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!

Our Greece sailing cruises

**Prices and savings are based on the lowest priced upcoming departure for each trip, which may reflect discounts outside of the current sale. Prices are updated every 12 hours and are valid until sold out. Discounts apply to selected departures only and may be applied, modified or withdrawn at any time at Intrepid's absolute discretion. Read the terms and conditions or learn more about pricing
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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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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

4.9 . 545 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: Cyclades Islands

Claire
Traveled October 2025

Greece Sailing Adventure: Cyclades Islands

Stacey
Traveled October 2025

Greece Sailing Adventure: Cyclades Islands

Mike
Traveled October 2025

Greece Sailing Adventure: Cyclades Islands

Pieter
Traveled October 2025

Sail Greece: Santorini to Mykonos

Julia
Traveled October 2025

Frequently asked questions