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Monohull yacht sailing holidays & tours in the Caribbean

Monohull yacht sailing holidays & tours in the Caribbean

Discover the magic of sailing holidays in the Caribbean! Monohull: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

  • Sailing Holidays
  • Caribbean
  • Monohull

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 4 reviews
    almost
    confirmed

    7 Days Sailing Cruise around St. Maarten and the BVI's incl. breakfast and lunch on board

    from 28 May - 6 nights
    BVI - British Virgin Islands Caribbean
    1 person interested
    in this holiday
    1.276 1.225€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 28 May - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.537€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 4 June - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.537€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 11 June - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.537€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 18 June - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.537€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 9 July - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.537€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 16 July - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.537€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 23 July - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.559€ Per person
  • 1 review
    almost
    confirmed

    The Paradise on a sailing boat with all inclusive

    from 6 August - 7 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.559€ Per person

Why you should book a holiday with Sailsquare?

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Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Monohull yacht sailing holidays & tours in the Caribbean

97 reviews
18 / 10
Sandra K.

Sandra K.

review about Sailing course in the Grenadines March 2022

8 / 10
I guess the communication was the biggest issue, despite speaking some English relaying information back was poorly executed by the skipper, which have cost me my flight, some lack of empathy during hiking trips instead of allowing time to rest he was pushing for faster or take the bus. Speaking French round the table despite 2 people not speaking the language out of 4 was little rude, otherwise he was very caring when I was unwell during sailing at times and provided effective medical solution, The trip however was a blast, beautiful islands and locals with packed activities, and amazing memories to remember.
Martine G.

Martine G.

review about Sailing course Pogo 12.50 - Heading for Guadeloupe POGO 12.50 January 2021

10 / 10
Perfect agreement between the man, Antoine, and the Pogo, wind, waves, paradisiacal spots, "funny" teammates, precise educational objectives, the whole contributed to the success of 100% of this "open sail" course! I recommend...
Fabian M.

Fabian M.

review about 7 Days Sailing Cruise around St. Maarten and the BVI's incl. breakfast and lunch on board January 2021

10 / 10
First-class sailoring, first-class company, first-class sailing boat, first-class experience. Rob is an exceedingly competent skipper of a superb sailing yacht. On the human level, Rob and Jacky are absolutely delightful people who go out of their way to make you feel welcome and comfortable in every way. Cannot recommend more highly!
Fabian M.

Fabian M.

review about Christmas in the Caribbean ... a dream called the Grenadines December 2019

10 / 10
Michele is an excellent skipper -- technically sound, mature and responsible -- and an excellent host on board. He is also delightful company. I recommend him without qualification
Aleksandra Z.

Aleksandra Z.

review about ALL INCLUSIVE holiday at the Carribeans! (meals and beverage included & flexibles dates!)) February 2020

10 / 10
We had some amazing time with Giulia and Rodrigo in San Blas islands. They are most friendly and professional hosts that one can imagine. Giulias cooking is just great, while Rodrigo provides some fresh fish caught by himself. The boat was very comfortable and tidy. We can definitely recommend holidays with them!
Alex R.

Alex R.

review about Grenadines on a sailing boat with Skipper and Hostess among the pearls of the Caribbean - SUPER LAST MINUTE DISCOUNT January 2020

8 / 10
Sail fast, Live slow! 53 feet boat well updated with new sails and modern equipment without loosing the cachet of a vintage boat with tek-dek, etc. Designed to feel like home, all comforts on board, even TV and AC if it's what you're into and according to your budget. My bed was comfortable. If a couple, I would ask the master bedroom. With real shower and space that I never seen before in a sailing boat. We got an average of 8/9 knots of speed on the first day with picks of 12 knots! Great destinations. Beautiful spots. Clear waters full of fish and turtles. He delivers according whatever you are into and fixes whatever missing on board. Good host, Italian flair, recently reconverted in the Caribbeans, passionated, helpful and basic cooking. Does the best barracuda ceviche! Ask him to saber the Champagne ;) Check prices and what services are incl or not before booking, as with different languages, miscommunications happen. Also about moorings prices w service. Arrivée á bon port!
Giulio M.

Giulio M.

review about Choose your dream destination. December 2019

10 / 10
Pierre is a good experienced skipper that can suggest you the best places to visit, he's also a good cook and will get your vacation very comfortable.
Luca D.

Luca D.

review about week at the San Blas Islands Panama - All inclusive March 2019

10 / 10
ROBERTO SKIPPER: supermitic supersympathetic and helpful, deep connoisseur of the SanBlas makes you feel at ease and manages to make you spend an unforgettable holiday. CREW: very friendly and helpful to support the activities on board. BOAT: large and spacious, very lived, a refitting would be advisable.
Renato M.

Renato M.

review about Guadalupe sailing January 2019

10 / 10
Navigate safely and with reasonable distances. Ideal for quiet and relaxing holidays and fully enjoy the places. Stefano and Monica pamper guests and let them enjoy the boat. Advised
Noëlle G.

Noëlle G.

review about Learning and relaxation in the Grenadines! January 2019

10 / 10
Paradise week in the Grenadines. This sailboat is a very efficient boat that allows you to combine the pleasure of sailing and learning. Hervé takes the time to explain each maneuver and answers all the questions. He is also a good cook! There was a very good understanding between the different teammates, jovial atmosphere on the edge and exceptional anchorages.
Marzia M.

