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A woman sailing on the calm blue waters of the Cyclades in Greece

Sailing Tours & Trips

Hoist the sails, it's time for an adventure on the high seas! Bring your pirate fantasies to life island-hopping through the Caribbean, or with a dreamy island getaway in Greece. Whether you're setting sail on an exclusive private yacht in the Mediterranean or joining a group trip meandering through the wildlife-rich Galapagos Islands - the world truly is your oyster on a sailing adventure!

A woman sailing on the calm blue waters of the Cyclades in Greece
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What to Expect on a Sailing Adventure

  • A senior couple enjoying their private yacht rental charter together

    A VIP experience

    Feel like a million bucks (literally!) sailing through the Mediterranean onboard your very own yacht. Stop at the hidden gems of the world that are only accessible by boat. Imagine relaxing on the deck at a picturesque island cove, sailing to a private beach with white sands, and plunging into warm ocean waves without another soul in sight. Pure bliss!

  • The famed giant tortoises of the Galapagos Islands in Ecuador

    All-in-one adventure

    Struggling to choose between a cultural experience and an island-hopping getaway? On a sailing tour, you don't have to choose. Good sailing itineraries master the perfect balance of cultural experiences, delicious delicacies, fun activities and even wildlife encounters, like our gentle giants over on the Galápagos Islands.

  • View of a traditional sailing boat cruising around the many inlets and islands of Indonesia

    New day, new destination

    The world truly is your oyster on a sailing holiday! Discover some of the most unspoilt destinations, from Australia's Great Barrier Reef to Africa's Seychelles archipelago. With literally tens of thousands of islands surrounded by remote golden shores, there are very few reasons why you shouldn't go on a sailing adventure.

  • A couple enjoying a romantic moment on the beach in the Maldives

    Just escape.

    Do you dream of just getting away, but are not really sure of where to? A sailing holiday serves as the ideal escape from everyday life with the blue skies and refreshing waters crafting a peaceful home-away-from-home. Let the calm sway, lapping waves and sand between your toes serenade you to create that irresistible island paradise you've always dreamt of.

Sailing tours of the Croatian Islands

Sail the Croatian Islands with us!

Come along with us to the glimmering Adriatic Coast as we wander through the ancient streets of Dubrovnik, sample local wine in Korčula, and more! With its stunning natural setting, breezy islands, and glorious seascapes, Croatia sets the stage for a dreamy Adriatic escape of epic proportions.

Croatia is the type of place where you can sunbathe on striking beaches, eat at the finest of restaurants, or party until the sun comes up (or all of the above!). Covering a mix of fan favourites and lesser-explored locales - from Split to Makarska, Mljet and Hvar - this sailing trip makes for an Adriatic adventure like no other. If you want to see the best of Croatia (while soaking up as much sun as possible along the way) a sailing trip is the way to go!
 
See Croatia Sailing Trips
The stunning coastline of Corfu, GreeceThe stunning coastline of Corfu, Greece

  • Gemma on her Greece Sailing Adventure

    "My first time to Greece and I'm already itching to go back. The whole TruCrew were amazing and I loved every minute! The itinerary works really well and I saw so much of Greece that I wouldn't have ever thought to explore on my own. 10/10 would recommend to anyone looking for a stress-free bucket list experience. The crew were super knowledgeable and took us to all the best hidden restaurants and bars! The yacht was an unbelievable experience and the layout works well for everyone to get to know each other. I've already booked for the Greek Island Hopper next year!"

    Tour: Greece Sailing Adventure by TruTravels

  • Deborah on her Croatia Sailing Adventure

    "The boat was very comfortable, with just 18 of us. The crew were all native Croatians and so delightful and attentive. Because the boat was small, we had daily swims in hidden coves that the big cruise ships can’t go near. Breakfast and lunch were provided daily, and the food was wholesome, tasty, and abundant. The itinerary - Split/Dubrovnik/Split, with overnight stops at different islands each way - was logical, and the tour manager on board gave us an engaging introduction to maritime Dalmatia along the way. The trip was perfect for us!"

    Tour: Sailing Split (Premium) by On the Go Tours

  • Elizabeth on her Galápagos Sailing Adventure

    "I loved it! The G Adventures Galápagos island Hopping trip was awesome. I absolutely loved snorkelling in the crystal clear waters to see a myriad of fish and go through naturally-arched tunnels. Each day was planned perfectly with awesome optional activities. The group size was 14 and not a problem, you also had the option to eat meals with a group or solo but our group leader was organized and made the trip super fun. Highly recommend!"

