Sailing in Greece
Set sail for a Greek island odyssey. Discover Mykonos, with its famous windmills, wander through the ancient temples of Naxos, and check out Syros's beautiful architecture. Of course, don't forget to get some R&R on Ios's pristine beaches. Watch spectacular sunsets from Santorini's caldera, tour Athens' Acropolis, swim in turquoise waters at Paros and the Saronic Gulf, and savor fresh seafood at harbor-side taverns. What a life!
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Peter • traveled in October
We had a great time meeting lots of new friends who all got on from many nationalities. At a restaurant one evening another group asked if we were a family which is how we ended up but without the disputes! Our skipper, Rita displayed wonderful leadership & sailing skills telling many interesting stories. Twice we has difficult dockings in strong crosswinds & other boats were messing it up big time but Rita nailed it both times & I was informed she received applause at Mykonos from the people on the dock. She also spent lot of time producing a video of our trip that she gave to us all. If your other CEO’s are half as good as her you have a very good team. Please note that you may only use my first name publically for this review, Peter!
Sail Greece: Santorini to Mykonos - D
Deborah • traveled in July, 2024
This was on my bucket list and it has exceeded my expectations,loved every minute of it and it was all down to our amazing skipper .
Greece Sailing Adventure: Cyclades Islands - L
Lynn • traveled in January, 2026
What a fabulous trip to Greece! Joy hosted such a fabulous itinerary with a great group of people. So memorable. From start to finish it was an amazing trip. She organized a wonderful itinerary for us, provided delicious Greek breakfast and lunches as well as organized nice restaurants for dinners. Every day was just so picturesque. I have beautiful memories hanging on my walls. She was so helpful with all points in the process from exchanging to Euros to recommending accommodations before and after trips. She held informative Zoom sessions prior to assist with any questions, allow our trip-mates meet and provide helpful suggestions with lodging and packing. I loved the trip so much I took another trip to Sicily Italy with her. If these places are on your bucket list, Joy will help you make the most memorable trips!
Sailing Adventure through the Saronic Gulf
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95 Sailing trips in Greece with 391 reviews
Compiled by
MelissaGreece travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Cyclades Luxury Sailing Adventure (Catamaran)
- Sailing Greece - Santorini to Mykonos
- Luxury Sailing & Archaeology adventure 8days
- Sailing the Ionian Islands
- Set sail from Zakynthos
- Southern Cyclades Sailing Cruise 2026
- Greece: Sail & Swim
- Sailing & Hiking the Dodecanese Islands
- Sail Greece: Mykonos to Santorini
Greece Sailing Adventure: Cyclades Islands
20 Reviews by TourRadar travelers“I've already gotten a few friends to use Intrepid as well. There are many groups to choose from and I've found you to be the best by far.”
Carmen, traveled in May
Your 54-56ft yacht connects 9 islands over 10 days, from Santorini's dramatic caldera to Mykonos' vibrant harbors. The journey includes secluded beaches like Paradisi and Gaidharos Bay, with basic sailing instruction throughout.
Duration 10 days Destinations Santorini, Ios, Oia, Amorgos, Katapola, Cyclades, Koufonisia, Iraklia, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,840+$128 local payments
Cyclades Luxury Sailing Adventure (Catamaran)
3 Reviews by TourRadar travelers“The views were unbeatable, and everything was smoothly run!”
Marley, traveled in July
The luxury catamaran departs Athens Marina for the Cyclades archipelago. The route includes Milos's volcanic formations, Sifnos's medieval Kastro, and Kythnos's thermal springs. Professional skipper guides 209-nautical-mile adventure over 8 days.
Duration 8 days Destinations Athens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos, Kythnos Age Range All Ages Welcome Operator Trails Beyond From
- US$2,850
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“He created a great camaraderie among those on the trip. He was infallible ;)”
Timothy, traveled in May
Your 57-ft yacht adventure spans from Santorini's caldera to Mykonos's windmills. The route connects islands like Folegandros and Sifnos, revealing hidden coves and remote beaches. Traditional harbors and local tavernas showcase spectacular Cyclades sailing.
Duration 8 days Destinations Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos Age Range Ages 16+ Operator G Adventures From $1,679
25% Off- US$1,259You save $420
Luxury Sailing & Archaeology adventure 8days
1 Review by TourRadar travelers“Hands down best trip ever! Danae and Costas were very gracious hosts and passionate about sharing a unique side of Greece.”
IreneMeyer, traveled in May
The Saronic Gulf stretches 102 nautical miles, offering UNESCO site visits alongside island wonders. Peaceful coves near Agkistri provide anchorage, while Methana's volcanic beaches offer swimming spots. Traditional ports from Aegina to Hydra dot the route.
