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
7 Days From €1,775
Set sail on amazing sailing expedition to one of the world’s best cruising destinations...
9 Days From €1,840
Set sail across the Caribbean Sea to visit the untouched and idyllic islands of Cuba. A...
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Highlights of the Caribbean
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.
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.
Reviews
Our trips score an average of 4.76 out of 5 based on 46 reviews in the last year.
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, 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
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, 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
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
Bahamas Sailing Adventure, March 2018
Beverley Kellie
I'd recommend this trip, it's a great way to explore The Abaco Islands the whole experience was amazing.
Review submitted 08 May 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
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
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
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
Andrea Schriber
This trip was by far my most relaxing one, it was an experience I will never forget, also because of the good knowledge of Judy who tried always their best to realize a amazing itinerary. Meg‘s cooking skills were amazing and if you are looking for a beach holiday not on the beach, thats what it is, loved it
Review submitted 20 Apr 2018
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
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.
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.
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 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.
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.
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.
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.
Read more about the Caribbean
Aug 06, 2018
How to avoid scams and Havana bad time in Cuba
“Perdón, but where are you going? Can I help?” A voice called out to us from...
Jul 15, 2018
The art of Cuban casa hopping
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Jul 10, 2018
Which style of Latin dance suits you?
When you travel through Cuba, it’s hard not to get swept up in the rhythms of this...
Jun 19, 2018
Our ultimate guide to island hopping in Italy
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Jun 15, 2018
I went to Cuba for the cars and cigars, but it...
I imagined riding in the back of a classic car and salsa dancing in the streets of...
Jun 02, 2018
Yes, we offer Cuba trips for Americans. Here’s...
If you’re an American who thought you’d never be able to get to Cuba, it’s time to...
May 31, 2018
6 essential spots you don’t want to miss in Cuba
From vintage cars to hand-rolled cigars, Cuba is a country with many facets to...
Apr 03, 2018
What to pack for a sailing adventure in Croatia
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Apr 01, 2018
A teen’s eye view of Intrepid family tours
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Mar 19, 2018
“We need very little to be really happy” and...
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Mar 05, 2018
8 things you probably don’t know about sailing...
Cruising around the Adriatic Sea while hopping between islands is one of the best...