Typically the haunt of America’s rich and famous, sailing in 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.

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Our Caribbean sailing trips

9 Days From $1,928

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

7 Days From $2,595

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

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Highlights of the Caribbean

Discover the white sandy beaches and pristine waters of Cuba's Canarreos Archipelago.

Discover Cuba’s hidden archipelago

While not as well-known as its Caribbean neighbours, Cuba’s Canarreos Archipelago is home to stunning fine white sand beaches and turquoise waters filled with marine life. Very limited access to phone and internet means you can spend your day tracking iguanas on deserted islands, lounging on deck chairs (mojito in hand, of course) and tucking into freshly caught lobster dinner as the sun dips on the horizon. 

Explore on the Cuba Sailing Adventure

Pop on a snorkel and explore 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 offshort 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

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

Life on the boat

Curious to see what life in the Caribbean is really like? Here’s what to expect onboard an Intrepid sailing tour.  

Meet your skipper

'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.'  – Dean, British Virgin Islands

Meet your Intrepid skipper, Dean.

'Since my first visit over 30 years ago I’ve had a fascination and love affair with the Bahamas…everything from the gin clear water to the friendliness of the native people, the sea life, history, the loyal “pot cake” island dogs, the uncrowded unspoiled anchorages….and did I mention turquoise is my favourite colour?'  – Judy, Bahamas

Read more about Judy in our interview here


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.


Our trips score an average of 4.6 out of 5 based on 48 reviews in the last year.

Cuba Sailing Adventure, December 2017

Ashley Pow

Cuba Sailing Adventure, December 2017

Poppy Ross

Cuba Sailing Adventure, November 2017

Aurelie Couet

Cuba Sailing Adventure, November 2017

Sarah Keane

Cuba Sailing Adventure, November 2017

Simon Beard

Cuba Sailing Adventure, November 2017

Gary Rolston

Cuba Sailing Adventure, November 2017

Paulette Baker

Bahamas Sailing Adventure, May 2017

Sam Malhotra

Bahamas Sailing Adventure, July 2017

Kathleen Cleversley

Bahamas Sailing Adventure, July 2017

Emily Legault

Bahamas Sailing Adventure, June 2017

Susanne Metzger

Bahamas Sailing Adventure, June 2017

Joel Sonderegger

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