Yacht sailing holidays & skippered tours in the Caribbean
Discover the magic of sailing holidays in the Caribbean! Get on
board with a local skipper and live a unique adventure with your
crew: learn to sail, explore incredible places, recharge your
batteries and experience the local culture and gastronomy.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your 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 - Yacht sailing holidays & skippered tours in the Caribbean
Crossing the Atlantic was a dream i had for a long time and Dominikus and Patricia made this dream come true in the best way ! Dominikus is a skipper you always feel safe with, he is also a captain who likes to share how things work on the boat and about the wind, sailing and the ocean. And more than this he always put good energy and fun in the crew ! Regarding Patricia, she also is the best. Very attentive of what you may need or how you feel, she cooked everyday (21days) some amazing fresh food, she takes very good care of the boat and make this trip a Luxury adventure ! If anyone dream of crossing the Atlantic or just want to spend time on spanish islands i recommand you join the Genia crew!!
I couldn't have fallen better in the first cruise experience in the West Indies!
It was a fantastic stay in every way.
Jean Baptiste, a truly outstanding skipper who knows how to adapt to all situations. Safety, friendliness, and discoveries. magical sites. He made me benefit from his years of sailing on the Caribbean aboard his sailboat on and very comfortable in. An authentic human experience to renew without moderation!
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...
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!
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
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!
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!
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.
What can I say? Another round another gift: to spend a fantastic week with Filo. For three years now I have been lucky enough to sail among the most beautiful seas that this world gives us, and the company, charisma, sympathy and competence of wire can only make everything extremely perfect!
I left alone and not being a dragon in English I could have had some difficulties. Instead the availability, the sympathy and the professionalism of the crew immediately put me at ease. Holiday higher than expectations, both for the services offered, both for the boat equipped with every comfort, both for the staff and for the itinerary carried out. To be repeated!
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
Eric is a skipper attentive to everyone's needs and knows how to put his human knowledge and the sea at the service of the people he welcomes on his boat.
I am delighted with this cruise on the Guadeloupean islands.
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.
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
Vittorio is an excellent sailor, an excellent cook and his boat is very large, very clean spacious and comfortable. However, communication is not his forte and we learned this the hard way. We would indeed have worked out qq details before departure because we were very surprised to learn that I refused to do any night navigation. And this even for the longest crossings such as the one that consists of going around Guadeloupe or the one between Guadeloupe and Antigua. Balance we barely did half of the planned route: only Antigua and Barbuda while had to go to St Kitts then Nevis and Montserrat (over 10 days it was supposed to be feasible. This change of program led to a rather bad atmosphere within the group of customers who were all the more disappointed that on board there was not only another crew member and among the customers there were also people to ensure the 1/4 night !...
Sailing with Giammy at the helm is a guarantee! Attention and engineering precision combined with a dose of sympathy and good humor! A perfect combination!
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
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
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.
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 :-)
6 reasons to choose the Caribbean for your next sailing holiday:
Warm winter under the tropical sun
Enjoy excellent sailing conditions to learn or improve
Relax in the beautiful coves where you can admire beautiful marine wildlife
Learn about Creole culture and discover a rich architectural and cultural heritage
Delight your taste buds with Creole flavours
Adapt your itinerary with your skipper, and experience numerous islands
The best destinations to visit during your sailing holidays in the Caribbean:
The Caribbean is a popular destination for sailing thanks to a warm year-round climate, stunning scenery, and dreamlike natural wonders. A sailing holiday is an ideal opportunity to discover the Caribbean Islands. Here are some of the most beautiful destinations to be discovered:
This extraordinary concentration of islands is a region rich in culinary tradition, colours and scents. The landscape is varied, with a dense tropical forest and lush vegetation, due to the very fertile volcanic soil. And then there are the beaches of white sand, met by a turquoise sea and coral reef. Between the wild Petite Terre, mythical Marie Galante and striking île des Saintes, there is much exploration to be done under the tropical sun.
The volcanic coast combines lush vegetation and turquoise lagoons dotted with small coves lined surrounded by palm trees. The southern part of Martinique is postcard picturesque, ideal for travellers looking for white sand beaches, coconuts, and warm waters. Martinique has a rich cultural heritage, expressed by its different forms of craftsmanship and delicious cuisine.
Saint Vincent and the Grenadines are located in the southern part of the Caribbean. Aboard a sailboat or catamaran, you have the opportunity to explore a number of the 32 uninhabited, and over 600 uninhabited islands and islets of the archipelago. A true paradise made of fine white sand and turquoise water.
