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Crewed yacht sailing holidays & tours in Caribbean

Discover more than 14 opportunities to get on board a Crewed adventure in Caribbean. A unique experience with a local skipper, starting at €350 a week.

14

experiences

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4.5

Premium

Abaco Dream - Catamaran Cruise with Chef & Full Board

Duration:

6 days - 7 nights

Caribbean:

Bahamas

Starting from

€1,676

€2,095

Per person - min 2 pax

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4.5

Premium

GRENADINES 11 days on a ALL INCLUSIVE catamaran with hostess/cook

Duration:

9 days - 10 nights

Caribbean:

Grenadines & Martinique

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16 travellers

Starting from

€1,629

€1,810

Per person - min 2 pax

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4.5

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Starting from

€1,071

€1,190

Per person

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4.5

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

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2 travellers

Starting from

€1,071

€1,190

Per person

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4.5

Premium

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

Duration:

6 days - 7 nights

Caribbean:

BVI - British Virgin Islands

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8 travellers

Starting from

€1,188

€1,320

Per person

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4.5

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Grenadines & Martinique

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19 travellers

Starting from

€1,188

€1,320

Per person

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4.8

7 days to the Grenadines North aboard a brand new catamaran

Duration:

6 days - 6 nights

Caribbean:

Grenadines & Martinique

Give this experience a try!

€2,809

Per person

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5.0

Kitesurfing Safari: a unique sporting adventure in the heart of the Caribbean

Duration:

7 days - 7 nights

Caribbean:

Venezuela

Starting from

€3,800

Per person

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5.0

Explore Los Roques by Catamaran - Sailing in the Heart of the Caribbean

Duration:

7 days - 7 nights

Caribbean:

Venezuela

Starting from

€1,950

Per person

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4.9

Escape to the Paradise on a Crewed Catamaran

Duration:

9 days - 10 nights

Caribbean:

Grenadines & Martinique

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5 travellers

€1,650

Per person

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4.5

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Bahamas

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18 travellers

Starting from

€1,545

Per person

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4.8

7 days to the South Grenadines aboard a brand new catamaran

Duration:

6 days - 6 nights

Caribbean:

Grenadines & Martinique

Give this experience a try!

€2,809

Per person

Why book a holiday with Sailsquare?

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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 - Crewed yacht sailing holidays & tours in Caribbean

52 reviews

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

10/20/2024

Daniela H.

-

Switzerland

Dank Nebensaison ein sehr kleine Gruppe von Passagieren. Eine der besten Wochen meines Lebens! Danke an den Skipper (Lucius) und an die Köchin (Sabrina) von Dreamyacht. Hätte mir keine bessere Route oder Crew wünschen können. Einfache Buchung via Saulsquare. Boot nicht mehr neu, Zustand und Sauberkeit aber gut!
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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

10/5/2024

ISabelle T.

-

Canada

Grâce aLucius et à Sabrina nous avons adoré ce voyage, mille merci, tout était parfait... très attentionné et les paysages sublimes nous ont séduit!!!
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EXUMA Dream Premium - 8 days in Catamaran ALL INCLUSIVE with hostess/cook

08/11/2024

Luca C.

-

Italy

Ottima barca ed equipaggio molto competente… peccato per le molte ore di navigazione… mi sarebbe piaciuto fare un po’ più di snorkeling
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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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