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: Mykonos to Santorini
- Sailing Greece - Santorini to Santorini
- Cyclades Luxury Sailing Adventure (Catamaran)
- 8-Day Sailing Escape in Greece – Zante to Kefalonia, Ithaca & Beyond
- Sailing the Ionian Islands
- Greek Island Cruise
- 8-Day Northern Ionian Island Gulet Adventure - Corfu, Sivota, Parga, Antipaxos, Paxos
- Family Greek Coast Caique Cruise
- Illyrian Cruise 2027
Greece Sailing Adventure: Cyclades Islands
“Amazing visits to the islands, each unique. The trip surpassed my expectations.”
Susan, traveled in May
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, Thera, Firostefani, Oia, Ios, Amorgos, Katapola, Koufonisia, Iraklia, SchoinousaSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,883+$123 local payments
Sail Greece: Mykonos to Santorini
“Booking was easy and the Intrepid booking staff were helpful and efficient. The trip itself was great.”
Amy, traveled in May
Crystal waters stretch from Mykonos's marina to Santorini's caldera aboard a 54-56ft yacht. Learn sailing basics while visiting Naxos's Portara gateway, secluded Koufonisia bays, and Ios's Valmas Beach. Seven nights aboard reveal six distinct Greek islands.
Duration 8 days Destinations Mykonos, Syros, Ermoupouli, Naxos, Chora, Koufonisia, Iraklia, Schoinousa, Amorgos, KatapolaSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- US$2,202+$112 local payments
Sailing Greece - Santorini to Santorini
“Best holiday of my life. Nick really gave us a great love for sailing.”
Brian, traveled in December
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
- US$2,549
Cyclades Luxury Sailing Adventure (Catamaran)
“The views were unbeatable, and everything was smoothly run!”
Marley, traveled in July
The Cyclades' hidden treasures unfold aboard a luxury catamaran, with stops at Kleftiko's pirate coves in Milos and Polyegos' crystal waters. Seven nights of sailing with a professional skipper reveal secluded swimming spots and traditional ports. Perfect for couples at approx. $320 per day.
Duration 8 days Destinations Athens, Sounio, Serifos, Kimolos, Polyaigos, Milos, Sifnos, Kythnos Age Range All Ages Welcome Operator Trails Beyond From
- US$2,782
Duration 8 days Destinations Zakynthos, Agia Efimia, Cephalonia, Lefkada, Meganisi, Ithaca, Atokos Island Age Range All Ages Welcome Operator STM Tours LLC From $1,644
17% off- US$1,364
Duration 8 days Destinations Corfu, Sivota, Parga, Antipaxos Island, Lakka, Paxi Age Range All Ages Welcome Operator Encounters Travel From
17% off- US$1,130
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, Marathon, Euboea (Evia), Karystos, Panagia, Nea Styra, Marmari Age Range Ages 16+ Operator Explore! From
17% off- US$1,900
Duration 8 days Destinations Corfu, Sivota, Parga, Antipaxos Island, Lakka Age Range All Ages Welcome Operator STM Tours LLC From $1,756
17% off- US$1,457
Family Greek Coast Caique Cruise
“The water was so clear we could see so many fish.”
Katherine, traveled in August
The traditional MV Isidoros II with Captain Thanos shows you Evia's azure waters. Petali archipelago and Porto Buffalo offer prime snorkeling spots. The route from Karystos to Panagia Bay includes deck sleeping under stars and crystal-clear cove swimming.
Duration 8 days Destinations Athens, Rafina, Euboea (Evia), Karystos, Panagia, Eretria, Nea Styra, Marmari Age Range Ages 7+ Operator Explore! From
17% off- US$1,970
Duration 8 days Destinations Corfu, Saranda, Lefkas, Zakynthos, Cephalonia, Paxi, Antipaxos Island Age Range Ages 8+ Operator Running On Waves From
17% off- US$4,498+$442 upfront costs
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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!
It is impossible to express how much we loved our trip. By the end Mike and Andreas were like family. We stayed in Greece a week after and I got great advice on where we should go. This was a once in a lifetime trip for us. We saved up for our 25th anniversary and we made the right choice. Big thanks to the guys and Danae.
Cyclades Luxury Sailing Adventure (Catamaran)
Our trip with Thanos was out of this world. The itinerary changed due to weather conditions from day to day ensuring smooth sailing. The coves for swimming were so beautiful and clear. George the onboard chef made some of the most tasty local dishes which everyone on board thoroughly enjoyed. Thanos our guide was such a lovely person who provided so much information and took the group on walks to visit ancient Greek sites. We learnt so much on our 8 day tour. The transportation to and from the cruise was very well organised. We ate in excellent tavernas and restaurants each night and local wine was very nice. Thank you to Vangelas (sorry for the spelling) for being such a great captain of our vessel. I could not recommend this cruise more highly.
Greek Island Cruise
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."