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!
What to expect on a Sailing adventure
Sail the Croatian Islands with us!
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!
Ways to sail
Most popular destinations for a sailing holiday
- With picture-perfect ports steeped in history and sandy stretches of stunning coastline, the Mediterranean is one of the world’s best sailing destinations. From island hopping to whitewashed villages in Greece to sailing around Dubrovnik in...See Adventures
- A wealth of laid-back and adventure-filled sailing destinations await in Latin America. Embark on a once-in-a-lifetime holiday around the Galápagos Islands, get intimately acquainted with Cuba, or cruise through the technicolour ports of theSee Adventures
- See the very best of Oceania on a sailing trip to the Lands Down Under. Cruise your way through the Whitsunday Islands in Australia with daily dives in the Great Barrier Reef, or soak up New Zealand's unique Maori culture and stunning scenery at...See Adventures
- Whether it's Thailand, Indonesia, or Vietnam, a sailing vacation in Asia promises fascinating cultural highlights, scrumptious cuisine, and exotic ports of call. From longtail boat rides through Phuket's postcard-perfect reefs to a tropical...See Adventures
Sailing adventures around the world
Africa
See all 47 toursAsia
See all 102 toursAustralia/Oceania
See all 9 toursEurope
See all 347 toursLatin America
See all 119 tours
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!
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!
Best tour companies for Sailing adventures
Much loved by our past travelers, these adventure operators know how to craft the perfect sailing escapes!
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