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 - Santorini to Santorini
- Dodecanese Sailing Explorer
- 8-Day Rhodes, Nanou Bay, Symi, Tilos & Chalki Gulet Escape
- 8-Day Greek Islands Gulet Adventure: Athens, Kea, Syros, Mykonos & Kythnos
- Mykonos Party at Sea
- Sailing Greece - Santorini to Mykonos
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Mykonos to Mykonos
Greece Sailing Adventure: Cyclades Islands
“He made this trip a fantastic sailing experience.”
Elliot, 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, Thera, Firostefani, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, SchoinousaSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,883+$123 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
- US$2,112+$112 local payments
Sailing Greece - Santorini to Santorini
“It was a great trip and Adam was a great Captain!”
Daryl, traveled in June
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
- US$2,549
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
- US$1,195
Duration 8 days Destinations Rhodes, Symi, Tilos, Chalki Age Range All Ages Welcome Operator STM Tours LLC From
- US$1,550
Duration 8 days Destinations Athens, Kea, Syros, Mykonos, Kythnos, Nisi Salamina Age Range All Ages Welcome Operator STM Tours LLC From
- US$1,046
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
- US$930
Sailing Greece - Santorini to Mykonos
“Sailing was the perfect way to see various greek islands without the hassle of changing accommodations.”
Amanda, traveled in June
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
- US$1,799
Sail Greece: Mykonos to Santorini
“I would definitely do another sailing trip with Intrepid especially if Rita was at the helm!”
Tracy, 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
- US$2,202+$112 local payments
Sailing Greece - Mykonos to Mykonos
“Great experience & perfect way to discover Islands of Greece. For sure, that was not my last sailing trip.”
Florían, traveled in May
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 Ages 16+ Operator G Adventures From
- US$2,499
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 - Santorini to Santorini
Our Captain Martin is superb.
- Sailing Greece - Santorini to Mykonos
Fantastic itinery, wonderful fellow travellers friendly skipper who taught those who wanted to some sailing