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6,000 islands. A lifetime of sailing.

Greece has more islands than most people will ever count — around 6,000 in total, 227 of them inhabited. This gives you the rare luxury of sailing for weeks without repeating a single anchorage. The three main sailing regions each have a distinct character: the Ionian in the west is greener and less windy, perfect for relaxed family cruising; the Cyclades in the central Aegean deliver dramatic landscapes and the legendary meltemi summer wind; the Dodecanese in the southeast blend Greek culture with echoes of Italian architecture and frontier sailing to Turkey.

The Cyclades — Mykonos, Santorini, Paros, Naxos, Syros — are the most iconic. The meltemi blows reliably from the north throughout summer, creating fast, exhilarating sailing downwind but challenging conditions when heading north. A skipper who knows the local acceleration zones, sheltered anchorages, and the right time to move makes an enormous difference to your itinerary. The Ionian chain — Corfu, Lefkada, Ithaca, Kefalonia, Zakynthos — has softer winds (the maistros fills most afternoons) and emerald waters that justify every sailing magazine cliché ever written.

The best sailing season runs late April through October. May, June, and September are ideal: warm water, reliable winds, fewer crowds, and lower marina prices. July and August bring the meltemi at full force and packed anchorages — conditions that reward experience and punish preparation shortcuts. A good skipper will time your passages, know which anchorages to book ahead, and have contingency plans for when the meltemi decides to overstay its welcome.