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All inclusive yacht sailing holidays & tours in Caribbean

Discover more than 9 opportunities to get on board a All inclusive adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.

9

experiences

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4.2

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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4.2

Premium

TORTOLA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

BVI - British Virgin Islands

Starting from

€1,760

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

Saint Martin

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+2 travellers

Have booked

Starting from

€1,630

Per person

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4.2

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

€1,795

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

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+2 travellers

Have booked

Starting from

€1,560

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

BVI - British Virgin Islands

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+6 travellers

Have booked

Starting from

€1,525

Per person

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4.2

Premium

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

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

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+2 travellers

Have booked

Starting from

€1,465

Per person

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4.2

Premium

GUADELOUPE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Has booked

Starting from

€1,320

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

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 - All inclusive yacht sailing holidays & tours in Caribbean

26 reviews

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Paradise on a sailing boat with All Inclusive

07/19/2023

Liane F.

-

Brazil

Wonderful week!!!! I recommend for everyone who loves sea, hot temperatures, piece, relax , nature. Mira is fantastic, excellent company, cooks very well, makes you feel comfortable, excellent skyper!!! Congratulations ???????? San blas, is A place to be visit . The best way is to be in sailing boat. Don’t loose it, you will never forget!!!! Thank you Mira for all nice days ????????????????????
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Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook

05/7/2023

Rob H.

Stunning trip - wonderful deserted beaches, incredible snorkling (though sad that the coral is so depleted), and delicious food. Skipper was Eric and Yuna i.c. the kitchen.
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EXUMA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

03/30/2023

Gianluca C.

Esperienze nel complesso ottima ,equipaggio gentile e capace ,skipper espertissimo,livello del cibo e preparazione ottima . Tutto ha funzionato senza intoppi ,per l accoglienza consiglierei hai non esperti di farsi organizzare accompagnamento dall' aeroporto. Stagione non fortunatissima ma nel complesso non male posti molto belli non adatti alla pesca ,mare splendido ,esperienza positiva
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Premium 8 days on Catamarans with hostesses aboard the Grenadines - All Inclusive

09/1/2022

Stefano C.

-

Italy

Viaggio molto bello e ben organizzato. Lo skipper era Claudie, molto preparato, preciso e super affidabile. Karin invece preparava ottimi piatti durante i vari giorni, oltre ad aiutare Claudie. Davvero tutto molto ben organizzato. Catamarano molto bello e ben tenuto. Per chi fosse interessato, Claudie è anche disponibile per domande in merito alla navigazione. I luoghi visitati valgono davvero la pena! Davvero consigliato!

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