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Sailing Tours
Sailing Tours
Raise your sails—it’s time for an unforgettable adventure on the open sea! Live out your pirate dreams island-hopping across the Caribbean or enjoy a dreamy escape in Greece.
Whether you’re cruising aboard a private yacht in the Mediterranean or joining a group expedition through the wildlife-filled Galapagos Islands, a sailing adventure offers endless possibilities—the world is truly your oyster!
Over 250 Sailing tours with over 4,000 reviews
All Included Halong Bay 2 Days 1 Night On 3-Star Cruise
From $134
Greece Sailing Adventure: Cyclades Islands
From $2,502
Dalmatian Highlights Split & Dubrovnik Region Cruise
From $1,568
All Included Lan Ha Bay 5- star Cruise - 2 Days 1 Night
From $224
Hanoi - Halong Bay - Lan Ha Bay 2 days 1 night on Cruise
From $198
What to expect on a Sailing adventure
A VIP experience
Experience the luxury of sailing the Mediterranean on your own private yacht, discovering hidden gems accessible only by sea. Picture yourself unwinding on the deck of a secluded island cove, cruising to a private white-sand beach, and diving into warm ocean waters with no one else around—pure bliss!
All-in-one adventure
Torn between a cultural adventure and an island-hopping escape? With a sailing tour, you don’t have to pick. The best itineraries blend rich cultural experiences, local flavors, exciting activities, and even wildlife encounters—like meeting the gentle giants of the Galápagos Islands.
New day, new destination
Explore some of the world’s most pristine destinations, from Australia’s Great Barrier Reef to the Seychelles archipelago in Africa. With tens of thousands of islands framed by untouched golden beaches, there’s no better reason to embark on a sailing adventure. Just imagine stepping onto a new beach every single day!
Just escape
Dreaming of a getaway but unsure where to go? A sailing holiday is the perfect escape from everyday life, where blue skies and refreshing waters create a tranquil home away from home. Let the gentle rhythm of the waves carry you to the island paradise you’ve always imagined.
Sail the Croatian Islands with us!
Escape to the sparkling Adriatic Coast in the Mediterranean, where you’ll stroll through Dubrovnik’s medieval streets, savor local wines in Korčula, and much more! With its breathtaking nature, breezy islands, and stunning seascapes, Croatia offers the perfect backdrop for an unforgettable Adriatic getaway.
Whether you want to relax on beautiful beaches, dine at top-notch restaurants, or dance the night away—or all three—Croatia has it all. This sailing adventure covers a mix of popular hotspots and hidden gems, from Split and Makarska to Mljet and Hvar. If you want to experience the best of Croatia while soaking up plenty of sunshine, a sailing trip is the ultimate choice!
Elizabeth on her Galápagos Sailing adventure
"I loved every moment of the G Adventures Galápagos Island Hopping trip! Snorkeling in the crystal-clear waters, exploring vibrant fish and natural underwater tunnels was incredible. Each day was perfectly planned with great optional activities. The group size of 14 was ideal—whether dining together or on your own—and our group leader kept things organized and fun throughout. Highly recommend this adventure!"
Most popular destinations for a sailing holiday
Mediterranean
With its picturesque historic ports and beautiful sandy coastlines, the Mediterranean ranks among the world’s top sailing destinations. Whether you’re island hopping through Greece’s charming whitewashed villages or sailing along the stunning shores of Dubrovnik, this region offers unforgettable experiences at every turn.
Oceania
Discover the highlights of Oceania on a sailing adventure through the Lands Down Under. Sail around Australia’s Whitsunday Islands, diving daily into the vibrant Great Barrier Reef, or immerse yourself in New Zealand’s rich Maori culture and breathtaking landscapes at...
Latin America
Our Caribbean sailing routes truly stand out between Guadeloupe and Sint Maarten, offering the perfect blend of UNESCO-listed Saintes Bay and Anguilla’s renowned culinary delights. Another fantastic itinerary takes you through St. Lucia and St. Vincent, where you can anchor and explore...
Asia
Whether you choose Thailand, Indonesia, or Vietnam, a sailing vacation in Asia offers captivating cultural experiences, delicious cuisine, and exotic destinations. From longtail boat rides exploring Phuket’s stunning reefs to tropical escapes filled with vibrant local life, your journey will be unforgettable.
Best sailing experiences
With countless sailing adventures around the globe waiting to be discovered, choosing the perfect one can be overwhelming. Our Travel Experts are here to guide you toward unique sailing experiences that our customers love—ensuring your journey will be one for the ship’s log!
Spoil yourself with a private sail
If you’re ready to indulge, few experiences compare to having your own private vessel to sail the seas—whether it’s a romantic escape, a family celebration, or that bucket-list adventure you’ve been dreaming of.
Dive to discover colorful corals
Few travel styles complement each other as perfectly as diving and sailing! Explore vibrant reefs up close with an exhilarating dive, then unwind on deck with a refreshing drink as you soak in the surroundings.
Sail the Egyptian way on a felucca
Experience the mysteries of the Nile aboard a traditional wooden sailing boat. Enjoy delicious Middle Eastern cuisine and luxurious comfort as your journey transports you back to the era of the pharaohs.
Sail the Egyptian way on a felucca
Discover the secrets of the Nile aboard a traditional wooden sailing boat. Savor authentic Middle Eastern cuisine and enjoy unparalleled comfort as your journey brings the ancient world of the pharaohs to life.
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Your Sailing trip questions, answered
Do I need to know how to sail?
On most of our sailing adventures, a skipper or crew members will be on board to guide you, so no prior sailing experience is needed. If you’re interested in taking the helm yourself, some private sailing trips offer the chance to captain your own boat—just be sure to check with your operator to see if this option is available.
Am I required to help out on the boat?
Sailing adventure operators come with a fully skilled crew, so you can relax without needing to pitch in—unless you’re eager to sharpen your sailing skills, of course!
What are the cabins like?
Cabin sizes vary depending on the vessel, but they’re generally compact. Couples usually have their own cabin, while solo travelers may share with another passenger of the same gender or pay a single supplement for a private room. Most cabins feature ensuite bathrooms, though some boats may have shared facilities. If you’re unsure, your operator can provide all the details.
How much time is spent off the boat?
Sailing tours perfectly balance life on and off the water. A typical day might start with waking up on board, taking a refreshing morning swim, then docking at a historic port to explore charming streets, sample local cuisine, and enjoy some free time before returning to your boat for the evening. Each sailing itinerary is unique, but most include guided excursions and a variety of land-based activities along the way.
Do I need travel insurance for a Sailing trip?
Most Overland trips include setting up tents, helping with meal prep, spending long hours on the road, and navigating bumpy terrain, so a moderate level of fitness is recommended to make the most of your adventure. If you’re unsure about the activity level, our Travel Experts are happy to advise you. And if you’re craving something more active, consider adventures that include thrilling experiences like ziplining through the jungle or cooling off with a refreshing dive!
How do I book a Sailing adventure on Tossntrip?
Find your next sailing adventure by browsing our tours—choose your preferred dates and destination, and use our easy filters for must-see cities or budget to discover the trip that’s calling your name. Once you’ve found it, just enter your details to secure your spot. And if you have any questions, our Travel Experts are available 24/7 to help!