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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.

11

experiences

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4.5

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

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+2 travellers

Have booked

Starting from

€1,150

Per person

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4.5

Premium

BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

Duration:

7 days - 7 nights

Caribbean:

BVI - British Virgin Islands

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+4 travellers

Have booked

Starting from

€1,420

Per person

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4.5

Premium

EXUMA Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Caribbean:

Bahamas

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+16 travellers

Have booked

Starting from

€1,430

Per person

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4.5

Premium

Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

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+4 travellers

Have booked

Starting from

€1,280

Per person

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4.5

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Has booked

Starting from

€1,150

Per person

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4.8

Pogo 12.50 sailing course - Heading south to the Grenadines!

Duration:

9 days - 9 nights

Caribbean:

Grenadines & Martinique

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+5 travellers

Have booked

€1,553

Per person

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4.5

Premium

Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

10 days - 10 nights

Caribbean:

Grenadines & Martinique

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+14 travellers

Have booked

Starting from

€2,055

Per person

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5.0

San Blas: the paradise of the Caribbean

Duration:

6 days - 7 nights

Caribbean:

San Blas Islands - Panama

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+8 travellers

Have booked

€900

Per person

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Tobago Cays Cruise 8 days on a Catamaran full options and recent Bali 4.6

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

Be the first one to book!

€1,802

Per person

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5.0

12 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board

Duration:

10 days - 11 nights

Caribbean:

Saint Martin

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+4 travellers

Have booked

€1,995

Per person

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Breathe, Sail & Flow - Retrait

Duration:

8 days - 8 nights

Caribbean:

Grenadines & Martinique

Be the first one to book!

€3,420

€3,600

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in the Caribbean

167 reviews

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Guadeloupe and its islands in ten days

02/10/2024

Caterina P.

-

Italy

At first, from my son Guglielmo , a special thanks to J.B. for his prompt interest and kind concern when we had problems to get in touch because of my smartphone (next time better an e sim). Than, even if i'm not exactly the best guest to have on bord, i received any kind of support to make me feel confortable and enjoy my stay.. You'll find someone who loves his job and who knows how to do it at best. Really good experience thanks also to Adriana, LuLu e Franco. See you soon!
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Guadeloupe and its islands in ten days

02/9/2024

Franck P.

-

France

J’ai passé un super séjour sur le Mango qui est un voilier de voyage hyper abouti. Des vrais sensations de Voile…..! Merci à Jean Baptiste pour son accueil authentique qui aime partager ces connaissances et qui m a fait les beaux sites traversés…. À très bientôt. Franck
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Guadeloupe and its islands in ten days

02/8/2024

Lucie C.

-

France

Super accueil. Jean Baptiste est très agréable très professionnel et surtout très securisant en.mer. il connaît son bateau dans tous les détails. Très bon séjour avec une bonne ambiance. Jean Baptiste nous a fait decouvrir de très beaux endroits. . nous le recommandons vivement. Adriana Lucie et Franck
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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

02/5/2024

MARIO I.

when I made the reservation I paid for a superior cabin and with the specific request written to you to have a bow cabin. I was assigned a central cabin, I would have liked an official communication from you, informing me of the availability or otherwise of the forward cabin and leaving me the free will to decide whether to accept or not, or withdraw from the contract for which I had paid. commercial and communication incorrectness

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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

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