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
- Sailing Greece - Santorini to Mykonos
- Sail Greece: Santorini to Mykonos
- Southern Cyclades Sailing Cruise 2026
- Yoga Sailing in Greece - Ionian Sea
- Sailing & Hiking the Dodecanese Islands
- Journeys: Discover the Greek Islands National Geographic Journeys
- Greek Island Cruise
- Northern Cyclades Cruise 2026
- Sailing Greece - Santorini to Santorini
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, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, Schoinousa, Naxos, SyrosSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,555+$130 local payments
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
The Greek Islands stretch before you aboard a 57-ft yacht from Santorini to Mykonos. Folegandros's hidden coves and Antiparos caves reveal their secrets. Traditional harbors, beach landings, and evening moorings in picturesque Cyclades ports create lasting memories.
Duration 8 days Destinations Santorini, Folegandros, Sifnos, Ios, Antiparos, Paros, Naxos, Mykonos Age Range Ages 16+ Operator G Adventures From $1,879
30% Off- US$1,315You save $564
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
30% Off- US$1,715+$118 local payments
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
30% Off- US$4,903+$425 upfront costs
A Lagoon 42 catamaran takes you through the Greek Islands, revealing hidden gems like Papa Nicholas Cave and Tilemachos Beach. Seven distinct ports offer daily yoga, swimming, and paddleboarding opportunities. Traditional Greek hospitality shines from Sivota to Kalamos.
Duration 8 days Destinations Lefkada, Ithaca, Sami, Fiskardo, Meganisi, Kalamos, Lefkas Age Range Ages 18+ Operator Med Sailing Holidays From
30% Off- US$2,346
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 5 days Destinations Kos, Nisyros Island, Tilos, Symi, Rhodes Age Range Ages 10+ Operator Trekking Hellas Rhodes From
30% Off- US$3,690
Ferries connect Mykonos, Naxos, and Santorini across turquoise Aegean waters, with a boat trip to UNESCO-listed Delos revealing ancient temples of Apollo and Artemis. Seaside dining at a Myconian restaurant and Santorini's caldera trail walk offer views over volcanic Palea and Nea Kameni islands (ages 12+).
Duration 8 days Destinations Athens, Mykonos, Delos, Naxos, Santorini, Palea Kameni Island, Nea Kameni Island, Oia Age Range Ages 12+ Operator National Geographic Expeditions with G Adventures From $3,649
25% Off- US$2,737You save $912
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 Karystos, Panagia, Nea Styra, Marathon, Marmari Age Range Ages 16+ Operator Explore! From $1,930
9% Off- US$1,760You save $170
Duration 8 days Destinations Piraeus, Kea, Ioulida, Syros, Ermoupouli, Galissas, Delos, Mykonos, Amorgos, ChoraSee all destinations Age Range Ages 8+ Operator Running On Waves From
9% Off- US$4,903+$425 upfront costs
Sailing Greece - Santorini to Santorini
30 Reviews by TourRadar travelers“He was a sailern theater, plumper, weather man and always made sure we are having a wonderful time.”
Derya, traveled in February
Hidden coves and pristine beaches of the Greek Islands unfold aboard a 57-foot yacht. Magganari Beach, Mykonos' Little Venice, and secluded swimming spots near Naxos' Temple of Dimitra await. Expert skippers guide your maritime journey.
Duration 10 days Destinations Santorini, Ios, Naxos, Mykonos, Syros, Paros, Sifnos, Folegandros Age Range Ages 16+ Operator G Adventures From $2,349
40% Off- US$1,409You save $940
What people love about Sailing Tours in Greek Islands
- Greece Sailing Adventure: Cyclades Islands
Outstanding organization. Amazing visits to the islands, each unique. Daily very helpful briefings.with island info, and great links sent to us, highlighted and enhanced the odyssey. Skipper highly experienced, congenial, friendly and always ready to answer our questions. Flexibility with departure, according to our needs and the daily activities. Great recommendations for dining, museum visits, extra excursion options. As a native English speaker living in Germany I did luck out with a marvelous lively mix of native speakers on our boat. I celebrated my birthday with this energetic group. The trip surpassed my expectations. I highly recommend this trip.
- Southern Cyclades Sailing Cruise 2026
cozy tour that i would like to repeat next year
- Greek Island Cruise
Excellent cruise. I enjoyed it very much. Everything was as described. Including issues. It is an older type of boat. The cabins are small. I travelled as a solo traveller and was lucky not to have to share with someone else. This would have been cramped especially with someone I didn't know. My cabin was very hot at night with not a lot of air flow. But the upper decks were wonderful to enjoy the laid back cruising experience. Somewhere to curl up to read and then more food! 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. Very experienced tour guide and cook and captain. We all followed the guidelines given to us and very much appreciated the knowledge of history and politics that our guide shared all throughout the cruise. I have now purchased books to further my knowledge. And I'd now love to join one of the hiking and cruising tours. The swimming was just divine. The clarity of the water was like a swimming pool. Lovely temperature. Cute little villages to browse around and lay on the beaches. Just save your shopping bug for Athens! Transfers went well. I felt well taken care of and enjoyed it all immensely - including my fellow travellers who were mostly solo travellers, so we all were able to buddy up easily with each other. Great atmosphere as well.
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."