Destination
Cyclades, Ionian & Dodecanese — Where Mythology Meets the Mediterranean
White-cube villages tumbling down volcanic cliffs. Tavernas where the octopus dries on a line in the sun. Over 6,000 islands — 227 inhabited — connected by sapphire water and the Meltemi wind. Greece is the original sailing paradise, and nothing else comes close to the feeling of dropping anchor in a new Greek harbor every night.
Best Season
May through October. The Meltemi wind blows strong (20-30 knots) from the north in July–August — exhilarating sailing but demanding. Shoulder months (May–June, September–October) offer 10–15 knot breezes, warm water, and thinner crowds.
Perfect For
Culture lovers, history buffs, foodies, and experienced sailors who want more wind. The Cyclades reward confident crews with some of the most dramatic landscapes in sailing. The Ionian is gentler — perfect for families and first-timers.
Must-Visit Spots
Sample Itinerary
Depart Lavrion marina southeast of Athens. A short 15-mile sail to Kea (Tzia), the closest Cycladic island. Anchor in Korissia Bay, hike to the ancient Lion of Kea.
Sail to Kythnos for a lunch stop at Kolona Beach — a double-sided sandbar. Continue to Serifos, a dramatic island with a hilltop Chora and the secluded bay of Psili Ammos.
Known as the culinary island of the Cyclades. Anchor at Vathy Bay, dine at a traditional taverna in Apollonia. Try mastelo — lamb slow-cooked in wine and dill.
Sail to Milos, the island of 70 beaches. Afternoon at Kleftiko (sea caves, snorkeling). Evening in Adamas harbor — waterfront dinner with views of the volcanic landscape.
One of the least touristed islands in the Cyclades. The clifftop Chora is breathtaking — winding alleys, bougainvillea, tavernas perched over a 200-meter drop. Anchor at Karavostasis.
Arrive at the caldera. Anchor off the volcanic island of Nea Kameni for a hot springs swim. Dinghy or tender to Fira. Sunset from the yacht is unforgettable.
Sail north to Paros. Stop in Naoussa for a final Greek lunch. Continue to Lavrion for checkout (or extend to Mykonos if time allows).
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