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 61 sailing trips around Asia, Europe and the Caribbean.
Popular Trips View all
10 Days Santorini to Santorini
Operator: Intrepid Travel
From 2,178
Save 591
7 Days Phuket to Phuket
Operator: G Adventures
From 1,572
Save 277
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.
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
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.
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!
My husband and I did sail Croatia for a week of my birthday. Although I was hesitant about being a bit older for sail Croatia (33), and also being a married couple we didn't really know what to expect. We had the best time of our life with our group, Dom (our leader), and the Trutravels team! It was so well organised, it was a good mix of party and ...read more learning about the places and doing fun activities (e.g. White water rafting, bike riding, clubbing in a cave and a castle!) albiet there was definitely a lot more party vibes with our particular group. A good mix of ages (19-35) and from all backgrounds - UK, Australia, France, Germany, Canada, Scotland.
Dom, our fearless leader, was absolutely incredible!! He was so quick with responses, always had an answer for any questions we had and was on the case when there was any issues that would arise. Two people had family emergencies during the week and he was quick to do whatever he could for both of them to help. It was obviously that he really cared about making the whole trip the best experience for all of us, whether that was having a chill night playing cards but also raging in the bar or clubs with the rest of us but also organising us all so we were safe and all having the best time! He also managed to give us enough free time between group activities to have breaks and gave us enough historical information to be informed about the amazing places we visited while also joining in on the activities with the rest of the group. He was sweet, funny, kind, caring, passionate, knowledgeable and we could not have asked for a better leader for our team! Love you Dom!
The crew on board were also so helpful, smiling and happy to accommodate us (as they live full time on board, it must be hard to have a party every night in your home). They worked so hard when we were ringing that bell for rounds of shots every 2 minutes!! And we love them for it!
The boat itself is intimate to say the least but it meant that we were all like family by the end. A few different areas to hang out in and separate to have your our space too. The bedrooms were a bit small (all single bunks) with not a lot of floor space but can store shoes and bags under the bed and small hanging space. Has a great aircon! The bathroom sink converts into a hand-held shower which has good hot water and pressure as long as not too many people using it at once.
The only other comment is that the bar tab at the end has to be paid in full cash at the end of the last night and a few people got caught up with big bar tabs and limited cash withdrawals which we had been warned about so FYI to take out your cash in advance and keep on eye on your tab! All in all, an amazing week with an amazing crew an awesome team of people!
Dom, our fearless leader, was absolutely incredible!! He was so quick with responses, always had an answer for any questions we had and was on the case when there was any issues that would arise. Two people had family emergencies during the week and he was quick to do whatever he could for both of them to help. It was obviously that he really cared about making the whole trip the best experience for all of us, whether that was having a chill night playing cards but also raging in the bar or clubs with the rest of us but also organising us all so we were safe and all having the best time! He also managed to give us enough free time between group activities to have breaks and gave us enough historical information to be informed about the amazing places we visited while also joining in on the activities with the rest of the group. He was sweet, funny, kind, caring, passionate, knowledgeable and we could not have asked for a better leader for our team! Love you Dom!
The crew on board were also so helpful, smiling and happy to accommodate us (as they live full time on board, it must be hard to have a party every night in your home). They worked so hard when we were ringing that bell for rounds of shots every 2 minutes!! And we love them for it!
The boat itself is intimate to say the least but it meant that we were all like family by the end. A few different areas to hang out in and separate to have your our space too. The bedrooms were a bit small (all single bunks) with not a lot of floor space but can store shoes and bags under the bed and small hanging space. Has a great aircon! The bathroom sink converts into a hand-held shower which has good hot water and pressure as long as not too many people using it at once.
The only other comment is that the bar tab at the end has to be paid in full cash at the end of the last night and a few people got caught up with big bar tabs and limited cash withdrawals which we had been warned about so FYI to take out your cash in advance and keep on eye on your tab! All in all, an amazing week with an amazing crew an awesome team of people!
I went on the Croatia Sail tour and had one of the best holidays ever! There was a good balance between chill time on the boat and activities - such as kayaking, cycling in a beautiful national park, swimming in the sea at the daily swim stops, sightseeing and going out to Croatian bars/clubs (if you wanted to). The boat was great and the views of the ...read more sea and Croatian coastline every day were frankly incredible. Special thanks to the group leaders, Anna and Becca! They both had great energy, ensured everything went smoothly and that everyone felt included. Anna is also an encyclopedia on Croatia! If you are in two minds about going, I strongly recommend that you just book it! I can't believe how good the trip was! Thank you again Anna and Becca for such an amazing experience.