    Tour: Galápagos Island Hopping (with Quito) by G Adventures

  • Colleen on her Greece Sailing Adventure

    "I  booked my trip with G Adventures at the last minute, so I was a little apprehensive about spending 10 days on a yacht with people that I did not know but this trip ended up being of the best vacations I had ever taken! Our skipper was first class, always making the safety, comfort and well being of his passengers a top priority. The yacht was always spotless, the planning and organization of each day exceptional. There was a large range in age for the group but our skipper took into account each of our expectations and needs which he more than exceeded! I would certainly recommend G Adventures and TourRadar,  I am looking to travel with you again in the very near future."

    Tour: Sailing Greece by G Adventures

Ways to Sail

  • Luxury yacht tours in the Mediterranean

    Yacht

    Modern, comfortable, and equipped with a range of top-notch amenities - including fully-equipped cabins and sun decks - yachts offer an excellent sailing experience no matter your destination. If you’re booking a sailing trip in the Mediterranean, it’s likely you’ll be sailing on a yacht.

  • Traditional gulet cruise in Turkey and Croatia

    Gulet

    Arr me hearties! Bring your pirate fantasies to life onboard this more traditional vessel. Originating in Turkey, gulet boats are wooden sailing boats with two or three masts. Although other countries such as Italy and Croatia use gulets, you’ll find them most commonly on sailing trips in Turkey.

  • Catamaran tours of the Galapagos Islands

    Catamaran

    Designed with ample space, elegant interiors, and high stability, catamarans ensure a safe and comfortable sailing experience. These types of vessels are typical for sailing trips in Asia, and their small size makes them ideal for hopping around islands in the Caribbean and the Galápagos.

Most Popular Destinations for a Sailing Holiday

Sailing Adventures Around the World

Best Sailing Experiences

With many sailing experiences all over the world, it's hard to narrow down where to go and what to do. Our Travel Experts have hand-picked the top sailing experiences you must add to your itinerary.

  • An elderly, senior couple relaxing on a sailing adventure

    Spoil yourself with a private sail

  • Two snorkellers swimming over coral in Australia's Great Barrier Reef

    Dive and discover colourful corals

  • Two felucca boats gliding along the Nile River in Egypt

    Sail the Egyptian way on a felucca

  • A group of friends splashing around in the Aegean waters off the coast of Turkey

    Cool off in the sparkling Aegean waters

  • Aerial view of the beautiful Butter Valley cove off the coast of Turkey

    Go on a treasure hunt to hidden coves

  • Two girls dressed up on a Pirate Party boat cruise

    Celebrate onboard with a Pirate Party

Your Sailing Questions, Answered

  • Do I need to know how to sail?

    On most of our Sailing adventures, you'll have a skipper at the helm or at least some crew members to show you the ropes, so no sailing experience is required. Some private sailing trips allow you to be the captain as you'll have the entire boat to yourself, so be sure to double-check with your operator if that's something you'd like to do.

  • Am I required to help out on the boat?

    Sailing adventure operators are fully equipped with a highly skilled crew, so there’s no need to help out on the boat - unless you want to fine-tune your sailing skills, of course!

  • What are the cabins like?

    This depends on the type of vessel you’ll be on, but it’s likely that your cabin will be small. Typically, couples get their own room, while solo travellers will have to share a cabin or pay a single supplement for their own room. Most cabins are equipped with ensuite bathrooms, but some vessels may have shared facilities.

  • How much time is spent off the boat?

    Sailing adventures have mastered the balance of on and off-shore experiences. A typical day might look like waking up on board, heading for a morning swim, then making port at a historic town where you'll savour local delicacies and enjoy free time before returning back to your boat for the night. Of course, every sailing itinerary is different but most include excursions to various ports, along with a range of land-based activities.

  • Can I combine Adventure Styles?

    Yes absolutely! An adventure is what you make of it, so why not add on wine-tasting in France, a historical tour to multicultural Turkey, or a wild safari ride in Kenya.

  • How do I book a Sailing adventure on TourRadar?

    Find your next Sailing adventure by searching through our tours until you find one that stands out. Simply choose your dates and fill out your details to secure your trip. If you have any questions along the way, our Travel Experts are standing by 24/7!

Current Deals on Sailing Tours & Trips

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Best Tour Companies for Sailing Adventures

Much loved by our past travellers, these adventure operators know how to craft the perfect sailing escapes!

Other Adventure Styles You Might Like

Having a change of heart? Not to worry, we've got plenty of Adventure Styles to suit every taste - from the fussiest connoisseur to the hopeless romantic.

BEACH TRAVEL INSPIRATION HAND-PICKED BY OUR TRAVEL EXPERTS

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