Sailing Tours & Trips in Aegean Islands
4.5 stars on(8,174 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
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Mykonos
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- Sailing the Greek Mediterranean
- Sailing & Hiking the Dodecanese Islands
- Southern Cyclades Sailing Cruise 2026
- Authentic Greece. Northern Cyclades Cruise 2025
- Mykonos Party at Sea
- Sailing Greece - Santorini to Santorini
Sailing Greece - Mykonos to Santorini
50 Reviews by TourRadar travelers“I felt the experience was good and the scenery spectacular.”
Tanya, 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
- NZ$2,199
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“it was a great way to see many of the islands and the skipper organized many extra activities for us.”
Barry, 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 $459
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
A 54-56ft sailing yacht takes you through Aegean waters from Santorini to pristine coves. The itinerary features swimming at Gaidharos Bay, visits to Amorgos' 11th-century Moni Hozoviotissis monastery, and hands-on sailing between islands. Share authentic maritime life with 11 fellow passengers.
Duration 10 days Destinations Santorini, Ios, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros Age Range 15 to 99 year olds Operator Intrepid Travel From $3,775
20% Off- NZ$3,020+$209 local paymentsYou save $755
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“Having an organized trip and itinerary that is well researched.”
Nicole, traveled in June
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 $2,770
15% Off- NZ$2,354+$190 local paymentsYou save $416
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
15% Off- NZ$1,389+$475 local payments
The Hanse 370 yacht Armida takes you through secluded bays and pristine coves of the Aegean. The 120-nautical-mile journey from Kos to Rhodes includes stops at Gyali's crystal waters and Symi's historic harbor. Professional crew guides you through the Dodecanese archipelago.
Duration 7 days Destinations Kos, Gyali Island, Nisyros Island, Tilos, Alimia, Chalki, Symi, Rhodes Age Range 10 to 80 year olds Operator Trekking Hellas Rhodes From
15% Off- NZ$6,946
Duration 8 days Destinations Athens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos Age Range 8 to 99 year olds Operator Running On Waves From
15% Off- NZ$8,164+$751 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
15% Off- NZ$6,280+$751 upfront costs
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 18 to 35 year olds Operator Encounters Travel From
15% Off- NZ$1,445
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
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
20% Off- NZ$2,639You save $659
What people love about Sailing Tours in Aegean Islands
- Sailing Greece - Mykonos to Santorini
Highly recommend doing a Sail Greece. It was a week packed full of activities, Islands and making new friends.
Had an amazing time, the tour was very well organized, the boat very comfortable for the 12 people that traveled in it. We met some wonderful people from around the world, we visited amazing places, our tour guide George was very nice and knowledgeable and always went the extra mile to organize everything perfectly for us. The experience of a lifetime!!
Greece Sailing Adventure: Cyclades Islands
- Sailing Greece - Santorini to Santorini
Surpassed my expectations! Had an amazing time and got shown the best of all the spots!
