Sailing Tours & Trips in Aegean Islands
Picture sailing between Greek islands in the Aegean, waking up in different harbors. Sailing trips mean living aboard catamarans or monohulls, visiting islands tour boats skip, and swimming straight from the boat. Could be Cyclades (Mykonos, Paros, Naxos), Dodecanese (Rhodes, Kos), or Sporades. Sail during days, anchor in secluded bays, hit island towns for evenings. It's active but relaxed, with stunning scenery constantly.
10 best sailing Aegean Islands tours
Compiled by
MelissaAegean Islands travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Mykonos
- 6-Day Tour Athens & Santorini Island to Discover Greece's Charm
- The Santorini Adventure: Volcanoes, Villages & Hidden Gems
- Athens, Naxos & Santorini Sunset Cruise - Premium
- Greek Islands Explorer with Santorini Sunset Cruise - Premium
- Greece Culture History Sights with Santorini Catamaran tour
- Mykonos - Santorini 7 days
Greece Sailing Adventure: Cyclades Islands
21 Reviews by TourRadar travelers“Lots of time spent on the boat, beautiful swimming spots and a great way to spend a short time at lots of islands.”
Shannah, traveled in August
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, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From $2,564
24% Off- US$1,955+$125 local paymentsYou save $609
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 $1,712
19% Off- US$1,393+$114 local paymentsYou save $319
Sailing Greece - Mykonos to Santorini
54 Reviews by TourRadar travelers“I enjoyed getting the full sailing experience while Greek island jumping. It was a life changing experience.”
Ernie, traveled in July
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 $1,849
25% Off- US$1,387You save $462
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“He created a great camaraderie among those on the trip. He was infallible ;)”
Timothy, 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 $1,849
30% Off- US$1,294You save $555
6-Day Tour Athens & Santorini Island to Discover Greece's Charm
19 Reviews by TourRadar travelers“Hotel accommodations in both Athens and Santorini were awesome, easy access to everything.”
Geetha, traveled in December
Duration 6 days Destinations Athens, Santorini, Nea Kameni Island, Oia, Emporios, Perissa Age Range Ages 1-30 Operator Private Tours Greece From $2,341
25% Off- US$1,755You save $585
Athens, Naxos & Santorini Sunset Cruise - Premium
16 Reviews by TourRadar travelers“From the moment we landed in Athens everything ran like a swiss watch. All of the included hotels and activities were excellent.”
Nicholas, traveled in April
Duration 6 days Destinations Athens, Naxos, Santorini Age Range All Ages Welcome Operator Travel Zone From $1,919
15% Off- US$1,631You save $288
Greek Islands Explorer with Santorini Sunset Cruise - Premium
5 Reviews by TourRadar travelers“From the moment we landed till our departing flight took off, we were well taken care of. Wonderful, friendly, hard-working crew.”
Christy, traveled in August
Duration 9 days Destinations Athens, Syros, Mykonos, Santorini Age Range All Ages Welcome Operator Travel Zone From $3,248
15% Off- US$2,760You save $487
Greece Culture History Sights with Santorini Catamaran tour
2 Reviews by TourRadar travelers“The excursions were perfect. Everything was so smooth.”
Laura, traveled in June
Duration 7 days Destinations Athens, Santorini, Oia Age Range All Ages Welcome Operator Wanderful Holidays LLC From $1,599
5% Off- US$1,519You save $80
Duration 7 days Destinations Mykonos, Nisí Ríneia, Delos, Santorini, Oia Age Range Ages 18+ Operator Oxygen Tours From
5% Off- US$1,014
What people love about Sailing Tours in Aegean Islands
- Greece Sailing Adventure: Cyclades Islands
Did the 10 day sailing trip around greece! Had an amazing time. Lots of time spent on the boat, beautiful swimming spots and a great way to spend a short time at lots of islands. Spent most of the day out on the water and afternoon/nights exploring different greek islands. We had the most amazing skippers (George and Orestis). They mad the trip so fun and we’re full of information about Greece and the history. Definitely recommend this trip! Best skippers ever!
Short, but sweet. Sailing from island to island was very cool, much more fun than just ferry hopping. Because of the nature of sailing, the itinerary is very open, and you have the chance to see many places, where you would never go as a normal ferry using tourist, like hidden caves, or snorkeling spots near sunken WW2 planes. Our Skipper CEO Kristien did a great job at letting us choose what to do next and giving us the best possible experience. The Group I travelled with, even though very small, didn't have the best cohesion, so a lot of sub group split up. Luckily this is not the norm on GAdventuresw trips, but probably just bad luck. Maybe the age difference was too high. FYI: Yes, in the end you don't stop on Santorini, but the neighbor island Thirasia, this is because neither in the ferry port, or the old port, there is a possibility for sailing boats to dock. I think that was a good thing though, because this way we could see an additional island. In the morning a water taxi brought us to the ferry port, where busses already waited to bring people to Fira, so I had zero problems with transfer.
Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Mykonos
Max was an amazing Skipper and went to great lengths to ensure we all had an amazing experience. I highly recommend this trip and will definitely be coming back for future adventures.
