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 in 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

10 Days From $1,711

See the best of the Cyclades Islands on this Greece sailing adventure. Take to the...

8 Days From $1,411

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

8 Days From $1,411

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

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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Sunsets in Santorini.

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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Seaside views at a Greek restaurant.

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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Naxos is full of history.

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

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

'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

Kutte has been a sailing instructor since 1975.

FAQs

Click here to see Europe Sailing FAQs

Reviews

Greece Sailing Adventure - Cyclades Islands , September 2017

Grace Cho

Greece Sailing Adventure - Cyclades Islands , September 2017

Nathanael Palmatier

Sail Greece - Mykonos to Santorini , October 2017

Michael Ciacco

Sail Greece - Mykonos to Santorini , October 2017

Sharon Head

Greece Sailing Adventure - Cyclades Islands , September 2017

Jennifer Graham

Greece Sailing Adventure - Cyclades Islands , September 2017

Douglas Halberg

Sail Greece - Santorini to Mykonos , September 2017

jessica mooyman

Sail Greece - Mykonos to Santorini , September 2017

Pauline Chan

Greece Sailing Adventure - Cyclades Islands , September 2017

Kaleda Clarke

Sail Greece - Mykonos to Santorini , September 2017

Tina Morosoli

Sail Greece - Mykonos to Santorini , September 2017

Nichola Higgins

Sail Greece - Mykonos to Santorini , September 2017

Robert Hollander

Greece Sailing Adventure - Cyclades Islands , September 2017

Tristan Klosterman

Greece Sailing Adventure - Cyclades Islands , September 2017

william lynch

Greece Sailing Adventure - Cyclades Islands , August 2017

Amber Hough

Sail Greece - Santorini to Mykonos , September 2017

Lindsey Payson

Greece Sailing Adventure - Cyclades Islands , August 2017

Patrick Taggert

Greece Sailing Adventure - Cyclades Islands , August 2017

Sam Plant

Sail Greece - Santorini to Mykonos , August 2017

Alexandra Penman

Greece Sailing Adventure - Cyclades Islands , August 2017

Georgina Sawyer

Greece Sailing Adventure - Cyclades Islands , July 2017

Susan McAleer

Greece Sailing Adventure - Cyclades Islands , August 2017

Susan Blake

Greece Sailing Adventure - Cyclades Islands , July 2017

Gabrielle Harrison

Greece Sailing Adventure - Cyclades Islands , July 2017

Brooke Pisani

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