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 realize 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
4.8
out of 5 based on 203 reviews submitted.
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Courtney · Traveled May 2024
This trip was truly amazing! The islands were beautiful and the sights we saw were incredible. The sailing part was so much fun and truly unforgettable
Review submitted 13 May 2024
Ashlee · Traveled May 2024
If you are wondering if this trip actually sails, the answer is absolutely yes! We sailed alot because the weather gave us perfect conditions.
The boat, the skipper (Fotis), the other travelers, the weather, the islands were all fantastic and I highly recommend this trip. If you are going early to mid May though pack warm clothes because it's cooler than you might think. Happy sailing!
Review submitted 13 May 2024
Leslie · Traveled May 2024
Hands down great sailing trip where you actually sail. The boat is nicely set up to provide privacy as much as possible in the small space.
Captain Fotis is a skilled skipper, great story teller and shares historical tidbits about the islands you visit. We had great group dynamics and did family style dinners with Fotis at restaurants on the various islands.
Hands down one of my top vacations post empty nest.
Review submitted 13 May 2024
Carol · Traveled October 2023
As a solo mature female passenger on this trip I felt well informed and safe.
George our skipper was very helpful and very patient overall he made the trip enjoyable .
Highly recommend an escape and a chance to reset.
Review submitted 09 Oct 2023
Andy · Traveled October 2023
I quite enjoyed our seven day sail through the Greek isles. Our captain had a dry sense of humor, exhibited great confidence in the handling of the boat and management of all his passengers’ various needs. He made the trip easy, with multiple recommendations, and options for excursions. We learned quite a bit of the local mythology, lore, and history. I would highly recommend this trip to even novice sailors, such as myself.
Review submitted 09 Oct 2023