Sailing Tours & Trips in Greek Islands
4.5 stars on(7,233 reviews)- Choose from 38 Greek Islands tours
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10 best sailing Greek Islands tours
Compiled by
MelissaGreek Islands travel expert at TourRadar
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Cyclades Luxury Sailing Adventure (Catamaran)
- Sailing the Greek Mediterranean
- Yoga Sailing in Greece - Ionian Sea
- Set sail from Zakynthos
- Mykonos Party at Sea
- Greece Paros Explorer: Superior Catamaran From Paros
- Greece Lefkada Explorer: Superior Catamaran From Lefkas, Lefkada
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“Very inclusive, puts everyone at ease and creates a great team environment.”
Tracey, traveled in June 2019
- Explore Mykonos and unwind on sandy beaches
- Sail to Naxos, visit ancient temples and groves
- Discover Syros' neo-classical architecture
Duration 8 days Destinations Mykonos, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini Age Range 15 to 99 year olds Operated in English Operator Intrepid Travel From $1,795
10% Off- US$1,615+$105 local paymentsYou save $180
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“Loved this sailing adventure and plan to do another one in the near future. Our group gelled well and we all had fun.”
Cynthia, traveled in August 2023
- Explore Mykonos by night on arrival day
- Discover hidden gems with flexible sailing
- Visit Homer's tomb and relax on Manganari beach
Duration 8 days Destinations Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini Age Range 18 to 99 year olds Operated in English Operator G Adventures From $1,479
10% Off- US$1,331You save $147
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“From phenomenal views to good food. The Santorini to Santorini gadventures experience was great.”
Rochelle, traveled in December 2022
- Join a welcome meeting on a sailing yacht
- Relax on Magganari beach in Ios
- Explore Mykonos and its iconic windmills
Duration 10 days Destinations Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros Age Range 16 to 70 year olds Operated in English Operator G Adventures From $1,999
10% Off- US$1,799You save $199
Cyclades Luxury Sailing Adventure (Catamaran)
3 Reviews by TourRadar travelers“It is impossible to express how much we loved our trip. This was a once in a lifetime trip for us.”
Marla, traveled in May 2024
- Embark on a boat tour at Cape Sounio
- Dive from the boat at Temple of Poseidon
- Explore the Venetian Fortress in Serifos
Duration 8 days Destinations Athens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos, Kythnos Age Range 4 to 88 year olds Operated in English, Spanish Operator Trails Beyond From
10% Off- US$2,507
Sailing the Greek Mediterranean
1 Review by TourRadar travelers“This sailing tour was quite possibly one of the most unique experiences of my life. I would highly recommend to anyone looking to sail around the Greek isles!”
Taylor, traveled in May 2024
- Shop for groceries and settle on your yacht
- Sail to Ermioni with swimming stops
- Cook and stargaze in a secluded bay
Duration 8 days Destinations Lavrion, Kea, Serifos, Milos, Sifnos Age Range 20 to 40 year olds Operated in English, German Operator sailwithus From
10% Off- US$730+$264 local payments
- Find your zen while sailing the Ionian
- Daily morning yoga in breathtaking locations
- Daily sailing and swim stops
Duration 8 days Destinations Lefkada, Ithaca, Sami, Fiskardo, Meganisi, Kalamos, Lefkas Age Range 18 to 80 year olds Operated in English Operator Med Sailing Holidays From
10% Off- US$1,999
- Zante, Agios Nikolaos, Agia Efimia, Ithaca, Meganisi, Fiskardo, Poros.
Duration 8 days Destinations Zakynthos, Agia Efimia, Ithaca, Meganisi, Fiskardo Age Range up to 99 year olds Operated in English Operator Encounters Travel From
10% Off- US$900
- Ancient Athens, Kea, Siros, the beautiful island of Mykonos, Kythnos
Duration 8 days Destinations Lavrion, Kea, Kythnos, Mykonos Age Range 18 to 35 year olds Operated in English Operator Encounters Travel From
10% Off- US$660
- Stroll through Paros' whitewashed chapels
- Watch the sunset from Antiparos town square
- Taste organic wine on a cliff in Sikinos
Duration 7 days Destinations Paros, Antiparos, Ios, Schoinousa, Ano Koufonisi Island, Naxos Age Range up to 65 year olds Operated in English Operator Yacht Getaways From $1,995
5% Off- US$1,895+$296 local paymentsYou save $99
- Start your sail from vibrant Lefkas Island
- Explore the caves at Foki Bay, Kefalonia
- Dine in charming Kioni, Ithaca
Duration 7 days Destinations Lefkas, Vathy, Ithaca, Agia Efimia, Fiskardo Age Range up to 65 year olds Operated in English Operator Yacht Getaways From $2,030
5% Off- US$1,929+$296 upfront costsYou save $101
