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 314 reviews submitted.
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Greece Sailing Adventure: Cyclades Islands
Sally · Traveled August 2024
Loved every minute of this sail ,thanks to Jorg our awesome skipper. He even caught and cooked us a fish 😀
Review submitted 31 Aug 2024Greece Sailing Adventure: Cyclades Islands
Jessica · Traveled August 2024
Jorg and the Greece sail was the dream experience. Cosy snorkel spots, local tavernas and time to wind down. Jorg kept us safe and had great respect for the ocean. I am taking up sailing after this trip! Thank you
Review submitted 02 Sep 2024Sail Greece: Santorini to Mykonos
Julius · Traveled August 2024
An absolutely incredible experience. To anyone thinking about sailing the Cyclades with Intrepid, stop thinking and start booking!
Review submitted 29 Aug 2024Greece Sailing Adventure: Corfu to Kefalonia
Alessandra · Traveled August 2024
If you are looking for an trip combining beautiful islands, pristine beaches, turquoise sea, and yet a place somehow off the beaten path look no further! You have it all in this trip. Sailing the Med on a boat is the ultimate experience that will heal your body as sooth your soul.
Review submitted 01 Sep 2024Sail Greece: Mykonos to Santorini
Perry · Traveled August 2024
A gorgeous week of sailing, sunbathing, eating incredible food, and watching gorgeous sunsets with new friends! Our skipper Nikos was the absolute best- he worked HARD every day to keep us safe and make sure we had the best experience possible. I would definitely recommend to pack very lightly (but don’t forget sunscreen and a beach towel!)- the cabins do have limited space but it was surprisingly comfortable and had everything we needed!! Overall this is the perfect trip if you are interested in exploring many islands of Greece beyond the typical tourist route. I would also recommend booking an extra day or two in Santorini at the end if possible!
Review submitted 25 Aug 2024