header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Caribbean

Discover more than 6 sailing holidays in Caribbean. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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

219 reviews

avatar image

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

06/30/2025

Beatrice S.

-

Spain

No se podía esperar más de un viaje. El catamarán grande y nuevo. A/C siempre que hacía falta y agua en abundancia. El Capitán Lutius no podía ser más profesional y simpático. Nos hizo sentir a todos cómodos y siempre proponiendo hacer diferentes actividades en un ambiente divertido y desenfadado. Karin, la chef igualmente agradable y divertida. Muy profesional y atenta a nuestras necesidades. Los lugares que visitamos de ensueño y a pesar de algunas lluvias en línea general ha merecido la pena navegar fuera de temporada al estar prácticamente solos en los sitios más alucinantes. Siempre hemos tenido suerte con el resto de los clientes y en este caso no ha sido diferente y a pesar de ser mayoritariamente de habla francesa nos hemos comunicado muy bien en inglés.
avatar placeholder

12 day Cruising/Sailing Experience around St. Martin and St. Barth's

04/17/2025

Basiel B.

-

United States

We had a fantastic trip sailing around St. Martin, St. Barth and St. Kitts & Nevis with Rob and Jackie, who were super relaxed and made us feel 200% welcome. The boat is beautiful and very well taken care of, a perfect intro to real-deal sailing. Rob is an excellent skipper mindful of safety (& comfort), and Jackie spoils you with her cooking. Snorkeling gear an paddle board available for aquatic leisure. Cannot recommend them more for a relaxing trip around the Caribbean!
avatar image

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

04/12/2025

Carla P.

-

Italy

ottimo skipper e ottimo servizio di bordo con eccellente cibo
avatar placeholder

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

03/18/2025

Patricia A. Mcmahon s.

Wonderful trip. I just wish we saw more of the islands we snorkel by.

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

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964