Sailing Tours & Trips in Aegean Islands
4.5 stars on(7,619 reviews)- Choose from 20 Aegean Islands tours
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10 best sailing Aegean Islands tours
Compiled by
MelissaAegean Islands travel expert at TourRadar
- Sail Greece: Mykonos to Santorini
- Greece Sailing Adventure: Cyclades Islands
- Sailing the Greek Mediterranean
- Mykonos Party at Sea
- Greece Paros Explorer: Superior Catamaran From Paros
- Authentic Greece. Northern Cyclades Cruise 2025
- Southern Cyclades Cruise 2025
- Sailing Greece - Santorini to Mykonos
- Sailing Greece - Mykonos to Mykonos
- Sail Greece: Santorini to Mykonos
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“We had an excellent professional friendly delightful experience of a life time...we will never forget.”
Maureen, traveled in May 2019
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 15 to 99 year olds Operator Intrepid Travel From $1,795
10% Off- US$1,615+$104 local paymentsYou save $180
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“Amazing Tour with an amazing skipper.”
Kaja, traveled in May 2019
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 15 to 99 year olds Operator Intrepid Travel From $2,455
15% Off- US$2,087+$114 local paymentsYou save $368
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 2024
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 20 to 40 year olds Operated in English, German Operator sailwithus From
15% Off- US$720+$260 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 18 to 35 year olds Operator Encounters Travel From
15% Off- US$660
Azure waters lead from Paros to Antiparos's cobbled walkways and Sikinos's terrace-lined hills. Hands-on sailing with an RYA Yacht Master awaits, while Koufonisia's pristine coves and Naxos's western coastline offer perfect windsurfing conditions. Stand-up paddleboards available for calm-water adventures.
Duration 7 days Destinations Paros, Antiparos, Ios, Schoinousa, Ano Koufonisi Island, Naxos Age Range up to 65 year olds Operator Yacht Getaways From
15% Off- US$2,155+$292 local payments
A fully-equipped vessel with marble-finished cabins carries you through Aegean waters. Thermal springs in Loutra, underwater caves of Amorgos, and exclusive spots like the double beach of Kolona await. Kayaking and windsurfing equipment provided for daily water activities.
Duration 8 days Destinations Athens, Kea, Syros, Delos, Mykonos, Amorgos, Naxos, Kythnos Age Range 8 to 99 year olds Operated in English, German Operator Running On Waves From
15% Off- US$2,233+$424 upfront costs
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 8 to 99 year olds Operated in English, German Operator Running On Waves From
15% Off- US$2,233+$424 upfront costs
Sailing Greece - Santorini to Mykonos
20 Reviews by TourRadar travelers“I think the trips are good value, guides are knowledgeable and helpful, and 15 people is for me an ideal group size.”
Heather, traveled in September 2018
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 16 to 70 year olds Operator G Adventures From $1,679
17% Off- US$1,394You save $285
Sailing Greece - Mykonos to Mykonos
44 Reviews by TourRadar travelers“This gAdventures trip was a real sailing experience in a fantastic scenery of the Aegean Sea.”
Hélène, traveled in October 2022
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 16 to 70 year olds Operator G Adventures From $2,199
17% Off- US$1,825You save $373
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 2019
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, Cyclades, Amorgos, Naxos, Syros, Mykonos Age Range 15 to 99 year olds Operator Intrepid Travel From $1,775
10% Off- US$1,597+$104 local paymentsYou save $178
What people love about Sailing Tours in Aegean Islands
- Sailing Greece - Mykonos to Mykonos
I have been late writing the review :) however it was a great trip! Well organized and full of fun! Reccomended
- Sailing Greece - Mykonos to Santorini
It was a very good experience to visit the islands of Greece by boat. The team was very nice and the leader very helful with everything.
- Sailing Greece - Santorini to Santorini
Took a tour with G Adventures and really loved the experience. I did the May 2017 Greece Sailing tour and found that the tour was a perfect mix of the best food, best beaches, variety of sightseeing, relaxing, sailing and exploring. We also had a good amount of freedom to explore the islands where we stopped. The group brought together some adventurous people! The other unique thing about this tour was that it was not touristy or a large crowd. We felt like a group of friends exploring the local culture. I would recommend it for anyone who really wants to soak in the culture of the locale and also not stress out about bookings, schedules, costs, language barriers, etc. It's priced very fairly for what is included. Wish you the best of travel experiences!