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 205 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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Markus · Traveled May 2024
Very nice sailing experience in the small Cyclades. Great skipper with a lot of local knowledge! Beautiful boat "Serendipity". Great group of travellers..
Review submitted 14 May 2024

Rachel · Traveled May 2024
A beautiful experience visiting a range of different Cycladic islands with lots to offer. Plenty of free time to explore and choose things to do based on your interests and abilities. Amazing sailing too and the most stunning views everywhere you look. Highly recommended!
Review submitted 14 May 2024

Courtney · Traveled May 2024
This trip was truly amazing! The islands were beautiful and the sights we saw were incredible. The sailing part was so much fun and truly unforgettable
Review submitted 13 May 2024

Ashlee · Traveled May 2024
If you are wondering if this trip actually sails, the answer is absolutely yes! We sailed alot because the weather gave us perfect conditions. The boat, the skipper (Fotis), the other travelers, the weather, the islands were all fantastic and I highly recommend this trip. If you are going early to mid May though pack warm clothes because it's cooler than you might think. Happy sailing!
Review submitted 13 May 2024

Leslie · Traveled May 2024
Hands down great sailing trip where you actually sail. The boat is nicely set up to provide privacy as much as possible in the small space. Captain Fotis is a skilled skipper, great story teller and shares historical tidbits about the islands you visit. We had great group dynamics and did family style dinners with Fotis at restaurants on the various islands. Hands down one of my top vacations post empty nest.
Review submitted 13 May 2024

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