Sailing Tours & Trips in Greek Islands
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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 the Greek Mediterranean
- Cyclades Luxury Sailing Adventure (Catamaran)
- Set sail from Zakynthos
- Sailing & Hiking the Dodecanese Islands
- Bodrum and the Greek Islands
- Mykonos Party at Sea
- Premier Gulet 18-39s: 4-Day Zakynthos to Lefkada
- Sailing Greece - Santorini to Santorini
Greece Sailing Adventure: Cyclades Islands
18 Reviews by TourRadar travelers“I've already gotten a few friends to use Intrepid as well. There are many groups to choose from and I've found you to be the best by far.”
Carmen, 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, Ios, Amorgos, Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros Age Range 15 to 99 year olds Operator Intrepid Travel From
- US$2,555+$119 local payments
Sail Greece: Mykonos to Santorini
14 Reviews by TourRadar travelers“I would definitely do another sailing trip with Intrepid especially if Rita was at the helm!”
Tracy, 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, Naxos, Syros, Cyclades, Amorgos, Ios, Santorini Age Range 15 to 99 year olds Operator Intrepid Travel From $1,870
25% Off- US$1,402+$108 local paymentsYou save $468
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 Greek Islands await as you sail from Lavrion. Cast anchor at car-free Hydra, take refreshing dips in Kea's secluded bays, and savor local cuisine in Poros' traditional tavernas. Expert instruction and flexible route planning enhance your maritime adventure.
Duration 8 days Destinations Lavrion, Kea, Serifos, Milos, Sifnos Age Range 20 to 40 year olds Operated in English, German Operator sailwithus From
25% Off- US$750+$271 local payments
Cyclades Luxury Sailing Adventure (Catamaran)
3 Reviews by TourRadar travelers“Trip was amazing and defiantly the trip of a lifetime. HIGHLY recommended.”
Kimberly, traveled in August
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 4 to 88 year olds Operated in English, Spanish Operator Trails Beyond From
25% Off- US$2,577
The Ionian Sea beckons aboard a traditional gulet, featuring Zakynthos's Shipwreck Beach and Meganisi's hidden coves. Agia Efimia's charming harbor and Fiskardo's crystal waters await. This 8-day sailing adventure includes seven nights in ensuite cabins, with daily swims and coastal cruising.
Duration 8 days Destinations Zakynthos, Agia Efimia, Ithaca, Meganisi, Fiskardo Age Range up to 99 year olds Operator Encounters Travel From
25% Off- US$980
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 10 to 80 year olds Operator Trekking Hellas Rhodes From
25% Off- US$3,969
A traditional gulet takes you to Kalymnos's hidden coves and Lipsi's Platis Giolos beach. Secluded bays like Akvaryum offer perfect swimming and snorkeling spots. Seven nights of sailing connect authentic island ports.
Duration 8 days Destinations Bodrum, Kos, Pserimos, Leros, Patmos, Lipsi, Kalymnos Age Range 12 to 99 year olds Operator Fez Travel From
25% Off- US$2,125
The route from Laurium to Mykonos unfolds aboard a traditional gulet. Kea's Vourkari village, DJ parties in Ermoupoly harbor, and Mykonos' famous nightlife create unforgettable memories. Daily swim stops at Rhenia island and Kolona beach complete the journey.
Duration 8 days Destinations Lavrion, Kea, Kythnos, Mykonos Age Range 18 to 35 year olds Operator Encounters Travel From
25% Off- US$660
A traditional gulet carries you from Zakynthos to Lefkada through the Greek Islands. Kefalonia's authentic Agia Effimia port, secluded swimming coves, and Nydri's local markets await. Onboard accommodation, traditional Greek meals, and an optional Melissani Cave excursion enhance your journey.
Duration 4 days Destinations Zakynthos, Kefallonia, Lefkada, Athens Age Range 18 to 39 year olds Operator Go Sail Greece From
25% Off- US$541+$45 local payments
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
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 16 to 70 year olds Operator G Adventures From
25% Off- US$1,999
What people love about Sailing Tours in Greek Islands
- Greece Sailing Adventure: Cyclades Islands
captain of Intrepid Sailboat was incredible
- Cyclades Luxury Sailing Adventure (Catamaran)
It was an awesome experience! Having done something similar in Croatia, we were hoping this tour would have more planned excursions at each island stop (or at some of them; eg a walk to a historic site or bike rides at a given island etc), and instead the structure was that we’d get somewhere and then be free to sunbathe, wander the small town, get food on our own. Also great, but much more oriented to a very laid back, nearly zero activity sort of vacation. The crew was amazing, the boat was great, the views were unbeatable, and everything was smoothly run!
- 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!
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."