Mytilini Harbour, Lesbos
Vathy Bay, Samos
Chios Town Harbour
Armenistis Bay, Ikaria
Myrina, Lemnos
Taste ouzo at a traditional distillery in Plomari, Lesbos
Sample Samos’s sweet Muscat wine at a coastal winery
Explore the medieval Mastic Villages of southern Chios
Swim in Ikaria’s naturally warm mineral springs at Therma
Visit the volcanic Petrified Forest of Lesbos
Mastic Villages (Mesta and Pyrgi), Chios
Molyvos Castle, Lesbos
Pythagoreio and the Heraion, Samos (UNESCO)
Myrina Castle, Lemnos
Nas beach and the Temple of Artemis, Ikaria
Late May through early October is prime season, but the Aegean isn’t uniform: July and August bring the strongest meltemi winds and the biggest crowds in Mykonos and Santorini, while June and September offer calmer seas, warm water and thinner harbours. Quieter North Aegean islands such as Lesbos and Samos hold their charm well into October, when the Cyclades’ bars and beach clubs have already begun closing for the season.
The Aegean has no single gateway: Mykonos (JMK), Santorini (JTR), Rhodes (RHO) and Kos (KGS) all have their own airports with direct flights from major European cities in summer, while Athens International (ATH) connects year-round and works well as a starting point for a wider itinerary that spans several island groups in one trip.
It depends which group you’re in: sheltered bays with tavernas on the beach are typical of the Cyclades and Dodecanese, while the North Aegean islands offer bigger, more open anchorages such as Vathy Bay on Samos or Mytilini Harbour on Lesbos. A good skipper will build the itinerary around whichever wind and swell direction the meltemi is producing that week, since not every anchorage is equally sheltered from every angle.
Ten days is a realistic minimum to properly explore just one group, whether that’s the Cyclades or the Dodecanese, with time for weather days and unhurried stops. Combining two groups, say the Cyclades and the Dodecanese, or venturing further to the North Aegean islands, is possible but usually calls for two to three weeks given the sailing distances involved.
Most guests do best picking one region rather than trying to see everything. The Cyclades suit a first-time Aegean charter, with short hops between famous names and a lively social scene. The Dodecanese reward guests drawn to history and slightly warmer, calmer water, while the quieter North Aegean islands, Lesbos, Samos and Chios, suit those who have already done the well-known route and want fewer other yachts nearby.
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