Sailing cruises

Is there a better feeling than clipping through the waves with the sun on your face? Or watching stars come out over the Aegean Sea with a glass of champagne?

Sailing holidays don’t have to be an intimidating tangle of ropes, nautical jargon, and sea monsters – not with Intrepid. Whether you’re a fresh-faced novice or an old salt with callouses on both hands, we’ve got a sailing trip to suit you. Be as involved as you like. Help navigate, tack, and steer; or simply kick back on deck with a copy of Moby Dick and let the world float by. These are small groups on small boats, but with big adventures.

Our sailing cruises

Sailing Adventures, the Intrepid Travel way.

Where you can go sailing

Why choose us

Experienced skippers

Our skippers have years of experience sailing the high seas. There’s no one better to show you the ropes (literally).

Best of both worlds

These sailing vacations aren’t confined to the ocean blue. There’s plenty of time scheduled on land to see the sights and check out the local culture.

Safety first, always

Our yachts are well looked after and regularly maintained and on day one, the captain will also conduct a safety demonstration.

No experience needed

If you'd like to pick up some sailing skills, your skipper can show you how. If not, just relax, kick back on deck and soak up some ocean breezes.

Sustainable travel

We strive to use travel as a force for good. That’s why we choose to give back to the communities we visit, carbon offset all our trips and take our social and environmental responsibilities seriously. We’ve been officially certified as the world’s largest travel B Corp, which means when you choose Intrepid Travel, you can rest assured you’re traveling to improve the planet.

Sailing highlights

Palm tree lined beach in Thailand
Explore the unforgettable islands of Thailand

From the famous landscapes of Phang Nga Bay to the pristine beaches of Koh Phi Phi (and all of the remarkable islands in between), a sailing adventure through southern Thailand promises to produce some of your favorite travel memories ever. Relax on golden sand, take a dip in sparkling turquoise waters, and cast your eyes upon natural wonders you’ve only ever seen photos of. 

A cruise boat in the Galapagos Islands, Ecuador
Island hop your way through the Galapagos

There are some destinations in this world that were made for sailing and the Galapagos Islands is one of them. Whether you want to spend your time spotting the islands’ diverse array of wildlife (think spiky marine iguanas and giant turtles) or simply relax on the boat with a drink in hand as the Pacific Ocean goes by, a boat tour around the Galapagos is sure to be one for the highlight reel. 

Buildings and boats in the harbour at Naples
Get lost in the magic of Italy’s coast

Sailing your way down the Italian coast is guaranteed to be a unique adventure you’ll never forget thanks to a variety of stops featuring pastel villages clinging onto rugged cliffsides, scattered ancient ruins from a lost empire, and tantalizingly blue waters you want to get lost in. From wandering through olive groves to laying out on pebbled beaches, cruise the sparkling Mediterranean at your leisure. 

The island of Mljet in Croatia
Sail the Adriatic Sea around Croatia

On a trip to Europe, Croatia is a must-see but when figuring out how best to explore this Mediterranean country, sailing is the way to go. Whether you want to wander through medieval towns, lose yourself in sparkling blue waters, explore unvisited treasures or indulge in this epic country’s traditional cuisine, you’ll be in utter paradise from the minute to step foot onto your own private yacht – all aboard! 

Our sailing yachts

Yacht on the water in Europe
Europe sailing yachts

When it comes to sailing in Europe, we like to go classic. A single-hulled, 50-foot yacht gives you a taste of traditional Mediterranean sailing, not to mention it looks pretty spiffy in pictures too. A typical Intrepid vessel may come with three twin/double cabins, as well as a couple of single berths. You’ll have a recreation lounge, kitchen, three shared bathrooms and plenty of deck space for lazing around and looking fabulous.

Deck of yacht in Asia
Asia sailing yachts

When it comes to sailing in Asia, catamarans are the way to go. They’re smooth, comfortable, and nimble enough to reach those out-of-the-way cays and little island inlets. The twin hull means there’s plenty of space to stretch out –perfect for those balmy evenings and lazy afternoons. Most of the catamarans in our fleet have four twin/double cabins, three shared bathrooms, a galley (that’s nautical talk for kitchen) and a small living area. There’s even kayaks and paddleboards for those that want to get a little active (and bean bags on deck for those that don’t!)

Reviews

4.8 out of 5 based on 405 reviews submitted.
Reviews are from travellers who have completed their trip and want to share their experience. We show all reviews, but may remove any that include profanity or inappropriate content, are unrelated to the trip or reveal personal details.

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Sail Greece: Santorini to Mykonos

Meaghen · Traveled May 2024
Orestis made the trip. We ended up with a great group, but he was the highlight. He was very knowledgeable of every island we visited and gave us options for what we wanted to eat/see and didn’t mislead us once. He was very safe while also being laid back and fun. He is a kind and wonderful, but also very knowledgeable about sailing and safety. I cannot say enough! 10/10 will book Intrepid again because of the experience he gave us.
Review submitted 25 May 2024

Sail Greece: Santorini to Mykonos

Lauren · Traveled May 2024
This trip was one for the bucket list!! So amazing and filled with wonderful places & people!! Skipper Orestis was the cherry on top!! We would do it all over again in a heartbeat!!
Review submitted 25 May 2024

Sail Italy: Procida to Amalfi

Richard · Traveled May 2024
This is such a great trip, great adventure, great experience, and great memories with some great people.
Review submitted 23 May 2024

Greece Sailing Adventure: Cyclades Islands

Andre · Traveled May 2024
Don’t think twice. Do it. Trip of a lifetime and more than lives up to its expectations. You will fall in love with all the islands!
Review submitted 23 May 2024

Greece Sailing Adventure: Cyclades Islands

Sarah · Traveled May 2024
Trip of a lifetime! 10 days of absolute bliss sailing around the Cyclades. Great group of people, cute little cabin, heavenly swimming stops, beautiful destinations, fantastic skipper.
Review submitted 23 May 2024

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