Sailing Tours & Trips in Aegean Islands
4.5 stars on(8,464 reviews)- Choose from 21 Aegean Islands tours
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10 best sailing Aegean Islands tours
Compiled by
MelissaAegean Islands travel expert at TourRadar
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Mykonos
- Sailing the Greek Mediterranean
- Southern Cyclades Sailing Cruise 2026
- Authentic Greece. Northern Cyclades Cruise 2025
- Bodrum - North Dodecanese | Weekly Premium Blue Cruise
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Santorini to Santorini
- Sailing Greece - Mykonos to Mykonos
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“What an amazing trip! Itinerary was amazing. Yes, sailing and boat life is not for everybody, but with a bit of resilience all is doable.”
Anamaria, traveled in August
A modern yacht carries travelers from Mykonos's Little Venice to Thirasia's volcanic shores. The route includes hands-on sailing through the Small Cyclades, stops at Amorgos's ancient port of Katapola, and visits to Ios's protected Kolitzani Beach. The trip balances sailing adventures with island exploration.
Duration 8 days Destinations Mykonos, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini Age Range 15 to 99 year olds Operator Intrepid Travel From $2,905
25% Off- NZ$2,179+$192 local paymentsYou save $726
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“This was one of the most amazing trips I have ever been on, it is an active sailing trip.”
Heather, traveled in June
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 18 to 99 year olds Operator G Adventures From $2,299
25% Off- NZ$1,724You save $575
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“Our guide brought us to so many amazing places we wouldn't have known to go to on our own.”
Derek, traveled in August
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 16 to 70 year olds Operator G Adventures From $2,299
20% Off- NZ$1,839You save $460
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
The crystal waters of the Aegean stretch from Lavrion to Hydra and Spetses. Master sailing basics while visiting car-free islands and hidden bays. The trip includes professional instruction, yacht accommodation, and personalized route planning for optimal conditions.
Duration 8 days Destinations Lavrion, Kea, Serifos, Milos, Sifnos Age Range 20 to 40 year olds Operated in English, German Operator sailwithus From
20% Off- NZ$1,478+$480 local payments
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 8 to 99 year olds Operator Running On Waves From
20% Off- NZ$8,237+$758 upfront costs
A fully-equipped vessel with marble-finished cabins carries you through Aegean waters. Thermal springs in Loutra, underwater caves of Amorgos, and exclusive spots like the double beach of Kolona await. Kayaking and windsurfing equipment provided for daily water activities.
Duration 8 days Destinations Athens, Kea, Syros, Delos, Mykonos, Amorgos, Naxos, Kythnos Age Range 8 to 99 year olds Operated in English, German Operator Running On Waves From
20% Off- NZ$6,336+$758 upfront costs
Duration 8 days Destinations Bodrum, Kos, Leros, Patmos, Lipsi, Kalymnos Age Range 10 to 99 year olds Operator Barbaros Yachting From
20% Off- NZ$3,139+$403 local payments
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, Cyclades, Amorgos, Naxos, Syros, Mykonos Age Range 15 to 99 year olds Operator Intrepid Travel From $2,755
25% Off- NZ$2,066+$192 local paymentsYou save $689
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
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 16 to 70 year olds Operator G Adventures From $3,299
30% Off- NZ$2,309You save $990
Sailing Greece - Mykonos to Mykonos
44 Reviews by TourRadar travelers“The 2nd Sailing Trip with G was just outstanding!”
Dario, traveled in June
A state-of-the-art 57-ft yacht takes you through the Aegean's azure waters, from Mykonos' Little Venice to Folegandros' clifftop villages. The route passes through Santorini's volcanic caldera, with stops at Ios' Magganari Beach and Naxos' ancient Temple of Dimitra.
Duration 10 days Destinations Mykonos, Syros, Paros, Folegandros, Santorini, Ios, Naxos Age Range 16 to 70 year olds Operator G Adventures From $3,139
35% Off- NZ$2,040You save $1,099
What people love about Sailing Tours in Aegean Islands
- 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.
An open mind and adventurous spirit are needed for this trip. If you have that and love the sea, this is a trip of a lifetime. This isn't a luxury sailing trip, this is real sailing, with cramped accommodations. But you get to be outside, sailing and exploring the islands, eating the best meals, and swimming in beautiful private bays.
Sailing Greece - Santorini to Santorini
- Sailing Greece - Mykonos to Mykonos
This was such a fantastic tour and the BEST way to travel the Cyclades in Greece. The ship was comfortable and performed well, my guide (Phil) was constantly making sure the trip was both comfortable and exciting, and the itinerary was unbeatable. The only downside was that the trip didn't last long enough - no fault of G or Phil, just not enough time! I could spend a year sailing around those islands. 5/5 stars across the board.
