Where to learn to sail in the Caribbean and the best sailing schools

Apr 21, 2023 BY Paul McWilliams

If you had to pick one world destination to learn the basics of sailing, the Caribbean should be top of your list. It’s an ideal combination of stunningly beautiful islands, sparkling blue water, perfect weather and friendly welcomes. And, perhaps unsurprisingly, the best places to learn to sail in the Caribbean are among the top spots worldwide.

Learn to sail in the Caribbean flickr image by Jason Pratt

Best places in the Caribbean to learn to sail

However, with so much choice comes the difficulty of making a decision. So, to make things a little easier, we’ve picked five of the top destinations for beginner sailing in the Caribbean and the best sailing schools in the region.

Best Caribbean sailing schools and destinations

Our choices are mainly land-based holidays with sailing schools that take you out on the water in small craft for day sessions. However, we couldn’t resist including one option to learn to sail in the Caribbean on a live-aboard.

Best places in the Caribbean to learn to sail Flickr CC image by Cowbell solo9


Situated in the Leeward Islands of the Caribbean, Antigua is a small island that occupies a big place in the world’s imagination. With its deep harbour, it’s a popular cruise ship stop off which means it can get a bit busy with tourists – but it’s easy to see why.

The One Deck Sailing School is a RYA Training Centre offering everything from shore-based theory courses for beginners to professional Boatmaster courses. There are also plenty of practical courses and professional qualifications. All in the heart of the Caribbean on one of its most iconic islands.


Enjoy world-class sailing in Grenada and Petite Martinique, giving you the opportunity to explore the exotic islands and deserted shorelines. Sailing allows you to experience them in a way you never could onshore.

Learn to sail in the Caribbean flickr image by Meg Stewart

The Blue Water Sailing in  Grenada offers a range of courses for those looking to learn the basics, right up to full time cruisers or racers. Their training courses are tailored to each individual sailor and there’s even a two-hour trial course so you can see if sailing is for you.


A beautiful island offering great sailing conditions at one of the Caribbean’s most well-known destinations. . The Barbados Sailing Association runs regular regattas and is the place for experienced sailors to go offering in everything from dinghies to keel yachts.

But for lessons check out Ship Shape Barbados. This year-round sailing school offers comprehensive sailing lessons to groups and individuals of all ages. That could be beginner lessons, race training and even sailing camps for kids.

best Caribbean sailing school pixabay royalty free image from antigua

British Virgin Islands

The island of Tortola on the BVIs may not be the most well-known place in the Caribbean but that’s its charm. This small but exceptionally beautiful island has the clear waters and golden sands you’ll find elsewhere but without the tourist hoards.

Coastal navigation is relatively simple here, but there are enough currents and tides to keep it challenging. Steady trade winds and brisk seasonal winds also mean there’s enough for more advanced sailors too. The Swain Sailing School offers a range of sailing courses for all levels and only uses fully-qualified IYT, RYA and ASA skippers.

The Grenadines

Ok, so land-based sailing schools in the Grenadines are few and far between but we just couldn’t miss this off the list. A chain of 32 islands in the Windwards, as you might expect this is a beautiful and exciting place to learn to sail. Idyllic and untouched islands are surrounded with white sand and tranquil waters.

learn to sail in the Caribbean flickr image by Cowbell Solo

Locals on islands like Mustique, Bequia and Canouan are as laid back and welcoming as you would imagine. The Barefoot Offshore Sailing School, or BOSS for short, offers a range of ASA qualifications on live-aboard sailing excursions around the Grenadines.

Where to learn to sail in the Caribbean?

So, there you have five of the best places to learn sailing in the Caribbean. Of course, there are many others but if you’re looking to learn the basics, take beginner courses or sail the best waters, the above are hard to beat.

We hope you found this guide to the top places in the Caribbean to learn to sail and the best Caribbean sailing schools useful. Often sailing holidays are the best way to learn the ropes. Alternatively find sailing experiences worldwide to get a taste for life under sail.

Antigua And Barbuda, Barbados, British Virgin Islands, Caribbean, Caribbean Sea, Grenada, St Vincent And The Grenadines
Beginner, Exercise, Gym, RYA (Royal Yachting Association), Stretching, training
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