Sailing Tours & Trips in Aegean Islands
4.6 stars on(8,813 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 - Santorini to Santorini
- Sailing Greece - Santorini to Mykonos
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Mykonos to Santorini
- Sailing & Hiking the Dodecanese Islands
- Southern Cyclades Sailing Cruise 2026
- Sailing the Greek Mediterranean
- Mykonos Party at Sea
- Southern Cyclades Cruise 2025
- Sailing Greece - Mykonos to Mykonos
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“The overall Adventure is totally worth it! Best part of this Tour was the outstanding leadership.”
Joan, traveled in May
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 $3,339
25% Off- NZ$2,504You save $835
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“We had a great experience sailing with G Adventures. Highly recommend!”
Christina, 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 $2,359
25% Off- NZ$1,769You save $590
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“Varied and interesting itinerary. Got the whole group to bond together really well.”
Stephen, 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 Ages 15+ Operator Intrepid Travel From $3,760
20% Off- NZ$3,008+$217 local paymentsYou save $752
Sail Greece: Mykonos to Santorini
15 Reviews by TourRadar travelers“Booking was easy and the Intrepid booking staff were helpful and efficient. The trip itself was great.”
Amy, 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, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini Age Range Ages 15+ Operator Intrepid Travel From $2,845
20% Off- NZ$2,276+$198 local paymentsYou save $569
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
20% Off- NZ$7,212
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
20% Off- NZ$8,476+$780 upfront costs
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 Ages 20-40 Operated in English, German Operator sailwithus From
20% Off- NZ$1,521+$494 local payments
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
20% Off- NZ$1,420
Waters stretch from Piraeus to Milos' volcanic coastline and Folegandros' cliff-top towns. Santorini's caldera reveals itself by day, with sunset views from Fira at 220 meters above sea level. Modern amenities complement outside access in each cabin.
Duration 8 days Destinations Athens, Milos, Folegandros, Santorini, Astypalaia, Ios, Serifos Age Range Ages 8+ Operated in English, German Operator Running On Waves From
20% Off- NZ$6,520+$780 upfront costs
Sailing Greece - Mykonos to Mykonos
44 Reviews by TourRadar travelers“Overall great experience and you can expect us as future G adventure guests!”
Max, 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 $3,139
40% Off- NZ$1,883You save $1,256
What people love about Sailing Tours in Aegean Islands
- Sailing Greece - Mykonos to Santorini
I'm not certain what is meant about transportation, there was no transfer from the airport to the meeting point. If it was meant the actual sailing, it was excellent.
- Greece Sailing Adventure: Cyclades Islands
Great way to see and experience the cyclades.
- Southern Cyclades Sailing Cruise 2026
cozy tour that i would like to repeat next year