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.
24
experiences
24
experiences
5.0
Duration:
7 days - 7 nights
Caribbean:
San Blas Islands - Panama
Liane F.
Has booked
€1,560
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
BVI - British Virgin Islands
Starting from
€1,760
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Saint Martin
+2 travellers
Have booked
Starting from
€1,630
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Bahamas
+16 travellers
Have booked
Starting from
€1,795
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
+2 travellers
Have booked
Starting from
€1,560
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
Has booked
Starting from
€1,320
Per person
4.2
Premium
Duration:
10 days - 10 nights
Caribbean:
Grenadines & Martinique
+14 travellers
Have booked
Starting from
€2,055
Per person
5.0
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
+38 travellers
Have booked
Starting from
€1,272
Per person
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
Be the first one to book!
€1,802
Per person
4.8
Duration:
11 days - 11 nights
Caribbean:
Antigua and Barbuda
+6 travellers
Have booked
Starting from
€1,790
Per person
4.8
Duration:
6 days - 7 nights
Caribbean:
Guadeloupe
+9 travellers
Have booked
€1,664
Per person
5.0
Duration:
10 days - 11 nights
Caribbean:
Grenadines & Martinique
+3 travellers
Have booked
€2,295
Per person
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Reviews - Yacht sailing holidays & skippered tours in the Caribbean
172 reviews
Paradise on a sailing boat with All Inclusive
07/19/2023
Liane F.
-
Brazil
Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook
05/7/2023
Rob H.
EXUMA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook
03/30/2023
Gianluca C.
7 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board
03/28/2023
Thomas T.
-
Austria
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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.
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.
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.
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.
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.
Across the Caribbean there are numerous sailing holiday itineraries available. Here are some of our favourites:
Caribbean: the most beautiful places to sail
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