Sailing Tours & Trips in Greek Islands

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."