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
PASSENGERS: 11
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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Reviews

4.8 out of 5 based on 237 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

Natalia · Traveled June 2024
Best trip ever! Very well organised, very safe and comfortable and we visited amazing locations. Our guide was excellent and made our trip very enjoyable. We’ll be travelling with Intrepid again in the future, Thank you Nikos and Intrepid!
Review submitted 17 Jun 2024

Greece Sailing Adventure: Cyclades Islands

Viktoria · Traveled June 2024
The sailing trip was just wonderful, fresh air and the sea completely refreshed my body and mind.If you get Jorgus as your team leader you will be sailing through amassing spots for snorkeling , and always eat at the best restaurants
Review submitted 16 Jun 2024

Greece Sailing Adventure: Cyclades Islands

Patrick · Traveled June 2024
This cruise was the perfect way to see the best of the Cyclades. The skipper was of the highest quality - incredibly gifted at sea, had extensive knowledge of the islands and sailing routes, was accomodating to all passengers and preferences, and made the whole experience worthwhile and enjoyable. I’d recommend this to anyone wanting to see the beauty of the Greek Isles!
Review submitted 17 Jun 2024

Sail Greece: Mykonos to Santorini

Joshua · Traveled June 2024
Can’t recommend this trip enough, great way to experience the Greek islands.
Review submitted 12 Jun 2024

Greece Sailing Adventure: Cyclades Islands

Glenn · Traveled June 2024
A great experience sailing in the Greek Islands - the trip was everything we hoped for & travelling with a small group was great
Review submitted 14 Jun 2024

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