Typically the haunt of America’s rich and famous, ‘sailing the Caribbean’ is now officially open to all.

There’s a reason this equatorial paradise draws so many people each year in search of some R&R. Nowhere else will you find that unique blend of sultry Latin culture, postcard-worthy beaches, colonial history, world-class diving and lip-smacking Caribbean food. And what better way to explore the island chains and tiny archipelagos than your own private catamaran? Book a sun-soaked sailing Caribbean vacation today, then thank us tomorrow when your friends go green with envy.

Our sailing trips in the Caribbean

8 Days From $2,763

Explore the Caribbean on a British Virgin Islands sailing adventure. Sail, snorkel,...

9 Days From $3,110

Set sail across the Caribbean Sea to visit the untouched and idyllic islands of Cuba. A...

7 Days From $1,683

Set sail on amazing sailing expedition to one of the world’s best cruising destinations...

7 Days From $1,594

Visit Dry Tortugas National Park and the uninhabited Marquesas Islands on this unique...

Our Caribbean destinations

Highlights of the Caribbean

Dead Man’s Bay

Drop anchor at Dead Man’s Bay

It sounds like something from Pirates of the Caribbean, but Dead Man’s Bay is the real deal. When the British Virgin Islands need a beach for their postcards, they usually turn to Dead Man’s Bay. Park your yacht just offshore and spend the day chilling on chalk white sands or paddling in the warm shallow waters. No pirates guaranteed.

Explore on the British Virgin Islands Sailing Adventure

Boulevards of Cienfuegos

Wander the boulevards of Cienfuegos

If Cuba has a Paris, this is it. Dock your yacht at the glitzy quay and go for a stroll in the town known as Perla del Sur (‘the Pearl of the South’). Walk down the elegant Paseo del Prado and check out a few early 20th century palaces on the Punta Gorda. Finish the night with a rum cocktail and the sultry sound of Samba. Bliss.

Explore on the Cuba Sailing Adventure

Take a dip at The Baths

Take a dip at The Baths

Take a few volcanic leftovers, leave them to cool for about 70 million years, then flood the area with warm blue waters and you have something similar to The Baths – British Virgin Island’s most photogenic spot. Park your yacht close to the massive boulders, go for a snorkel, then hike through the ‘Caves’ to the white sands of Devil’s Bay.

Explore on the British Virgin Islands Sailing Adventure

Discover the history of Fort Jefferson in the Dry Tortugas.

Explore the ramparts of Fort Jefferson

Fort Jefferson certainly has a long and colourful history – serving as a lighthouse, military outpost, prison and a national park since it was first built in 1847. You can set out on a self-guided tour of the fort and learn about the heroes and villains who have stayed here, visit the moat and spot alligators, or simply sit atop the ruined battlements and watch as sea planes come and go. 

Explore on the Key West & Dry Tortugas Sailing Adventure

Life on the boat

Your home for the duration of your trip sailing the Caribbean will be a catamaran with up to four twin-share cabins, three shared bathrooms and two hot showers. Each boat comes with plenty of deck space for soaking up that Caribbean sun, and a communal lounge area and kitchen below decks. Most meals are included on our Central America sailing trips, prepared on-board by our resident expert chefs.

As always, how much you’d like to participate in the sailing side of things is up to you. Try your hand at ‘tacking’, ‘reaching’ and ‘coming about’, or relax and let the trade winds carry you through the archipelago. Please keep in mind: cabin arrangements can be quite cosy so as to leave more room for on-board communal areas.

Best time to travel

If you’re looking for sunny weather and smooth sailing (and who isn’t?) the best time to head to the Caribbean is December through to April. With more sunny days on average than any other time of the year, you’re increasing your chances of a rain-free trip. It’s worth remembering that topography of each island plays a part too: mountainous islands will attract more cloud cover, while chances of clear skies increase around the smaller archipelagos.
weather caribbean

Skipper profile

'I’ve sailed since I was a child. I was lucky enough to professionally skipper my first yacht at 21 from the UK to Southern Spain, though I’m sure I was skippering rubber rowing boats long before that! For me, it’s the fresh air and sense of self-dependence that draws me to sailing. I’ve always felt closer to the real world on water than I ever have on land. It just makes sense somehow. The best sailing adventures? These happen when you make the most of it! Just breathe deeply, feel the beauty of the world around you and take the chance to explore new places.'

Dean Taylor, British Virgin Islands



Our trips score an average of 4.55 out of 5 based on 29 reviews in the last year.

Bahamas Sailing Adventure, May 2017

Janet Chenoweth

Bahamas Sailing Adventure, May 2017

Roger Halligan

Bahamas Sailing Adventure, May 2017

Angela Person

Key West & Dry Tortugas Sailing Adventure, April 2017

jimmy powell

Key West & Dry Tortugas Sailing Adventure, April 2017

Elise Kidd

Key West & Dry Tortugas Sailing Adventure, April 2017

David Scarratt

Key West & Dry Tortugas Sailing Adventure, April 2017

Jo Stern

Key West & Dry Tortugas Sailing Adventure, April 2017

Barb Mory

Key West & Dry Tortugas Sailing Adventure, April 2017

Joy Harris

Key West & Dry Tortugas Sailing Adventure, April 2017

Alison Merlo

Key West & Dry Tortugas Sailing Adventure, April 2017

Leslie DempseyMarchese

Key West & Dry Tortugas Sailing Adventure, April 2017

Bridget Erlec

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