Marzia M.

review about New Year's in the Grenadines December 2018

10 / 10
Hello, I'm Marco, I wanted to thank the skipper Francesco and the skipper Anna for the professionalism, courtesy and kindness of how they welcomed me and the other guests in the 2018 end-of-year cruise. Francesco is an exceptional and experienced sailor, we have always felt safe in any situation. A heartfelt thanks for the wonderful holiday that you made me pass. Hello and good luck
BERNARD T.

BERNARD T.

review about What have you plan for New Year Eve? Get on board and enjoy the Caribbean December 2018

10 / 10
I had a great week on board to start this new year. The combined welcome and hospitality of Anna and Alfonso are very appreciable A week of tranquility to enjoy the life on board animated by Anna, life on the sea and all winds skippered by Alfonso, with the discovery of the terrestrial environment of the islands and their inhabitants. In summary ready to go back on the sailboat Buen vento e ci vediamo presto Bernard il francese
Matteo C.

Matteo C.

review about Last minute - New Year in the Caribbean heat sailing between the Grenadines Islands! December 2018

10 / 10
Renato is a great skipper and a wonderful travel companion. With a few words he knows how to make the right directions to navigate and to spend good time among people on vacation. We discovered together those wonderful places that are the Eastern Caribbean. The wind always blows strongly in those parts in December but we have never taken a step back Thanks again Renato. See you soon Anonymous
Gonzalo B.

Gonzalo B.

review about The best of a sailing cruise in Carabbean with All Inclusive formula, in Guadeloupe island !! November 2018

8 / 10
Francesco it's a dedicated, passionate and experienced skipper. He always tries to fulfill all your expectations, changing the itinerary on the way if it's necessary. His boat is safe and comfortable.
Sergio V.

Sergio V.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Also in this second holiday experience with Fabiano I had the opportunity to appreciate his professionalism, experience and sympathy. I hope to be able to sail by your side again soon! Good wind :-)
Francesca B.

Francesca B.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Wonderful holiday! Amazing places, gorgeous crew and extremely knowledgeable skipper. Thank you
Antonio B.

Antonio B.

review about Come relax under Guadeloupean's coconut trees! April 2018

6 / 10
Didier and Elisabeth have done everything possible to put us at ease and meet our needs so they deserve our. thanks and an overall positive judgment. However, the possibilities to improve their service are really many: Point out that you speak only French. Make sure that the crew members like the presence of animals on board. Find out about the eating habits of your guests and do the shopping with them or by mutual agreement. use receipts to actually make the accounts of galley ports and supplies... It is not a tax but a reimbursement of expenses. Finally, remember that your guests have chosen a holiday on a sailing boat ... to sail!
Fabiano C.

Fabiano C.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Mythical Sergio! Together we sailed the difficult seas of the Bahamas. Thanks to his competence and his charisma we had fun juggling fjords and channels of very complex currents, in total serenity! Thanks Sergio
Fabiano C.

Fabiano C.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Great Goffredo! We sailed together in the aradiso of the Bahamas. Thanks to his help we had an easy life in managing navigation in the difficult waters of the Caribbean. Thanks Goff!!
Fabiano C.

Fabiano C.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Great Luke! Together we sailed in the paradise of the Bahamas and thanks to his expertise we extricated ourselves with great success in the difficult seas of the Caribbean. Also excellent in the management of its crew, boat and activity both in the water and on land. What can I say... A true Commander!
Carla P.

Carla P.

review about The Guadeloupe, paradise on earth! April 2018

10 / 10
Professionalism, extreme kindness, attention to detail and a lot of intelligence: the boat holiday with tranquility and emotions of navigation, snorkelling, relaxation and excellent food. Safe skipper and great cook Thank you
Max C.

Max C.

review about Relax in Guadeloupe, discovery and gastronomy March 2018

10 / 10
Amazing stay with Manu! We immediately felt super comfortable on his boat and everything was ready when we arrived on board. He knows Guadeloupe very well (all the Caribbean in general) and made us discover little corners of paradise. He made homemade bread every day, good dishes, we went fishing lobster, drank delicious ti'punch, snorkeled, kitesurfed and nice walks on land. An ultra rejuvenating week that gives you the impression of having left 1 whole month :) The boat is very comfortable and has a lot of charm: we had the cabin at the back, with a private bathroom. Manu has adapted the program well to our desires according to the wind conditions. Superb sailing throughout the week in 27-degree water! If you want to discover the Caribbean by sailboat, Manu and his freelance boat will be your best travel companions. To start again as soon as possible. Thank you!
Angela B.

Angela B.

review about San Blas Cruise, Panama - All Inclusive February 2018

10 / 10
Andrea and Kikka made us spend a wonderful week at the San Blas, thanks to their exquisite hospitality, the excellent navigation for the great experience of Andrea and the refined cuisine of Kikka.
Agata L.

Agata L.

review about Martinique, Le Grenadines, Tobago cays and return. January to the heat January 2018

10 / 10
Alessandro the ideal skipper for a boat holiday. His professionalism in managing the boat gave me confidence. His decisions have always been considered and discussed by the group. A cheerful funny person and a great cook.. while sailing he caught several fish (tuna, barracuda, etc.) cooking them with the help of a nice hostess Priscilla made our days on the boat pleasant carefree and with scenery of bays and unforgettable beaches. It made each day different from the other. A downside? yes c is .. despite suffering from seasickness and it was my first experience on the boat I will not be able to help but choose another catamaran holiday ... also for those who want to see many islands and dive into many waters from blue to aquamarine blue with beaches from black sand to white meeting sea turtles colorful fish and intense vegetation with inhabitants ready to give you lobsters and fruit .... CARIBBEAN
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