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.

Europe Sailing

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’.
Explore features

Reviews

4.9 out of 5 based on 296 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.

Filter by rating

Sail Greece: Mykonos to Santorini

Veronica · Traveled August 2024
This trip was so amazing and George our cap was simply the best. From his knowledge of the sea, whether boat, history of Greece we had the trip of a lifetime. Thank you, George.
Review submitted 10 Aug 2024

Sail Greece: Mykonos to Santorini

Lissa · Traveled August 2024
Great trip and awesome experience. Highly recommend it to anyone. If you are traveling in the high season I recommend bringing a sun umbrella for the beach as there isn't much shade around.
Review submitted 10 Aug 2024

Sail Greece: Mykonos to Santorini

Courtney · Traveled August 2024
Absolutely amazing way to see the islands. Incredible captain Jorg was beyond helpful and always smiling! Only delicious food and beautiful views. The best part is the swim stops to snorkel. My only recommendation is to travel when it’s a little cooler. August was too hot for sleeping with air conditioning when there is weaker winds.
Review submitted 10 Aug 2024

Sail Greece: Mykonos to Santorini

Stefan · Traveled August 2024
Great experience overall worth every penny. The skipper Jörg was great, very knowledgeable and his energy made the trip. I would do it again!
Review submitted 10 Aug 2024

Sail Greece: Mykonos to Santorini

Andrew · Traveled August 2024
Review submitted 15 Aug 2024

Frequently asked questions