Sailing the Caribbean| Intrepid Travel

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.

Our Caribbean sailing trips

Cuba Sailing Adventure

9 Days From 1288

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

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Bahamas Sailing Adventure

7 Days From 1298

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

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Cuba

Bahamas

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.

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The Abacos

With 290 kilometres (180 miles) of white sand, warm breeze and crystal-clear waters, there’s no shortage of quiet spots to throw down a towel and soak up the sun. Explore sleepy settlements and snorkel for turtles along one of the world’s biggest coral reefs before lying back on the shores of the idyllic Treasure Cay with a Bahaman rum in hand.

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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.

Intrepid's catamarans feature up to four twin-share cabins, three shared bathrooms and two hot showers.

Welcome to your new floating home – a catamaran with up to four twin-share cabins, three shared bathrooms and two hot showers. Each boat comes with plenty of deck space, a communal lounge area and kitchen below decks.

Enjoy home-made meals from your onboard chef.

Steaming bowls of pasta, fresh spicy tacos and a mountain of pancakes for breakfasts, anything is possible with one of our resident expert chefs on board. Bon appetit!

Learn how to sail with your Intrepid sailing skipper.

Learn the tricks to ‘tacking’, ‘reaching’ and ‘coming about’ with your skipper and perhaps try putting your new skills to the test while helping to sail the boat.

Enjoy the sun while relaxing with a good book.

Stretch out on deck and relax with a good book in hand while the winds carry you across wide open waters. Getting hot? Ask your skipper to drop anchor for a refreshing dip.

Explore the history and culture of each destination

Head ashore during the day and discover the history and culture of each destination with your skipper. Every tour gives you plenty of time to get out and explore on your own while also offering optional activities.

Witness incredible sunsets in the Caribbean.

Incredible sunrises and sunsets are all in a day’s work in the Caribbean. Hang out with your new crew while soaking up the sun’s last rays, then stay up late swapping stories over a glass of rum.

Our boats

Orana 44

If sailing through Cuban waters on a trampoline-fitted catamaran sounds like your idea of travel, then hop aboard and grab a cocktail. The Orana 44 is equipped to carry 8 passengers, with 4 double/twin cabins and ensuites, an expansive saloon, and an indoor galley with panoramic views of the islands outside.

Salina 48

Pull up a bean-bag on this twin-hulled luxury catamaran for smooth cruising through the Bahamas, with stacks of room on the sundeck above and saloon below. The Salina 48 comes with a fully-equipped gourmet galley for your on-board chef to whip up some fresh meals for you and seven other potential passengers.

Meet your skipper

'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.