Greece Sailing Tours & Vacations

Blue coves, white beaches, islands both big and small – to explore this slice of paradeisos, 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 on 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.

Our sailing tours in Greece

Greece Sailing Adventure: Cyclades Islands

10 Days From 3020

See the best of the Cyclades on this 10-day Greece sailing adventure. From Athens to...

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Sail Greece: Mykonos to Santorini

8 Days From 2050

Embark on a sailing holiday to Greece. Explore the waters, islands, history and cuisine...

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Sail Greece: Santorini to Mykonos

8 Days From 2050

Set sail across the Mediterranean exploring Greece's heaven-sent islands. The spoils of...

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Greece Sailing Adventure: Corfu to Kefalonia

8 Days From 2567

Take a sailing trip on the Ionian Sea through the waters of Greece. Sail from Corfu to...

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Greece Sailing Adventure: Kefalonia to Corfu

8 Days From 2567

Take a sailing trip on the Ionian Sea through the waters of Greece. Sail from Kefalonia...

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Tailor-Made trips

Take four or more on an exclusive trip and tailor your itinerary

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Highlights of Greece sailing

Experience the famous nightlife on Mykonos.

Join the party on Mykonos

If there’s anywhere that’s got hedonism down to a fine art, it’s the sunny isle of Mykonos. Named after Apollo’s grandson, this shining star of the Cyclades presents the holidaymaker (that’s you) with pleasures galore – chic boutiques, sandy beaches, divine food and world-class nightlife. And how better to roll into town than on a yacht?

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Catch a Santorini sunset

Santorini ticks all the dream holiday boxes. You’ve got volcanic beaches. Cathedrals and historical sites. Boutique shopping and seaside dining. But mostly, views. Everywhere you look, you’ll catch to-die-for views across the white-tipped cliffs of the caldera and down to the Aegean Sea. Make sure you do the famous walk from Fira to Oia, arriving just in time for a sunset cocktail.

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Escape to the Small Cyclades

If your vision of the Greek Islands is less mega nightclubs and more sleepy fishing villages, you’ll be right at home in the Small Cyclades. Few tourists frequent this dreamy archipelago, where the total population numbers in the low hundreds. Wander barefoot along empty beaches, watching out for dolphins in the distance, then sit down to a seafood feast by the water.

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Meet history on Naxos

History buffs will be at home on Naxos. Apollo, Dionysos, Ares and Zeus all have strong ties to the island, while some versions of Greek mythology even suggest Zeus – king of the gods – grew up here. In the 1200s the island was taken by the Venetians. Wandering through the town’s tangle of laneways, churches and castles, you’ll feel as if you’ve stumbled right back into the Middle Ages.

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Our boats

Ocean Star 56

In Greece, you’ll be travelling aboard the Ocean Star 56. Designed and built in Greece, this comfortable, stylish yacht features 5 cabins, a spacious cockpit and roomy saloon with U-shaped seetee. Welcome to your home on the sea!

Click here to see the deck plan

Meet your skipper

Kutte has been a sailing instructor since 1975.

'I love the freedom of sailing. I learned to sail in a rubber dinghy with a small sail, and from there I became a sailing instructor in Corsica in 1975. I’ve sailed the Caribbean, but now I mostly sail the Mediterranean Sea. I like island hopping and exploring islands with their unique harbour villages and beautiful bays. I believe to really get the most out of your sailing adventure you must be flexible, forgiving, helpful and authentic.' – Kutte, Cyclades Islands