A well preserved, wild archipelago where you can experience extraordinary catamaran sailing holidays. From the cultural and historic journey of the main islands, to the natural splendour of the 50 small islands, each anchorage having its own magic charm. Kick back in beautiful bays, on white sand beaches, snorkel with tropical fish, and explore the marinas and villages ashore as you go.
Enjoy the beautiful marine wildlife whilst sailing Cienfuegos the islands of Cayo Guano, Cayo Largo, Cayo Cantiles, just to name a few. Discover the untouched islands of paradise, swim in crystal clear waters, snorkel over beautiful reefs and spend days enjoying the relaxed atmosphere of irresistible Cuba. Find out why this vibrant country is an unmissable destination for sailing.
All you need to know about your next cruise in the Caribbean aboard a sailboat
The best time to go on a sailing holiday in the Caribbean
Sailing holidays in the Caribbean are best from November to April, during the European winter. This offers the opportunity to escape the colder part of the year, and to instead exchange it for a tropical sun and life aboard a sailboat. The season lasts until June, and then between July and September there are very few options as there is a significant risk of cyclones. However, areas such as the Grenadines are possible to visit during the European summer, as this part of the Antilles is not affected by these climatic events.
How much does it cost for a Caribbean?
It can be more accessible to board a sailboat or catamaran sailing adventure in the West Indies than you might think, for budgets of all inclusive experiences beginning from around €1,200 per person. This budget of such a holiday can be broken down into 3 parts: the plane ticket, the catamaran or sailboat, and the float cash (food, fuel, marina costs, etc). It is possible to find round trip plane tickets to Guadeloupe, Saint-Vincent or Martinique from €400 with a number of low-cost airlines The price of your Caribbean cruise will depend on the period, the services onboard (with or without cook and hostess), and whether it is a sailboat or catamaran. A catamaran sailing holiday in the Caribbean can be significantly more expensive than a sailboat trip given the higher level of comfort. You can find spots onboard catamaran holidays from €600 on Sailsquare and all-inclusive holidays from €1,000.
Transport options in the Caribbean
The Caribbean is home to many airports and there are a large number of different airlines, of different price brackets, connecting the Caribbean with the world. Transport pricing can vary depending on the seasons, with some peak in price around the Christmas holiday period. Transport to and from the Caribbean may be significantly cheaper during the months of November and January.
To travel the Caribbean on catamaran or sailboat - with or without skipper?
A Caribbean sailing holiday experience is a great opportunity to have quality time with family and friends. Do you already have your travelling group formed? No problem! There are a number of whole boat booking holiday listings that allow you to reserve the entire boat.
The best sailing holiday itineraries for your next adventure in the Caribbean with a skipper:
Across the Caribbean there are numerous sailing holiday itineraries available. Here are some of our favourites:
Guadeloupe:: even one week allows enough time to fully enjoy this sublime archipelago. From Pointe-à-Pitre, you make a first stop at Marie Galante, before discovering Les Saintes. Moments of pure relaxation and discovery. If you wish, you can also discover the aquatic fauna and flora of the Cousteau Reserve Marine Park.
Martinique, Saint Lucia & Saint Vincent:: a very beautiful adventure, comfortably doable in one week from Fort-de-France. At first you head for the volcanic island of Saint Lucia, then the lush island of St. Vincent, part of the Grenadines. So many wonderful places await you during this special holiday itinerary.
The BVI:: cross the British Virgin Islands, starting and ending in St. Martin. Your first stop will be Virgin Gorda, where the famous baths await you, before you pass onto Horse Shoe Reef, the Norman Island Caves, and a number of other natural wonders.
Guadeloupe, Antigua & Barbuda:: around 12 days sailing from Pointe-à-Pitre in Guadeloupe. You round the island from the west before going back to Antigua, then continue on to Barbuda and going on down to Pointe-à-Pitre, passing east of Antigua.
Cuba:: departing from Cienfuegos, you can take a week to sail the crystal clear waters surrounding Cayo Guano, Cayo Rosario, and Punta del Este.
Guadeloupe, Antigua & Barbuda:: a week-long holiday from Marsh Harbor. To the east of the island you can discover the neighbouring islands, colourful architecture of Elbow Cay, seven-mile beach of Great Guana Cay, passing by the famous sands of Treasure Cay, and deep bays Green Turtle Cay.
