Sailing Tours & Trips 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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Amazing captain. He made this trip a fantastic sailing experience
Greece Sailing Adventure: Cyclades IslandsWe 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 MykonosSuperb trip with fun hilarious skipper. Good group. Lots of nice islands and swim stops. One day with strong winds. Strong winds can happen in cyclades July and August, so if you get seasick easily avoid these months. Of the year but definitely do the trip.
Sailing Greece - Santorini to Santorini
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10 best Sailing Greece tour packages
Compiled by
MelissaGreece travel expert at TourRadar
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Greece Sailing Adventure: Cyclades Islands
“The actual trip was amazing. You have to allow 2 days for adjusting to boat life.”
Fiona, traveled in September
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, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From $2,848
19% Off- US$2,304+$129 local payments
Sail Greece: Santorini to Mykonos
“We had a great time meeting lots of new friends who all got on from many nationalities. Without the disputes!”
Peter, traveled in September
The modern 56ft yacht carries you along Greece's most scenic routes. Highlights include Santorini's Red Beach, Ios's Manganari Beach, and Naxos's ancient temples. Seven nights of authentic maritime life guided by skilled skippers.
Duration 8 days Destinations Santorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos Age Range Ages 15+ Operator Intrepid Travel From $2,102
28% Off- US$1,507+$117 local payments
Sailing Greece - Santorini to Santorini
“He was a sailern theater, plumper, weather man and always made sure we are having a wonderful time.”
Derya, traveled in February
The modern 57-foot yacht reveals secluded bays and ancient harbors throughout Greek waters. Stops include Magganari Beach on Ios, Mykonos' Little Venice, and Naxos' Temple of Dimitra. Rated 4.5/5 by previous travelers.
Duration 10 days Destinations Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros Age Range Ages 16+ Operator G Adventures From $2,599
40% Off- US$1,559
Sailing Greece - Santorini to Mykonos
“Fantastic itinery, wonderful fellow travellers friendly skipper”
Hardstyle, traveled in August
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, Thirasia, Syros, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Mykonos Age Range Ages 16+ Operator G Adventures From $1,849
30% Off- US$1,294
Cyclades Luxury Sailing Adventure (Catamaran)
“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
30% Off- US$2,897
Luxury Sailing & Archaeology adventure 8days
“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
30% Off- US$3,225
Duration 8 days Destinations Zakynthos, Agia Efimia, Cephalonia, Lefkada, Meganisi, Ithaca, Atokos Island Age Range All Ages Welcome Operator STM Tours LLC From $1,519
20% Off- US$1,215
What our customers ask about Sailing Tours & Trips 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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