Sailing Tours & Trips in Aegean Islands
4.6 stars on(9,532 reviews)- Choose from 22 Aegean Islands tours
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10 best sailing Aegean Islands tours
Compiled by
MelissaAegean Islands travel expert at TourRadar
- Sail Greece: Santorini to Mykonos
- Sail Greece: Mykonos to Santorini
- Sailing Greece - Santorini to Mykonos
- Southern Cyclades Sailing Cruise 2026
- Sailing & Hiking the Dodecanese Islands
- Northern Cyclades Cruise 2026
- Mykonos Party at Sea
- Sailing Greece - Santorini to Santorini
- Sailing Greece - Mykonos to Mykonos
- Sail Greece: Skiathos, Skopelos & Alonnisos
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
- NZ$2,855+$202 local payments
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“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, Naxos, Amorgos, Ios, Santorini Age Range Ages 15+ Operator Intrepid Travel From
- NZ$2,950+$202 local payments
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 Ages 16+ Operator G Adventures From $2,479
10% Off- NZ$2,231You save $248
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 Ages 8+ Operator Running On Waves From
10% Off- NZ$8,672+$798 upfront costs
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 Ages 10+ Operator Trekking Hellas Rhodes From
10% Off- NZ$7,570
Duration 8 days Destinations Athens, Kea, Syros, Delos, Mykonos, Amorgos, Naxos, Kythnos Age Range Ages 8+ Operator Running On Waves From
10% Off- NZ$8,672+$798 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 Ages 18-35 Operator Encounters Travel From
10% Off- NZ$1,420
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“Excellent tour, great skipper, Marios and great group participation. Though travelling alone, I never felt left out.”
Liam, 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 $3,499
15% Off- NZ$2,974You save $525
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 Ages 16+ Operator G Adventures From $3,779
30% Off- NZ$2,645You save $1,134
Duration 8 days Destinations Skiathos, Skopelos, Alonnisos Age Range Ages 15+ Operator Intrepid Travel From
30% Off- NZ$5,335
What people love about Sailing Tours in Aegean Islands
- Sail Greece: Mykonos to Santorini
Fantastic trip! Highly recommend
- Sailing Greece - Santorini to Santorini
Surpassed my expectations! Had an amazing time and got shown the best of all the spots!
- Southern Cyclades Sailing Cruise 2026
cozy tour that i would like to repeat next year