Greece sailing cruises

Blue coves, white beaches, islands both big and small – to explore this slice of paradise, you’re gonna need a boat

You know those moments in life when you wonder, is this even real? On a sailing trip to Greece’s Cyclades Islands, that happens a lot. It strikes when you wake up in the Mediterranean and dive in for a swim. When you sail into Mykonos and realise that big rock over there is actually the petrified body of a giant once defeated by Hercules (or so the legend goes). You’ll feel it when you dock off the coast of a deserted island, when you get lost in the white-washed streets of Apollonia, or when you share a shot of ouzo with a local fisherman. But trust us, it’s real. And it’s waiting for you.

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Greece sailing highlights

Our boats

Ocean Star 56 Boat
Ocean Star 56
The Ocean Star 56  is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, the Ocean Star 56 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins, 2 twin cabins and 1 triple cabin,  the Ocean Star 56 is the perfect yacht for novices to learn the ‘ropes’.
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4.8 out of 5 based on 217 reviews submitted.
Reviews are from travellers who have completed their trip and want to share their experience. We show all reviews, but may remove any that include profanity or inappropriate content, are unrelated to the trip or reveal personal details.

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Sail Greece: Mykonos to Santorini

Amanda · Traveled May 2024
A truly wonderful trip led by an outstanding Skipper with a lovely group.
Review submitted 01 Jun 2024

Sail Greece: Santorini to Mykonos

Meaghen · Traveled May 2024
Orestis made the trip. We ended up with a great group, but he was the highlight. He was very knowledgeable of every island we visited and gave us options for what we wanted to eat/see and didn’t mislead us once. He was very safe while also being laid back and fun. He is a kind and wonderful, but also very knowledgeable about sailing and safety. I cannot say enough! 10/10 will book Intrepid again because of the experience he gave us.
Review submitted 25 May 2024

Sail Greece: Santorini to Mykonos

Lauren · Traveled May 2024
This trip was one for the bucket list!! So amazing and filled with wonderful places & people!! Skipper Orestis was the cherry on top!! We would do it all over again in a heartbeat!!
Review submitted 25 May 2024

Sail Greece: Santorini to Mykonos

David · Traveled May 2024
Time of my life. Highly recommend. Was lucky to have a great skipper and also other great travellers.
Review submitted 23 May 2024

Greece Sailing Adventure: Cyclades Islands

Andre · Traveled May 2024
Don’t think twice. Do it. Trip of a lifetime and more than lives up to its expectations. You will fall in love with all the islands!
Review submitted 23 May 2024

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