Sailing Tours & Trips in Greek Islands
4.5 stars on(7,357 reviews)- Choose from 41 Greek Islands tours
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10 best sailing Greek Islands tours
Compiled by
MelissaGreek Islands travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Sailing the Greek Mediterranean
- Cyclades Luxury Sailing Adventure (Catamaran)
- Yoga Sailing in Greece - Ionian Sea
- Set sail from Zakynthos
- Mykonos Party at Sea
- Greece Paros Explorer: Superior Catamaran From Paros
- Premier Gulet 18-39s: 4-Day Zakynthos to Lefkada
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“Amazing Tour with an amazing skipper.”
Kaja, traveled in May 2019
- Discover Santorini's black beaches
- Admire views of the Aegean Sea
- Stroll through stone laneways
Duration 10 days Destinations Santorini, Ios, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros Age Range 15 to 99 year olds Operated in English Operator Intrepid Travel From
- US$2,455+$114 local payments
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“Brilliant, lucky had great weather and spent lots of time swimming and visiting islands.”
JANE, traveled in October 2024
- 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
- US$1,479
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“The overall Adventure is totally worth it! Best part of this Tour was the outstanding leadership.”
Joan, traveled in May 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
- US$1,999
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
- US$717+$259 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 2023
- 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
- US$2,464
- 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
- US$1,965
- 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
- 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
- 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
- US$2,148+$291 local payments
- Meet your crew and set sail from Greece
- Swim in the Ionian Sea and dine onboard
- Explore Kefalonia and enjoy local flavors
Duration 4 days Destinations Zakynthos, Kefallonia, Lefkada, Athens Age Range 18 to 39 year olds Operated in English Operator Go Sail Greece From
- US$525+$43 local payments
