Sailing Tours & Trips in Aegean Islands
4.6 stars on(9,180 reviews)- Choose from 26 Aegean Islands tours
- 150+ verified reviews from TourRadar travelers
- 24/7 customer support
10 best sailing Aegean Islands tours
Compiled by
MelissaAegean Islands travel expert at TourRadar
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Southern Cyclades Sailing Cruise 2026
- Journeys: Discover the Greek Islands National Geographic Journeys
- Mykonos Party at Sea
- Northern Cyclades Cruise 2026
- Sail Greece: Mykonos to Santorini (12 destinations)
- Sail & Hike Greece: Athens to Mykonos
- Sailing Greece - Santorini to Mykonos
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
The bluest Aegean waters carry you from Santorini to Mykonos on a sleek 54ft yacht. Sailing skills improve between Ios's pristine Manganari Beach and Amorgos's rugged coastline. Traditional ports in Koufonisia and sunsets from Syros's hilltop Ano Syros village highlight the journey.
Duration 8 days Destinations Santorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos Age Range Ages 15+ Operator Intrepid Travel From
- NZ$2,855+$204 local payments
Sailing Greece - Mykonos to Santorini
54 Reviews by TourRadar travelers“Great itinerary. Great crew/passengers and great skipper.”
Wayne, traveled in September
The modern 57-ft yacht sails crystal Aegean waters from Mykonos to Santorini. Stops include Syros's elegant square, Naxos's Temple of Dimitra, and Antiparos's fascinating caves. Fresh seafood awaits at local tavernas, while Santorini's white-washed villages offer spectacular sunset views.
Duration 8 days Destinations Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini Age Range Ages 18+ Operator G Adventures From
- NZ$2,479
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
The 57-ft yacht glides through Aegean waters, visiting eight distinct islands over 10 days. Highlights include snorkeling in secluded coves, Homer's tomb on Ios, and Venetian ruins in Paros. From Mykonos' iconic windmills to Sifnos' ceramic workshops, this voyage showcases authentic Greek maritime life at approx. $230 per day.
Duration 10 days Destinations Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros Age Range Ages 16+ Operator G Adventures From
- NZ$3,399
Southern Cyclades Sailing Cruise 2026
1 Review by TourRadar travelers“cozy tour that i would like to repeat next year.”
Igor, traveled in May
Duration 8 days Destinations Athens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos Age Range Ages 8+ Operator Running On Waves From
- NZ$8,754+$806 upfront costs
Duration 8 days Destinations Athens, Mykonos, Naxos, Delos, Cyclades, Akrotiri, Santorini Age Range Ages 12+ Operator National Geographic Journeys with G Adventures From
- NZ$5,679
From Laurium port, the Aegean Islands await, with stops at Makronisos for swimming and Vourkari village exploration. Lively nights unfold in Ermoupoly and Mykonos town. The journey includes 7 nights on gulet with daily brunches for ages 18-35.
Duration 8 days Destinations Lavrion, Kea, Kythnos, Mykonos Age Range Ages 18-35 Operator Encounters Travel From
- NZ$1,420
Duration 8 days Destinations Athens, Kea, Syros, Delos, Mykonos, Amorgos, Naxos, Kythnos Age Range Ages 8+ Operator Running On Waves From
- NZ$8,754+$806 upfront costs
Duration 8 days Destinations Mykonos, Syros, Naxos, Amorgos, Ios, Santorini Age Range Ages 15+ Operator Intrepid Travel From
- NZ$2,950+$204 local payments
Duration 8 days Destinations Lavrion, Kea, Kythnos, Serifos, Loutra, Syros, Delos, Mykonos Age Range Ages 15+ Operator Intrepid Travel From
- NZ$3,090+$204 local payments
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“The sailing was an incredible experience and the best way to see Greece in my opinion. I also met some phenomenal people who have now become travel friends.”
Leigh, traveled in May
The 57-ft luxury yacht sails for 8 days between Santorini and Mykonos. Folegandros offers cliff-side exploration, while Sifnos showcases ceramic workshops. Hidden coves provide perfect snorkeling spots, with beach time at Magganari on Ios and stunning sunsets over Hora's whitewashed buildings.
Duration 8 days Destinations Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos Age Range Ages 16+ Operator G Adventures From
- NZ$2,399
What people love about Sailing Tours in Aegean Islands
- Sail Greece: Santorini to Mykonos
We had a great time meeting lots of new friends who all got on from many nationalities. At a restaurant one evening another group asked if we were a family which is how we ended up but without the disputes! Our skipper, Rita displayed wonderful leadership & sailing skills telling many interesting stories. Twice we has difficult dockings in strong crosswinds & other boats were messing it up big time but Rita nailed it both times & I was informed she received applause at Mykonos from the people on the dock. She also spent lot of time producing a video of our trip that she gave to us all. If your other CEO’s are half as good as her you have a very good team. Please note that you may only use my first name publically for this review, Peter!
- Sailing Greece - Mykonos to Santorini
I'm not certain what is meant about transportation, there was no transfer from the airport to the meeting point. If it was meant the actual sailing, it was excellent.
- Sailing Greece - Santorini to Santorini
Surpassed my expectations! Had an amazing time and got shown the best of all the spots!