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Yacht sailing holidays & skippered tours in Caribbean

Discover more than 18 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

18

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

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

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

Duration:

6 days - 7 nights

Caribbean:

Grenadines & Martinique

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9 travellers

Starting from

€1,188

€1,320

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

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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5.0

12 days of sailing from Martinique to Guadeloupe

Duration:

11 days - 11 nights

Caribbean:

Guadeloupe

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2 travellers

Starting from

€1,680

Per person - min 2 pax

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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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Sailing adventure through the Caribbean: St Vincent & the Grenadines

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

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4 travellers

€820

Per person

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5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

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66 travellers

Starting from

€1,378

Per person - min 2 pax

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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

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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

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 Caribbean

207 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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Sail with us in the heart of the Paradise called the Grenadines

04/30/2024

Paolo G.

-

Italy

Grazie Luca per questa esperienza indimenticabile! Essere a bordo di Ikigai ci ha fatto capire la vostra filosofia di viaggio e di vita, un'avventura unica che ci ha fatto sentire fra amici e non semplici ospiti o turisti..i posti visti sono incredibili ma il mood respirato a bordo, le attività e il cibo preparato da voi rimarranno scolpiti nella memoria...speriamo di rivederevi e tornare presto a bordo...buon vento!

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