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

Sailing Tours & Trips

Hoist your 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 getaway in Greece. Whether 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!

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Over 250 Sailing tours with over 4,000 reviews

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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 sailing through the Mediterranean onboard your very own yacht towards hidden gems only accessible by water. 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, local 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

    Discover some of the most unspoiled destinations in the world, 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. Imagine landing your feet on a new beach every day!

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

    Just escape

    Dreaming of a getaway but not really sure of where to go? 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 of the waves whisk you away to that irresistible island paradise you’ve always dreamt of.

Sailing tours of the Croatian Islands

Sail the Croatian Islands with us!

Join an escape to the glimmering Adriatic Coast in the Mediterranean, where you’ll wander through the medieval streets of Dubrovnik, sample local wine in Korčula, and more! With its stunning nature, breezy islands, and glorious seascapes, Croatia sets the stage for a dreamy Adriatic escape of epic proportions.

Croatia is the place for you to sunbathe on striking beaches, dine at the finest of restaurants, and party until the sun comes up (or all of the above!). Covering a mix of fan favorites and less-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 was 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 was super knowledgeable and took us to all the best-hidden restaurants and bars! The yacht was an unbelievable experience, and the layout worked 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 snorkeling 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 furnished 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! Revive your childhood pirate fantasies 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 smooth 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 so many sailing adventures all over the world waiting to be explored, it can be hard to narrow down where to go and what to do. Our Travel Experts can definitely recommend these unique sailing experiences, which are popular with our customers and are guaranteed to give you a ship's log for the books!

  • An elderly, senior couple relaxing on a sailing adventure

    Spoil yourself with a private sail

    If you're up for the splurge, few things can beat having your own vessel to sail the seas on whether it's a romantic getaway, a family celebration or just that bucket list check you deserve.

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

    Dive to discover colorful corals

    Rarely have two travel styles been so well-matched as diving and sailing! Get up close to the reefs, and take a dive into the aquamarine world below before relaxing on deck with a drink.

  • Two felucca boats gliding along the Nile River in Egypt

    Sail the Egyptian way on a felucca

    Witness the Nile unveil its mysteries from your traditional wooden sailing boat. Complete with Middle Eastern cuisine and comfort galore, your journey conjures up the pharaonic past.

Your Sailing trip 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 previous 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 up your onboard 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 cabin, while solo travelers will have to either share a cabin with another passenger of the same gender or pay a single supplement for their own cabin. Most cabins are equipped with ensuite bathrooms, but some vessels may have shared facilities. If you have any doubts, your operator will be able to provide details.

  • How much time is spent off the boat?

    Sailing tours have fine-tuned the balance of on and off-shore experiences. A typical day might be waking up on board, heading for a morning swim, then making port at a historic town where you'll stroll the town together, savor local delicacies, and enjoy free time before returning to your boat for the night. Every sailing itinerary is different but most include excursions at the ports, along with a range of land-based activities.

  • Do I need travel insurance for a Sailing trip?

    Travel insurance is mandatory for most of the adventures on TourRadar and must be purchased before you start your travels. It covers trip cancellations, medical emergencies, lost or stolen baggage, and more. As you can imagine, this is extra important when taking a Sailing trip, and in most cases, you can add travel insurance with Cover Genius directly to your TourRadar booking.

  • How do I book a Sailing adventure on TourRadar?

    Find your next Sailing adventure by perusing our tours by choosing your dates and destination, and use our handy filters such as must-see city or budget, and you'll find the one calling your name. Then you simply 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 travelers, 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.

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