Sailing Tours & Trips in Cyclades Greece
4.5 stars on(7,069 reviews)- Choose from 23 Cyclades Greece tours
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10 best sailing Cyclades Greece tours
Compiled by
MelissaCyclades Greece travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Sailing Greece - Mykonos to Santorini
- Sailing the Greek Mediterranean
- Cyclades Luxury Sailing Adventure (Catamaran)
- Greece Paros Explorer: Superior Catamaran From Paros
- Mykonos Party at Sea
- Yoga Retreat. Cyclades cruise 2025
- Southern Cyclades Cruise 2025
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“We got to see the less populated, smaller islands at just the very beginning of tourist season. There was an overall great balance between all the islands we visited.”
Elizabeth, 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 $2,455
- US$2,210+$118 local paymentsYou save $245
- Price per day
- $221
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“We had a great time on the boat. Made us feel very welcome and showed us all the relevant stuff.”
Lukas, 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
- US$1,616+$108 local paymentsYou save $179
- Price per day
- $202
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“The very best way to see the islands and avoid the crowds. Loved the boat family we created.”
Jacqueline, traveled in May 2023
- 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 $2,199
- US$1,539You save $659
- Price per day
- $154
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“Great people, swimming spots and got to experience a lot of different islands.”
Abby, 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
- US$1,331You save $147
- Price per day
- $166
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$746+$270 local payments
- Price per day
- $93
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
- US$2,562
- Price per day
- $320
- 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 $2,038
- US$1,937+$302 local paymentsYou save $101
- Price per day
- $277
- 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
- Price per day
- $83
- 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
- Price per day
- $279
- Explore the bustling port of Piraeus
- Discover Milos' colorful landscapes
- Climb Santorini's ancient caldera
Duration 8 days Destinations Athens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos Age Range 8 to 99 year olds Operated in English, German Operator Running On Waves - From
- US$2,233+$424 upfront costs
- Price per day
- $279
