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
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


4.8 out of 5 based on 222 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: Santorini to Mykonos

Montserrat · Traveled May 2024
Amazing clear waters, beautiful monasteries, fantastic sailing boat, delicious food and the greatest skipper (Orestis) you could imagine. Awesome trip :)
Review submitted 05 Jun 2024

Greece Sailing Adventure: Cyclades Islands

Hannah · Traveled May 2024
Great way to explore Greece. Especially for those who love being on and in the water. Big thank you to George!
Review submitted 06 Jun 2024

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: Mykonos to Santorini

Pam · Traveled May 2024
INCREDIBLE!!!! This was our 2nd year sailing from Mykonos to Santorini. Our 1st year was so awesome we repeated the same trip. We didn’t think it could get any better, but it did! Our skipper, Nikos, was phenomenal and we would sail again with the other mates! The islands and swim spots are amazing! Sailing the Aegean Sea is a dream!!! Thanks Nikos for taking such great care of us and for your kindness, laughs, and wonderful time on Sophia!
Review submitted 05 Jun 2024

Sail Greece: Mykonos to Santorini

Rachel · Traveled May 2024
To say this trip was marvelous is an understatement. This trip is a must if you want to see the beautiful, Greek islands in an intimate and meaningful way.
Review submitted 05 Jun 2024

Frequently asked questions