Sailing Tours & Trips in Greek Islands
Picture yourself in glittering Mykonos, on sandy beaches with blue water that licks your toes. Sail to Naxos to see old temples and olive groves. Discover the stunning neo-classical buildings in Syros, and enjoy fresh seafood in the lovely Small Cyclades. See the famous sunset from the dramatic caldera of Santorini, where white-washed buildings cling to cliffs. A dream come true.
10 best sailing Greek Islands tours
Compiled by
MelissaGreek Islands travel expert at TourRadar
- Greece Sailing Adventure: Cyclades Islands
- Sail Greece: Santorini to Mykonos
- Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Athens
- Southern Cyclades Sailing Cruise 2026
- Sailing & Hiking the Dodecanese Islands
- Greek Island Cruise
- Greek Cruise and Island Walking
- Athens to Istanbul Adventure
- Journeys: Discover the Greek Islands National Geographic Journeys
Greece Sailing Adventure: Cyclades Islands
20 Reviews by TourRadar travelers“He made this trip a fantastic sailing experience.”
Elliot, traveled in August
Nine islands reveal themselves aboard a 54-56ft yacht, with peaceful stops at Gaidharos Bay. Sailing basics come alive navigating from Santorini's Athinios Port through the Cyclades, featuring swim stops at Paradisi Beach and hands-on crewing opportunities.
Duration 10 days Destinations Santorini, Ios, Oia, Amorgos, Katapola, Cyclades, Koufonisia, Iraklia, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,840+$131 local payments
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
Crystal waters guide you from Santorini's caldera to Mykonos aboard a 56ft yacht. Manganari Beach, the untouched Small Cyclades, and charming fishing villages dot your route. Sailing basics unfold while passing Amorgos's dramatic cliffs and Naxos's golden shores.
Duration 8 days Destinations Santorini, Ios, Amorgos, Koufonisia, Iraklia, Naxos, Syros, Mykonos Age Range Ages 15+ Operator Intrepid Travel From
- US$2,015+$119 local payments
Sailing Greece - Mykonos to Santorini
54 Reviews by TourRadar travelers“Great itinerary. Great crew/passengers and great skipper.”
Wayne, traveled in September
Mykonos launches your adventure aboard a state-of-the-art 57-ft yacht, with stops at Manganari Beach on Ios and Antiparos' hidden coves. Turquoise waters lead to Naxos's microbreweries and Sifnos's ceramic workshops, culminating in Santorini's legendary sunset from Hora's cliffside.
Duration 8 days Destinations Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, Folegandros, Santorini Age Range Ages 18+ Operator G Adventures From $1,699
25% Off- US$1,274You save $425
Sailing Greece - Santorini to Athens
13 Reviews by TourRadar travelers“The islands and not at least the Greek food was amazing. I would definitely recommend this trip!”
Emilie, traveled in May
A state-of-the-art 57-ft yacht carries you from Santorini to Athens over 15 days. Master sailing alongside expert skippers while visiting Cyclades highlights like Antiparos's caves and Kea's stone lion. Secluded coves and Mykonos' Little Venice sunsets create perfect moments.
Duration 15 days Destinations Santorini, Folegandros, Ios, Kimolos, Sifnos, Antiparos, Paros, Naxos, Mykonos, SyrosSee all destinations Age Range Ages 16+ Operator G Adventures From $3,549
25% Off- US$2,662You save $887
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
25% Off- US$4,903+$425 upfront costs
The Hanse 370 yacht Armida carries you through the Greek archipelago. Professional crew charts course from Kos marina through crystal Gyali waters to Rhodes' historic harbor. The journey reveals secluded bays of Alimia and Seskli, covering 120 nautical miles of Aegean sailing over 7 days.
Duration 7 days Destinations Kos, Gyali Island, Nisyros Island, Tilos, Alimia, Chalki, Symi, Rhodes Age Range Ages 10+ Operator Trekking Hellas Rhodes From
25% Off- US$4,467
Greek Island Cruise
35 Reviews by TourRadar travelers“The food was great, wholesome, home cooked and tasty experience - both on board and the lovely, and well-priced, restaurants we went to in the evenings.”
Leonie, traveled in July
The historic MV Isidoros II caique weaves through Evia's hidden coves, offering daily swims in Porto Buffalo's secluded lagoon and snorkeling near Petali Islands. Captain Thanos leads through the Gulf of Evia's crystalline waters, before evening meals in Karystos and Marmari's waterfront tavernas.
Duration 8 days Destinations Athens, Rafina, Karystos, Panagia, Argyro, Euboea (Evia), Eretria, Nea Styra, Porto Lafia, Marmari Age Range Ages 16+ Operator Explore! From
25% Off- US$1,890
Greek Cruise and Island Walking
16 Reviews by TourRadar travelers“Great interaction with rest of the group.”
Peter, traveled in June
The traditional caique MV Isidoros II carries you through Petali Archipelago, former summer home of Greek royalty. Crystal waters invite swimming and snorkeling, while authentic ports like Marmari and Karystos await. Captain Thanos brings 20 years of local expertise.
