Sailing Trips

Embark on a sailing adventure along the Dalmatian coastline, island hop Greece, journey along the Turkish Riviera, or soak up the sun from your yacht moored off the beautiful beaches of Thailand. Enjoy water activities from kayaking to paddle boarding, discover incredible ports, swim straight off your sailing boat, and kick back for sundowners on the deck on one of our 60 sailing trips around Asia, Europe and the Caribbean.

Popular Trips View all

10 Days Split to Split

Operator: Intro Travel

From 2,232pp
Save 122pp

8 Days Dubrovnik to Split

Operator: Intrepid Travel

From 2,119pp
Save 69pp

10 Days Santorini to Santorini

Operator: Intrepid Travel

From 2,877pp
Save 94pp

15 Days Dubrovnik to Split

Operator: G Adventures

From 2,647pp
Save 1,252pp

Discover Popular sailing experiences and highlights around the world

Kayak Halong Bay
Kayak Halong Bay

Paddle between the towering karsts of Halong Bay, marvelling at this wonderland of secluded bays, intriguing cave systems, floating villages and limestone pillars.

<a href='/tours/croatia/sailing' class='u-link'>Dive into the Adriatic</a>
Dive into the Adriatic

The azure water beckons as you pull up for swim stops between exploring the historic ports and natural wonders of Croatia on a sailing trip along the Dalmatian coast.

Caribbean Sunsets
Caribbean Sunsets

Watch the sun set on a day of snorkelling the clear waters of the Caribbean. A daily delight on your Cuban sailing adventure through the Canarreos Archipelago.

Treasures of Thailand
Treasures of Thailand

Discover iconic beaches and hidden gems only accessible by boat as you call the waters off Thailand home. Swim in the turquoise water by day and, should you choose, sleep on the deck under the stars by night.

Aegean Vistas
Aegean Vistas

Island hop through the Greek Islands, strolling the charming coastal villages and dining in local tavernas. Take in sweeping views from whitewashed terraces as a puzzle of blue and white fit together perfectly before you.

Recent Reviews What our clients are saying about their sailing and island hopping adventures

Sailing in Croatia? Croatia Sailing Adventure: Dubrovnik to Split , NSW, Australia, Aug 2025
Firstly, Tracey did a great job (as usual) booking this trip for us. Unfortunately, we were a bit disappointed in the trip that Intrepid provided. We visited some wonderful locations during our 8 days, but only sailed for about 4 hours during the whole trip. Had we not prompted the skipper to raise the sails, we would probably have sailed even less.... read more There was always an excuse that there wasn’t enough wind, or there was too much wind, or the wind was from the wrong direction. This was even though there were yachts all around us under sail. We could only conclude that it was too much effort to sail the yacht.

We made a complaint to Intrepid, and they have advised that they have updated the notes for the trip to now indicate that it is possible that the skipper will need to use the motor for the entirety of the trip (pending weather conditions and the skipper's direction).
Fascinating sailing trip in Dalmatia and Montenegro   Montenegro & Croatia Sailing , BC, Canada, Jun 2025
Wonderful crew of diverse folks, great skipper, perfect weather, unique experiences on the sea and land. I highly recommend Global Journeys and would use them again!
Sailing the Cyclades Greece Sailing Adventure: Cyclades Islands , VIC, Australia, Sep 2023
Fantastic sailing trip, visited 8 beautiful islands. You sail in the morning wind permitting for around 4/6 hours arriving at the next island in plenty of time to explore and enjoy dinner. Our skipper Fotis was local and we always felt safe in his capable hands. The yacht is 56 feet so you don’t have very much sleeping and bathroom space, you need to... read more be prepared for that. Highly recommend this Intrepid trip.
Croatia Sail Adventure Croatia Sail Adventure , Australia, Sep 2023
My friends and I had an amazing time on the Croatia sailing adventure! Becca, our guide, was knowledgeable, spazzy (in a fun way), and overall absolutely amazing. She was able to find fun things for us to do when the weather wasn't ideal, and helped all the different group of people intermingle and become lifelong friends. We loved walking the wall... read more of Dubrovnik and falling off inflatable rafts at a floating waterpark. Overall a great trip!

Trip Lengths