Why you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
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.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
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 - Sailing holidays in the Caribbean with a local skipper175 reviews
Would you like some support using the platform? We've (almost) always got the answers!
Can't find the perfect holiday for you?
Use our free holiday concierge tool - and let us find your dream sailing experience for you!Let's find it together!
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:
Guadeloupe: the islands with the beautiful waters
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.
Martinique: the island of flowers
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: the islands of Pirates of the Caribbean
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.
Cuba: the largest of the Caribbean islands
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.