header cover

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

cover image
avatar image

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

cover image
avatar image

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

avatar image
avatar image
avatar placeholder

8 travellers

Starting from

€1,188

€1,320

Per person

cover image
avatar image

4.5

Premium

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

Duration:

9 days - 10 nights

Caribbean:

Grenadines & Martinique

avatar image
avatar placeholder
avatar placeholder

16 travellers

Starting from

€1,629

€1,810

Per person - min 2 pax

cover image
avatar image

4.5

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

avatar image
avatar placeholder

2 travellers

Starting from

€1,071

€1,190

Per person

cover image
avatar image

4.5

Premium

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

Duration:

6 days - 7 nights

Caribbean:

Grenadines & Martinique

avatar image
avatar image
avatar image

19 travellers

Starting from

€1,188

€1,320

Per person

cover image
avatar image

4.5

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Guadeloupe

avatar image

Fabian M.

Starting from

€1,071

€1,190

Per person

cover image
avatar image

5.0

12 days of sailing from Martinique to Guadeloupe

Duration:

11 days - 11 nights

Caribbean:

Guadeloupe

avatar placeholder
avatar placeholder

2 travellers

Starting from

€1,680

Per person - min 2 pax

cover image
avatar image

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

cover image
avatar image

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

cover image
avatar image

4.9

Escape to the Paradise on a Crewed Catamaran

Duration:

9 days - 10 nights

Caribbean:

Grenadines & Martinique

avatar placeholder
avatar placeholder
avatar placeholder

5 travellers

€1,650

Per person

cover image
avatar image

5.0

Discover Guadeloupe on a comfortable catamaran - All Inclusive

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

avatar image
avatar image
avatar placeholder

70 travellers

Starting from

€1,350

Per person - min 2 pax

cover image
avatar image

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

208 reviews

avatar image

Discover Guadeloupe on a comfortable catamaran - All Inclusive

12/16/2024

Kamil C.

Great holidays
avatar placeholder

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!
avatar image

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!!!
avatar placeholder

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

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964