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!
Over 250 Sailing Tours With 3,561 Reviews
- -25% off
Sailing Greece - Mykonos to Santorini8 days • (17)"I'm not certain what is meant about transportation, there was no transfer from the ..."From $1,599 $1,199
4-day Split to Dubrovnik One-way Cruise - A-Category above-deck, 18-39s4 days • (9)"Fantastic trip! All of the tour staff were very friendly and helpful. Boat was clean ..."From $444
- -35% off
Sailing Croatia - Split to Dubrovnik8 days • (17)"I enjoyed an excellent trip with a big itinerary and many activities to choose from. ..."From $1,799 $1,169
Dalmatian Voyager - Split to Split8 days • (463)"Everyone else has said it. Chris has got this down to a fine art. His passion for ..."From $1,054
- -40% off
Croatia Sailing Adventure8 days • (37)"Ivan was an excellent guide. He was involved enough that I always felt I had something ..."From $1,535 $921
What to Expect on a Sailing Adventure
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!
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.
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.
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.
Ways to Sail
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.
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.
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
- With picture-perfect ports steeped in history and sandy stretches of stunning coastline, the Mediterranean is one of the best sailing destinations in the world. Explore our holiday packages and start planning your perfect island-hopping vacations...
- 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 the
Sailing Adventures Around the World
AfricaSee all 23 tours
AsiaSee all 43 tours
Australia/OceaniaSee all 17 tours
EuropeSee all 282 tours
Latin AmericaSee all 40 tours
North AmericaSee all 5 tours
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.
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.
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
- -50% off
Abu Simbel with 4 Day - 3 Night In Stander 4* Superior Or Stander 5* Nile Cruise From Aswan & Luxor4 daysFrom $386 $193
Aegean Discovery9 daysFrom $7,165
Gems of the Arabian Peninsula (Start Doha, End Dubai)8 daysFrom $4,095
Gems of the Arabian Peninsula (Start Dubai, End Doha)8 daysFrom $4,195
- -45% off
Sail Dubrovnik to Split-Above Deck8 days • (22)From $1,399 $769
- -45% off
Sail Split to Dubrovnik Above Deck8 days • (12)From $1,399 $769
- -40% off
Egypt Explorer - Felucca cruise & Red Sea10 days • (356)From $994 $596
- -40% off
Croatia Sailing Adventure8 days • (37)From $1,535 $921
- -40% off
Greece Sailing Adventure8 days • (15)From $2,095 $1,257
- -36% off
Croatia Sailing - 8 Days8 days • (5)From $1,495 $955
Best Tour Companies for Sailing Adventures
Much loved by our past travellers, these adventure operators know how to craft the perfect sailing escapes!