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
4.8
out of 5 based on 259 reviews submitted.
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Sail Greece: Santorini to Mykonos
Kathryn · Traveled June 2024
Fabulous trip of a lifetime. There are some small discomforts to living on a boat but they are more than made up for by the incredible experience of it all. Swim stops in secluded coves were a highlight. Beds were surprisingly comfortable.
Review submitted 11 Jul 2024Sail Greece: Santorini to Mykonos
Katlyn · Traveled June 2024
This trip well and truly exceeded my expectations. The other members of the group as well as our skipper made for a magical week sailing around the Cyclades and I wouldn’t hesitate to book it again!
Review submitted 08 Jul 2024Greece Sailing Adventure: Cyclades Islands
Lorna · Traveled June 2024
Sailing through the Small Cyclades of Greece with our skipper, Jorg, was like a dream. He is a phenomenal sailor-hospitable and knowledgeable, with an award winning smile. The Mediterranean sights, sounds, and culture fed my soul. Glorious, crystal clear swimming spots, melty sunsets, delicious seafood. Thank you, Skipper Jorg!
Review submitted 11 Jul 2024Greece Sailing Adventure: Cyclades Islands
Patrick · Traveled June 2024
This was an amazing adventure for my family and I! One filled with nature, culture, and adventure. We made memories that Ivwilk always cherish for the rest of my life!
Review submitted 07 Jul 2024Sail Greece: Mykonos to Santorini
Rick · Traveled June 2024
My family of 6 spent 7 amazing days sailing the Greek islands with Intrepid. We had the most amazing experiences with a brilliant skipper, his wealth of knowledge on the islands you visit, his recommendations on places to see and eat at and the amazing locations he takes you to swim in crystal clear waters. It’s a 20/10 for us. Thank you Intrepid and thank you to our amazing skipper Nikos.
Review submitted 10 Jul 2024