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 Santorini
- Sailing & Hiking the Dodecanese Islands
- Dodecanese Sailing Explorer
- 8-Day Rhodes, Nanou Bay, Symi, Tilos & Chalki Gulet Escape
- 8-Day Greek Islands Gulet Adventure: Athens, Kea, Syros, Mykonos & Kythnos
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Santorini to Mykonos
Greece Sailing Adventure: Cyclades Islands
“Amazing Tour with an amazing skipper.”
Kaja, 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, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,440+$128 local payments
Sail Greece: Santorini to Mykonos
“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 $2,102
28% Off- US$1,507+$116 local payments
Sailing Greece - Mykonos to Santorini
“Brilliant, lucky had great weather and spent lots of time swimming and visiting islands.”
JANE, traveled in October
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, Syros, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini, Thirasia Age Range Ages 18+ Operator G Adventures From
28% Off- US$1,749
Sailing Greece - Santorini to Santorini
“Wonderful trip with wonderful crew!”
Sarah, traveled in July
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 $2,499
25% Off- US$1,874
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 5 days Destinations Kos, Nisyros Island, Tilos, Symi, Rhodes Age Range Ages 10+ Operator Trekking Hellas Rhodes From
25% Off- US$3,639
A classic wooden gulet sails the southern Aegean for 8 days, stopping at hidden bays like Akrogiali Bay on Tilos and Kalithea's thermal spring coves near Rhodes. Overnight stays at ports include Symi and Panormitis, with swimming breaks at St. George Bay against cliff backdrops and sleeping under stars.
Duration 8 days Destinations Rhodes, Symi, Tilos, Chalki Age Range All Ages Welcome Operator Encounters Travel From
25% Off- US$1,195
Duration 8 days Destinations Rhodes, Symi, Tilos, Chalki Age Range All Ages Welcome Operator STM Tours LLC From $1,609
20% Off- US$1,287
Duration 8 days Destinations Athens, Kea, Syros, Mykonos, Kythnos, Nisi Salamina Age Range All Ages Welcome Operator STM Tours LLC From $1,086
20% Off- US$869
Sail Greece: Mykonos to Santorini
“This was an amazing experience and Fotis was a fantastic skipper who had a wealth of knowledge about sailing and the islands we were sailing through.”
Justin, traveled in May
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, Syros, Ermoupouli, Naxos, Chora, Koufonisia, Iraklia, Schoinousa, Amorgos, KatapolaSee all destinations Age Range Ages 15+ Operator Intrepid Travel From $2,192
14% Off- US$1,881+$116 local payments
Sailing Greece - Santorini to Mykonos
“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, Thirasia, Syros, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Mykonos Age Range Ages 16+ Operator G Adventures From
14% Off- US$1,679
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!
- Sailing Greece - Mykonos to Santorini
It was a fabulous yachting tour of the Greek Islands. I'll be recommending this to my friends.
- Sailing Greece - Santorini to Santorini
Excellent tour, great skipper, Marios and great group participation. Though travelling alone, I never felt left out. Our skipper / guide did everything to make the tour a joy !