, rich seabed, lush vegetation and expanses of white sand are the main features of this paradise, which is a must-visit aboard a sailboat!
Guide to the BVI's by catamaran

Grenadines

Une constellation d'îles immergées dans une mer cristalline allant du vert au bleu profond : les fonds marins limpides cachent un trésor qui n'est pas seulement celui des pirates..
Guide to the Grenadines by catamaran

Bahamas

Un voyage en catamaran aux Bahamas est une expérience extraordinaire qui mêle aventure et détente au sein d'un incroyable patrimoine naturel.
Guide to the Bahamas by catamaran

Caribbean: the most beautiful places to sail

Caribbean: departures by month

Other travel ideas

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