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
Greece sailing highlights
Hike Santorini's caldera rim
Santorini ticks all the boxes: volcanic coastlines, iconic blue-domed buildings, great shopping and seaside dining. But the biggest drawcard? To-die-for views. After sailing around the Cyclades, consider sticking around to hike the caldera rim – where cliffs plunge into the Aegean – or relax on black-sand beaches.
Explore quieter islands
If your vision of the Greek Islands is less beach clubs and more sleepy fishing villages, you’ll be right at home in the Small Cyclades. Fewer tourists visit this dreamy archipelago, meaning you can wander barefoot along empty beaches, swim in deserted bays and get to know the locals in family-run tavernas.
Join the party in Mykonos
If there’s anywhere that’s got hedonism down to a fine art, it’s Mykonos. Named after Apollo’s grandson, this shining star of the Cyclades offers a little bit of everything – chic boutiques, some of Europe's top-rated beaches, divine food and world-renowned nightlife. And how better to roll into town than on a yacht?
Geek out on history in Naxos
You’ll feel as if you’ve stumbled right back to the Middle Ages as you wander Naxos’ tangle of laneways, churches and hilltop castles. Mythology runs deep here too – Zeus (king of the gods) supposedly grew up here, and it’s said that Naxos is where Dionysos (god of wine and fertility) fell in love with princess Ariadne, daughter of King Minos of Crete.
Recharge in Corfu
Nicknamed the Queen of the Ionian Islands, Corfu is the perfect place to recharge. If you can peel yourself away from its pristine beaches, you might find yourself getting lost in the lanes of its UNESCO-listed Old Town, exploring Venetian fortresses, hiking through centuries-old villages or wandering the grand Palace of St. Michael and St. George.
Our boats
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’.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’.Reviews
4.9 . 515 reviews
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Sail Greece: Mykonos to Santorini
Tina
Traveled September 2025
Sail Greece: Mykonos to Santorini
Jeremy
Traveled September 2025
Greece Sailing Adventure: Kefalonia to Corfu
Rachel
Traveled September 2025
Greece Sailing Adventure: Cyclades Islands
Jay
Traveled September 2025
Greece Sailing Adventure: Cyclades Islands
Eugenie
Traveled September 2025