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.

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We’re offering 15% OFF sunny adventures to Southeast Asia, Central America, the Caribbean and more. Hurry though, offer ends 30 April 2018 and applies to trips departing between 1 May and 31 August 2018.

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Our Caribbean sailing trips

Cuba Sailing Adventure

9 Days From €1,288

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 €1,755

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.

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 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.

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.

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

'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.

FAQs

When’s the best time to visit the Caribbean?

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.

Reviews

Our trips score an average of 4.63 out of 5 based on 60 reviews in the last year.

Cuba Sailing Adventure, March 2018

James Russell

Excellent trip with great staff, beautiful locations you would not otherwise see and the best food you'll eat in Cuba!

Review submitted 19 Apr 2018

Bahamas Sailing Adventure, April 2018

Craig Knott

This was an amazing trip, with an outstanding crew. I learned a few sailing skills, while also getting to sit back, relax and enjoy some rum!

Review submitted 16 Apr 2018

Bahamas Sailing Adventure, March 2018

Ana Boza

The catamaran was absolutely the perfect boat to sail in the Abacos. The island hopping experience is wonderful and blue seas are world class beautiful. Our crew was terrific too. We did not do as much sailing and motoring to reach the destination as provided on the itinerary. The food quality was acceptable but fresh fish would have been nice to see on our trip. Overall, they can twig the experience with more sailing and better quality of food and that would make this trip perfect!!

Review submitted 14 Apr 2018

Cuba Sailing Adventure, March 2018

Claire Long

Very relaxing & wonderful experience, would recommend. However be aware that 7 day’s is quite a long time to be in close proximity with your fellow passengers given the limited space onboard. It’s not the kind of trip which would be recommended for someone who isn’t sociable. 4 day’s onboard the boat would have been sufficient.

Review submitted 12 Apr 2018

Bahamas Sailing Adventure, March 2018

Suzanne Eblen

This was my first solo trip, so I was a little nervous at first....but as it turned out it was the best thing I've ever done, as now it's opened up the world for me. Captain Judy was wonderful, Megan our chef was fantastic, the boat was beautiful, the water was luminescent, the islands were beautiful, and my fellow travelers were all amazing people that I'm very grateful to have met. Could not have been better....I will be signing up for another Intrepid trip!

Review submitted 08 Apr 2018

Cuba Sailing Adventure, March 2018

Amy Ratcliff

If you are considering travelling alone but unsure whether you have the confidence to go, book with Intrepid. The holidays are well thought through, you meet like minded people and you really get to experience a country.

Review submitted 07 Apr 2018

Bahamas Sailing Adventure, March 2018

Chantal Beckmann

I really loved the experience of living aboard a sailboat catamaran in the Bahamas for a week. It is the best way to see the islands i my opinion.

Review submitted 05 Apr 2018

Cuba Sailing Adventure, March 2018

Kathryn Brewster

An amazing week of relaxation but definitely organize some yummy snacks to take in between meal times. The food was amazing and the ability to jump straight into the water is something I’ll miss.

Review submitted 04 Apr 2018

Cuba Sailing Adventure, March 2018

Linda Chigaru

The Cuba Sailing Trip was exactly what it said on the tin. An excellent opportunity to sail around some beautiful Cuban islands, relax, be well fed and meet some new friends. I had a great time and couldn't recommend it more.

Review submitted 03 Apr 2018

Cuba Sailing Adventure, January 2018

Ayesha Wijesinghe

We thoroughly enjoyed our sailing trip in Cuba! Our captain Alberto and our chef Hugo were very friendly and entertaining. Food was great, vibes were great, beaches were stunning, music was great, cocktails were plentiful (and cheap). It was a unique opportunity to visit a beautiful part of Cuba (and cost effective). Great relaxing way to end our time in Cuba. Muchas gracias Alberto y Hugo!

Review submitted 04 Mar 2018

Cuba Sailing Adventure, February 2018

Daniel Mascione

Great unique experience on thats more intimate with max 8 passengers compared to other options. Crew was great and food excellent.

Review submitted 14 Feb 2018

Cuba Sailing Adventure, January 2018

Nicola Hodson

A lovely relaxing tour around the archipelago. Nice catamaran with decent sized cabins and luxury of ensuite loo/shower. A couple of evenings on land but mainly at anchor so pack light and mainly casual, no need for trainers, walking sandals at most. Food fab, lots of extremely fresh fish, lobster, shrimp.....if you need snacks, bring them with you and ideally from home as quite hard to find even in Havana plus the obligatory bottle of rum although they serve a mean cocktail and good price. Reasonable snorkelling but not amazing, suggest bring your own mask as seals not brill but snorkels and fins fine. Depending on month of trip (Jan for me), had some cooler days plus in Havana so bring a warmish fleece/wrap. Overall highly recommended and consider extra days either end to tour Havana.

Review submitted 21 Jan 2018