Sailing Tours & Trips in Cyclades Greece
4.5 stars on(7,181 reviews)- Choose from 22 Cyclades Greece tours
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10 best sailing Cyclades Greece tours
Compiled by
MelissaCyclades Greece travel expert at TourRadar
- Sail Greece: Mykonos to Santorini
- Greece Sailing Adventure: Cyclades Islands
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Cyclades Luxury Sailing Adventure (Catamaran)
- Sailing the Greek Mediterranean
- Greece Paros Explorer: Superior Catamaran From Paros
- Mykonos Party at Sea
- Yoga Retreat. Cyclades cruise 2025
- Southern Cyclades Cruise 2025
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“Trip was exactly what I expected and more.”
Terry, traveled in May 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+$104 local paymentsYou save $180
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 $2,455
15% Off- US$2,087+$114 local paymentsYou save $368
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“Captain Ciaran was the best!!”
David, traveled in July 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“Best holiday of my life. Nick really gave us a great love for sailing.”
Brian, 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“Trip was amazing and defiantly the trip of a lifetime. HIGHLY recommended.”
Kimberly, traveled in August 2022
- 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$2,469
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$719+$260 local payments
- 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 $1,964
5% Off- US$1,867+$291 local paymentsYou save $98
- 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
5% Off- US$660
- 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
5% Off- US$2,233+$424 upfront costs
- 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
5% Off- US$2,233+$424 upfront costs