Duration 8 days Destinations Athens, Rafina, Panagia, Zarakes, Eretria, Marmari, Mili, Karystos Age Range Ages 16+ Operator Explore! From
25% Off- US$1,780
The luxury yacht Emerald Azzurra, carrying just 100 passengers, sails from Piraeus through Milos's colored rock formations and Santorini's caldera views. The journey encompasses Delos's ancient ruins, Mykonos's iconic windmills, and Patmos's sacred monasteries.
Duration 8 days Destinations Piraeus, Milos, Santorini, Delos, Mykonos, Patmos, Kusadasi, Istanbul Age Range Ages 12+ Operator Emerald Cruises From $17,290
59% Off- US$7,090You save $10,200
Ferry travel connects Athens with Mykonos and the wider Cycladic islands. In Mykonos, the Church of Panagia Paraportiani and Little Venice's waterfront cafes make for good stops. A guided tour takes you to Delos, the UNESCO archaeological site, walking the Sacred Way past ancient stone lions and temples dedicated to Apollo and Artemis. Village-to-village hiking through Naxos countryside goes from Kouroi to Chalki, with tastings of local Kytro liquor and olives along the way. The route includes the Portara marble gateway from the 6th century BC.
Duration 8 days Destinations Athens, Mykonos, Naxos, Delos, Cyclades, Akrotiri, Santorini Age Range Ages 12+ Operator National Geographic Expeditions with G Adventures From
59% Off- US$3,399
What people love about Sailing Tours in Greek 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!
Short, but sweet. Sailing from island to island was very cool, much more fun than just ferry hopping. Because of the nature of sailing, the itinerary is very open, and you have the chance to see many places, where you would never go as a normal ferry using tourist, like hidden caves, or snorkeling spots near sunken WW2 planes. Our Skipper CEO Kristien did a great job at letting us choose what to do next and giving us the best possible experience. The Group I travelled with, even though very small, didn't have the best cohesion, so a lot of sub group split up. Luckily this is not the norm on GAdventuresw trips, but probably just bad luck. Maybe the age difference was too high. FYI: Yes, in the end you don't stop on Santorini, but the neighbor island Thirasia, this is because neither in the ferry port, or the old port, there is a possibility for sailing boats to dock. I think that was a good thing though, because this way we could see an additional island. In the morning a water taxi brought us to the ferry port, where busses already waited to bring people to Fira, so I had zero problems with transfer.
Sailing Greece - Mykonos to Santorini
- Sailing Greece - Santorini to Athens
All was perfect. Amazing skipper, nice teamwork with other skippers, good organization. Had an amazing time!
What our customers ask about Sailing Tours & Trips in Greek Islands
What is the best time of year to sail the Greek Islands?
The Greek Islands welcome sailors from May to October with July and August drawing the largest crowds. These peak months bring reliable winds and warm waters particularly in the Cyclades where conditions are right for swimming and water activities. As one TourRadar traveler noted: "The waters were warmer and the beaches spectacular the further south you go into summer." Many experienced travelers opt for May-June or September-October when the waters are still inviting but the ports are less crowded and prices tend to be lower.
What are the most popular sailing routes in the Greek Islands?
The Cyclades route stands out as a favorite taking sailors through Mykonos Santorini and Paros where ancient traditions meet modern island life. The Ionian Islands route from Zakynthos to Kefalonia offers protected waters and quiet coves while the Dodecanese chain lets travelers explore Rhodes and Kos. A TourRadar traveler shared: "Our skipper even led us to some spots where we could jump off the boat and swim to a cave snorkel over a wreck of a World War 1 German plane and enjoy random swims in the Mediterranean."
What meals are typically included on Greek Islands sailing tours?
Most boats serve either half-board or full-board meals with an onboard chef handling the cooking. Running On Waves serves three daily meals featuring Mediterranean dishes and local specialties while Med Sailing Holidays provides breakfast lunch and daytime snacks. Evening meals often happen at local tavernas in port. As one TourRadar traveler noted: "Our Chefs came from luxurious hotels and prepared amazing buffet meals with local Greek specialties." Some boats use a shared food kitty system where guests contribute about 50 USD weekly for basic supplies.
What type of accommodation can I expect on a sailing tour?
Boats typically provide double or twin cabins with shared bathrooms. Standard monohull yachts like those used by Intrepid Travel come with 2-3 double cabins 2 twin cabins and common bathroom facilities. Higher-end vessels such as the Benetti 52 in Mykonos offer private bathrooms and air conditioning. According to a TourRadar traveler: "While cabins are compact we spent most time on deck enjoying the views and only used cabins for sleeping."
How accessible is Wi-Fi during the sailing tour?
Internet access comes mainly during port stops rather than at sea. Travelers can connect at waterfront cafes restaurants and marinas such as Marina Alimos in Athens or Kos Marina. Land-based stays at properties like the Astro Palace Hotel in Santorini provide reliable connections. As one TourRadar traveler noted: "We actually enjoyed being disconnected while sailing and could easily catch up online during our evening port stops."
What kind of activities are available during island stops?
Each port brings new possibilities from exploring the Temple of Poseidon at Cape Sounion to swimming at Kolona Beach on Kythnos. Travelers can walk through traditional villages like Hora on Folegandros or taste local wines in Santorini. Evening activities range from sunset watching in Oia to dining at family tavernas. A TourRadar traveler shared: "Each island offered something unique - from hidden beaches in Milos to amazing local restaurants in Sifnos and nightlife in Mykonos."