Greece sailing cruises

To explore the Greek islands, you’re gonna need someone who knows their way around

Turns out, we know a legendary local skipper or two. Sailing in Greece is full of pinch-me moments. It hits when you’re clipping across the Aegean with the salty sea breeze in your hair, swimming in electric-blue coves or sipping ice-cold ouzo with locals in a fishing village. And those sunsets from the deck? They never get old. These trips are beginner-friendly, so there's no need to know your knots or how to hoist sails – though there’ll be time to learn if you're keen. All you need is an adventurous spirit. Anchor’s up!

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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Ocean Star 51.2 Boat
Ocean Star 51.2
The Ocean Star 51.2  is a classic sailboat with exceptional seaworthiness, combining timeless design with plenty of comfort. Fashioned with a traditional wood interior, the Ocean Star 51.2 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins and 2 twin bunk cabins,  the Ocean Star 51.2 is the perfect yacht for novices to learn the ‘ropes’.
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Reviews

4.9398 reviews
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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Greece Sailing Adventure: Kefalonia to Corfu

Richard (Steve) · Traveled May 2025
Review submitted 02 Jun 2025

Greece Sailing Adventure: Kefalonia to Corfu

Rosemary Jane · Traveled May 2025
Review submitted 01 Jun 2025

Sail Greece: Mykonos to Santorini

Rebecca · Traveled May 2025
Review submitted 02 Jun 2025

Sail Greece: Mykonos to Santorini

Ashlee · Traveled May 2025
Review submitted 27 May 2025

Sail Greece: Mykonos to Santorini

Tamra · Traveled May 2025
Review submitted 27 May 2025

Frequently asked questions