Greece sailing cruises
Blue coves, white beaches, islands both big and small – to explore this slice of paradise, 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 in 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 Greece sailing cruises
Greece sailing highlights
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?
Catch a Santorini sunset
Santorini ticks all the dream vacation boxes. You’ve got volcanic beaches. Cathedrals and historic 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.
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.
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.
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’. Reviews
4.9
out of 5 based on 273 reviews submitted.
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.
Filter by rating
Sail Greece: Mykonos to Santorini
Joaquin · Traveled July 2024
I loved every aspect of this trip. If you want to experience a unique way of sailing the Cyclades, this is one you won't regret. Thank you Jörg, for an unforgettable adventure.
Review submitted 27 Jul 2024Greece Sailing Adventure: Corfu to Kefalonia
Richard · Traveled July 2024
I loved this trip. Our skipper Loukas was very professional and the group of people were wonderful. If you are comfortable with the boatlife then you will love seeing these beautifull Islands, swimming in the blue waters and eating amazing greek food. I recommend you talking with the group about buying a shared SUP-board or some other oceangadget, if you find space on the boat.
Review submitted 28 Jul 2024Greece Sailing Adventure: Cyclades Islands
Amanda · Traveled July 2024
Sailing. What an adventure. A fantastic way to travel around the Greek islands. They are amazing to see particularly some of the smaller islands. If you’re looking for an adventure which takes you slightly out of your comfort zone then I would highly recommend this trip.
Review submitted 27 Jul 2024Greece Sailing Adventure: Cyclades Islands
Caitlin · Traveled July 2024
This trip was awesome. I’ve never sailed before and our captain Niko really made sure we all knew what was happening and when. Having his knowledge of the Islands truly made the trip special. 10/10 would recommend.
Review submitted 28 Jul 2024Sail Greece: Mykonos to Santorini
Paul-Marie · Traveled July 2024
Phenomenal experience, some of the most beautiful sights of my life. Tour facilitator took amazing care of the group and really made the trip.
Review submitted 23 Jul 2024