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 €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 €1,830

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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Reviews

Our trips score an average of 4.77 out of 5 based on 48 reviews in the last year.

Bahamas Sailing Adventure, July 2018

Emma-Jane Norman

This was an incredible experience, I couldn't have wished to have been taken to more beautiful places to enjoy the world of the sea. Our skipper Judy made this special and I wouldn't hesitiate it recommending it. BEST intrepid trip EVER!

Review submitted 23 Aug 2018

Bahamas Sailing Adventure, July 2018

Christopher Wegener

Bring a small backpack. The cabins are designed for sleeping only. Fill it with these essentials; Swimwear and more swimwear. Flip flops are all the footwear you need. Environmentally friendly sunscreen and soap. Drink lots of water, everyday. Enjoy the shaded places onboard. Help out when you can and get to know everyone. Underwater camera or gopro is a must. Remember to open your hatch when anchored to maximise airflow through your cabin. Close hatches before travelling and before the rain 😂 gets in. Enjoy the experience and be thoughtful of the people and animals you interact with. Take photos, scenery, individual and as a group. Remember cash is king on the islands and is needed for tips at the conclusion of the trip. There is no wifi, embrace this. If you feel sick find a windy, shady place and watch the world go by.

Review submitted 30 Jul 2018

Bahamas Sailing Adventure, July 2018

Nicola McCracken

This tour is an incredible way to experience the Caribbean and all it has to offer. Judy is an amazing skipper and tour leader. Expect to spend plenty of time in the water amongst the sea life. Pack light and be open to having an amazing, fun-filled week with lots of laughs. Be kind and understanding to your fellow tour members as you are sharing a relatively small space.

Review submitted 30 Sep 2018

Bahamas Sailing Adventure, July 2018

Angie Lemmer

Don't be fooled by the notes you have to share a bed with a stranger not might have too........................................

Review submitted 27 Jul 2018

Bahamas Sailing Adventure, July 2018

Judith Domney

Travel through Intrepid takes all the fear away from travelling alone that can sometimes be daunting.

Review submitted 31 Jul 2018

Bahamas Sailing Adventure, June 2018

Rae Wilson

The Bahamas sailing adventure is everything you could hope for and more. Interaction with pigs, turtles and sting rays was incredible. Pure bliss.

Review submitted 18 Jun 2018

Bahamas Sailing Adventure, April 2018

Will Kew

Intrepid is an excellent travel company providing unique experiences around the world with an excellent quality of service. Highly recommended.

Review submitted 02 May 2018

Bahamas Sailing Adventure, April 2018

Fiona Stuckey

If you are considering the idea of sailing, being on a boat, or just want to see the Bahamas - this is the trip for you!! I was overwhelmed by the trip from start to finish. Your guide Judy and cook Meg were wonderful hosts with lots of stories and local knowledge, making sure we had an extra special trip! My highlights were swimming with the pigs, snorkeling, exploring local islands, cruising along on the boat, tasting the local rum punch, feeding turtles and rays, and exploring Green Turtle island on golf carts! Definitely worth the money and travel for this trip of a lifetime! Thanks ladies for such a great adventure! Hopefully I’ll be back next year to see it with you again!

Review submitted 22 Apr 2018

Bahamas Sailing Adventure, April 2018

Carol Harper

The Bahamas trip was wonderful. Do pack light, use sun block, and prepare to relax and enjoy not only the land and sea, but the captain, cook, and fellow passengers, each of whom brings a new angle and loads of fun to the trip.

Review submitted 23 Apr 2018

Cuba Sailing Adventure, April 2018

Jen Dollin

Chasing the April Sun in Cuba. Lobster most days, stunning snorkelling and mojito’s for sundowners. Fabulous captain and crew with 5 passengers who were all there for adventure. Deserted islands, iguanas, hutias, turquoise seas, lighthouses, manta rays, sea turtles, shipwrecks, coral reefs and fish beyond count. Adventure of a lifetime!

Review submitted 05 May 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, April 2018

Joann Bradish

This trip was absolutely amazing... the skipper Judy & cook Megan were excellent at their jobs & so much fun. I fell in love with sailing on this trip. And the Bahamas are stunning, surrounded by beautiful blue/green sea. I like to do activities on holidays, but before this trip I had been working extra hard for a few months, so I also wanted to relax... this trip had the PERFECT mix of both.

Review submitted 31 May 2018

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.