Sailing is something that everyone should aspire to do at least once in their lives - as Mark Twain declared, "Throw off the bowlines, sail away from the safe harbour... Explore. Dream. Discover." As our sailing vacations travel guide explains, some trips are very hands on, and you'll be acting as a junior crew member, literally learning the ropes. On others, you're free to relax on deck, snorkel and spot wildlife while your skipper takes care of everything.
Where to go for Caribbean
When choosing where to go sailing in the Caribbean, consider your level. There’s challenging blue water sailing to be had on the longer passages between Grenada and St Vincent, and lazy island-hopping in the short channels between the 700-odd islands that make up The Bahamas. The secret of a perfect beginners sailing trip is close together islands: not only do island chains like the BVIs and the Bahamas provide calm waters and short voyages, but there’s also lots to look at: pore over a chart and you’ll see multiple enticing yellow patches signifying good beaches, all only a matter of hours away.
Is Antigua sailing heaven? Hosting world-class events like Antigua Sailing Week, this island is well-trod territory for serious sailors, but there’s plenty of intermediate cruising too. Antigua has its marketing slogan down pat – you’ll hear all about how it has a beach for every day of the year. Being on a sailing boat gives you the best chance of visiting as many of them as possible.
2. The Bahamas
Close enough to Florida to taste the orange juice, the Bahamas, which sit just above the Caribbean, are developed and Americanised. A drawn-out string of flat, coral islands in shallow water, they have supremely easy sailing, so you can spend more time marvelling at the colour of the water (turquoise) and the beaches (white, gold, and even pink on Harbour Island). Head to the northern Abacos, and race nose-to-nose with the rich and famous.
British Virgin Islands
3. British Virgin Islands
The BVIs are a sailor’s playground; a cluster of easily navigable islands that are famous for pirate history. Don’t miss ‘the Baths’, a granite-strewn beach on Virgin Gorda, or legend-rich Norman Island. The BVIs suffered extensive damage in Hurricane Irma in 2017 but are fully open to tourists. There is still some clean-up in progress, but all beaches are open. Visiting now will bring welcome income back to the region.
Larger than you think, and with some of the Caribbean’s most untouched coral reef, Cuba has 5,700km of coastline and needs a little longer to get to know, say, two weeks. Explore the island’s colourful underbelly by trawling the southern coast, between Trinidad and the coral reefs of the western Cayos. Having a crew on board will help you navigate this less-well trodden territory.
Waft along the shores of spice island – though you might need to go on shore to smell the native nutmeg. Grenada offers challenging sailing in blue water between its main island and the six far smaller islands to the north. Sailing bareboat, take courage and make some adventurous crossings from Grenada to Carriacou and up through the Grenadines towards St Vincent.
Our Caribbean sailing Vacations
If you'd like to chat about Caribbean sailing or need help finding a vacation to suit you we're very happy to help.
Caribbean sailing travel advice
Lucy Wade, from our specialist sailing vacation company Sunsail, says:
“The Caribbean is a sailor’s paradise. And with all the hidden beaches only reachable by boat and the chance to island hop between so many little islands, sailing is the best way to see the Caribbean.”
When is the best time to go?“December through to March is the most popular time to go sailing in the Caribbean due to glorious weather and light winds. I would however always recommend customers to travel slightly later around April/May time to avoid the crowds and having those breath-taking beaches all to yourselves!”
Bareboating tips“Remember, on bareboat charters the moorings/berths are not pre-booked unlike the flotillas. This may mean in peak season we will suggest arriving earlier in your chosen destination for the evening to avoid disappointment.”
Sailing qualifications“If you would like to take one of our yachts out without a skipper on board, you would need a sailing license. The minimum license required would be either the RYA day skipper or the ICC.”
Packing essentials“Don’t forget a waterproof camera! The marine life is unforgettable so don’t forget to capture each moment!”
More about Caribbean sailing
What makes for a great sailing vacation? The Caribbean knows the answer: gorgeous weather, steady winds, a cocktail of tropical scenery – plus rum punch, a sailor’s best friend once the anchor’s set. Discover our sailing vacations in the Caribbean.