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 254 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

Leah · Traveled June 2024
This trip was a great experience across the board!! Fotis is an amazing Skipper and we highly recommend him to all travelers to find the roads less traveled and the opportunities you could not imagine on your own. 10/10 experience!
Review submitted 25 Jun 2024

Sail Greece: Mykonos to Santorini

Morgan · Traveled June 2024
This trip is perfect for adventurous travelers who want a little bit of everything in an island trip!
Review submitted 25 Jun 2024

Sail Greece: Mykonos to Santorini

Will · Traveled June 2024
I had an excellent trip with our group tour, sailing the islands of Greece. Highly recommend Fotis as a captain. He’s great with island recommendations and giving you a great experience exploring the Greek islands.
Review submitted 25 Jun 2024

Sail Greece: Mykonos to Santorini

Evan · Traveled June 2024
Great trip. Fotis the captain was incredible. What a beautiful journey
Review submitted 25 Jun 2024

Greece Sailing Adventure: Cyclades Islands

Philip · Traveled June 2024
Sailing trip was beyond all expectations. One of the most memorable holidays I have had. Our captain, Giorgios was amazing. Had all the local knowledge and his recommendations were excellent. Giorgios was a big part of making the trip so enjoyable and I now have a new Greek friend. Yammas Giorgios.
Review submitted 27 Jun 2024

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