Photo: Klearchos Kapoutsis from Santorini, Greece · CC BY 2.0
Aegean Islands, Greece · Greece
A sailing week through the Cyclades strips the Aegean back to its elements: white villages stacked on volcanic cliffs, water so clear the anchor chain seems suspended in air, and islands of radically different character an easy day-sail apart. Out of Athens the classic line runs south - Kythnos's double-sided sand spit at Kolona, Milos's pirate coves at Kleftiko and the lunar white rock of Sarakiniko, Folegandros's clifftop Chora - before the finale, if weather allows: a mooring under Santorini's caldera wall as the villages along the rim light up at dusk. The Meltemi is the variable that makes or breaks the plan. From July it can blow 25-30 knots for days, funnelling between islands and closing harbours; skippered and flotilla boats plan around it, but if your own qualification or heavy-weather mileage is thin, hire a local skipper and learn from them. May-June and September bring gentler wind, warm water and empty anchorages. Expect from about £2,500 per person for a shared bareboat week including berthing, fuel and food - more with a skipper - and book Cyclades charters months ahead for high summer.
Prefilled for 1 May 2027 — the next best-season window. Search on partner sites — opens in a new tab.
Tour operators & guided experiences via Viator
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