Duration 8 days Destinations Athens, Agkistri, Corinth, Mycenae, Palaia Epidavros, Epidaurus, Nafplion, Methana, Poros, HydraSee all destinations Age Range Ages 8+ Operator Trails Beyond From
25% Off- US$3,224
The 25-passenger gulet awaits in Corfu's UNESCO Old Port for a trip costing around $1,100. Highlights include Sivota's Blue Lagoon, Antipaxos's Voutoumi beach, and Paxos's hidden coves. The 8-day voyage features snorkeling, beachfront taverna dinners, and Ionian Sea views.
Duration 8 days Destinations Corfu, Sivota, Parga, Antipaxos Island Age Range All Ages Welcome Operator Encounters Travel From
25% Off- US$995
A traditional gulet carries you from Zakynthos to iconic Greek destinations. The route includes Fiskardo's white pebble beaches, Meganisi's hidden coves, and the famous Shipwreck Beach. Seven nights at sea with ensuite cabins and authentic Greek cuisine.
Duration 8 days Destinations Zakynthos, Agia Efimia, Ithaca, Meganisi, Fiskardo Age Range All Ages Welcome Operator Encounters Travel From
25% Off- US$995
Southern Cyclades Sailing Cruise 2026
1 Review by TourRadar travelers“cozy tour that i would like to repeat next year.”
Igor, traveled in May
Duration 8 days Destinations Athens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos Age Range Ages 8+ Operator Running On Waves From
25% Off- US$4,903+$425 upfront costs
A traditional motorized vessel takes you through Greece's Saronic Gulf to six distinct islands. The itinerary features Aegina's Temple of Apollo, swimming in Poros' secluded bays, and walks through Hydra's car-free streets. Daily swim stops and fresh Greek cuisine included.
Duration 8 days Destinations Athens, Aegina, Poros, Ermioni, Spetses, Hydra Age Range Ages 18-32 Operator Topdeck From $2,539
10% Off- US$2,289You save $250
The Hanse 370 yacht Armida sails 26 nautical miles from Kos to Nisyros. The route includes Symi's cosmopolitan harbor and secluded Alimia bay. Professional crew guides through 120 nautical miles of Aegean waters over 7 adventure-filled days.
Duration 7 days Destinations Kos, Gyali Island, Nisyros Island, Tilos, Alimia, Chalki, Symi, Rhodes Age Range Ages 10+ Operator Trekking Hellas Rhodes From
10% Off- US$4,375
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“This was an amazing experience and Fotis was a fantastic skipper who had a wealth of knowledge about sailing and the islands we were sailing through.”
Justin, traveled in May
A modern yacht carries you from Mykonos through Greece's maritime treasures. The route includes Little Venice and the Church of Panagia Paraportiani, plus hidden gems in the Small Cyclades. Traditional Greek sailing meets secluded bay exploration.
Duration 8 days Destinations Mykonos, Syros, Naxos, Amorgos, Ios, Santorini Age Range Ages 15+ Operator Intrepid Travel From
10% Off- US$2,110+$117 local payments
What our customers ask about Sailing in Greece
What is the best time of year to go sailing in Greece?
Greece's sailing season peaks from May to September with each month offering distinct advantages. The Ionian Sea maintains gentle winds throughout summer while the Cyclades experiences stronger gusts during July and August. Most travelers find June and September offer the best combination: temperatures hover between 25-30°C with less crowded ports in popular stops like Santorini and Mykonos. A TourRadar traveler notes: "We went in June and we had the perfect balance of wind for sailing and calm seas for swimming."
What are the top destinations covered on Greek sailing itineraries?
Greek sailing routes typically focus on two main island groups. The Cyclades circuit includes Mykonos Santorini and Naxos featuring distinctive white architecture and significant archaeological sites like Ancient Delos. The Ionian journey covers Lefkada Kefalonia and Ithaca offering sheltered waters and historical landmarks including Odysseus's home in Vathi. A TourRadar traveler shared: "Exploring hidden coves in Milos and visiting the Blue Caves of Lefkada were highlights - each island offered something unique and special."
How many people typically share a sailing vessel?
Greek sailing tours maintain small group sizes for comfort and personalization. Standard vessels like the Lagoon 42 catamaran host 8-10 guests while larger traditional boats such as the Running On Waves accommodate slightly more passengers. One TourRadar traveler observed: "Having just 8 people on board created a perfect dynamic - we became like family by the end of the trip."
What's the typical budget needed beyond the tour price?
Daily expenses beyond the tour cost average 50-60 USD covering non-included meals (mainly dinners) optional activities and local transport. Port fees may add around 395 USD per person on certain tours. Popular destinations like Mykonos and Santorini command higher restaurant prices. A TourRadar traveler advises: "Plan for around 30-40 USD per dinner at local tavernas plus extra for activities like wine tastings or archaeological site visits."
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