Sailing Tours & Trips in Aegean Islands
4.5 stars on(7,360 reviews)- Choose from 20 Aegean Islands tours
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10 best sailing Aegean Islands tours
Compiled by
MelissaAegean Islands travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Sailing the Greek Mediterranean
- Mykonos Party at Sea
- Greece Paros Explorer: Superior Catamaran From Paros
- Yoga Retreat. Cyclades cruise 2025
- Aegean Cruise 2025
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Mykonos to Mykonos
Greece Sailing Adventure: Cyclades Islands
18 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 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“He was a sailern theater, plumper, weather man and always made sure we are having a wonderful time.”
Derya, traveled in February 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$720+$260 local payments
- 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$2,155+$292 local payments
- Explore Piraeus and its vibrant harbors
- Discover Syros' blend of Cycladic and Venetian architecture
- Experience yoga sessions themed by natural elements
Duration 8 days Destinations Athens, Syros, Delos, Mykonos, Paros, Naxos, Icaria, Andros Age Range 8 to 99 year olds Operated in English Operator Running On Waves From
- US$2,233+$424 upfront costs
- Explore the bustling port of Piraeus
- Stroll through Ermoupolis' colorful streets
- Discover the sacred island of Delos
Duration 8 days Destinations Athens, Syros, Delos, Mykonos, Patmos, Kos, Santorini, Milos Age Range 8 to 99 year olds Operated in English, German Operator Running On Waves From
- US$2,233+$424 upfront costs
Sail Greece: Santorini to Mykonos
1 Review by TourRadar travelers“We had a great time meeting lots of new friends who all got on from many nationalities. Without the disputes!”
Peter, traveled in September 2019
- Enjoy the nightlife of Mykonos
- Sail the Cyclades
- Explore the mythology and history of Naxos
Duration 8 days Destinations Santorini, Ios, Cyclades, Amorgos, Naxos, Syros, Mykonos Age Range 15 to 99 year olds Operated in English Operator Intrepid Travel From
- US$1,775+$104 local payments
Sailing Greece - Mykonos to Mykonos
44 Reviews by TourRadar travelers“Awesome group, great skipper, beautiful spots discovered and filled with gratitude.”
Lynne, traveled in June 2022
- Join a welcome meeting on a yacht in Mykonos
- Explore markets and Venetian ruins in Syros and Paros
- Sail through Santorini's caldera and visit clifftop villages
Duration 10 days Destinations Mykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos Age Range 16 to 70 year olds Operated in English Operator G Adventures From
- US$1,999
