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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 56 sailing trips around Asia, Europe and the Caribbean.

Popular Trips View all

Croatia Sailing Adventure

8 Days Split to Split

Operator: TruTravels

From 2,347

Save 52

Wineglass Bay Sail Walk (Signature)

6 Days Hobart to Hobart

Operator: Tasmanian Walking Co

From 4,450

Save 50

Croatia Sailing Adventure: Split to Dubrovnik

8 Days Split to Dubrovnik

Operator: Intrepid Travel

From 2,945

Save 68

Sail & Swim: Greece

8 Days Athens to Athens

Operator: Topdeck

From 2,939

Save 67

Discover Popular sailing experiences and highlights around the world

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.

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

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

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

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 the Cyclades Julie, 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

Wineglass Bay Signature Walk Karen Stewart, VIC, Australia, Apr 2023

I had a wonderful time on the trip, particularly enjoying the sailing between our walking days. The entire trip was characterized by wonderful scenery, regardless of the weather. The days were well planned, with a good mix of harder and easier walking days, which kept things interesting. I also appreciated the special touches like the oysters and champagne ...read more

Smoothly run sightseeing Renee, New Zealand, Jul 2018

This trip was highly organised, I never had to worry about any of the logistics that you have when organising your own travels. I was able to simply just lay back and relax, and enjoy the amazing sights! Global journeys were a hassle free company to book this trip through. I had no problems with them and they were always prompt to reply.

The Greek islands are very beautiful Jennifer Yip, Australia, May 2013

This tour was great fun. The tour manager was really nice and friendly and everyone in the group was also really fun and always up for a good time. The cruise was very relaxing and all the ports we visited were great. The buffet meals were all pretty decent and for 80 euros, it was a great deal for unlimited drinks over the 4 days on the cruise. The ...read more