The Cyclades are the Greece of the imagination — white villages on brown rock, square-rigged chapels, bays with water like glass in the morning and a milk-white sea by four. The engine of both beauty and trouble is the meltemi: a dry north-easterly that blows hardest from late June through August, typically building through the morning, peaking in the afternoon at forces five to seven in its determined moods, and easing at dusk. A week here planned without the meltemi is a week spent motor-sailing into it. A week planned with it starts north and works south, keeps the long legs for the morning, and treats the afternoon as what it is — siesta, swimming and a taverna table with a view of other people's spray.
This is a routing guide built on standard meteorological characterisation of the area and published pilot information; the forecast on the day always outranks the plan.
The strategic idea: north first, south later
Base out of Lavrion or Athens and clear north to Kea or Andros territory early in the week while the schedule is flexible, then let the week run downwind through the middle islands — Paros, Naxos or Mykonos according to taste — and finish in the southern group, where the escape back to base is a shorter close reach if a blow settles in. The reverse order, the one brochure itineraries quietly assume, puts the return leg to weather exactly when the week is tired and the forecast is deciding things.
The daily rhythm
Under way by eight or nine, anchored or berthed by one, and nothing that matters scheduled for the afternoon except lunch. The meltemi's schedule is the week's schedule: the bays on the islands' southern and western lee shores carry the flat water, and the ferry harbours — Paroikia, Naxos town, Mykonos' new port — are the reliable all-weather night stops when the forecast has teeth. In the strong-mood weeks, the professional answer is to stay two nights somewhere lovely rather than prove a point; the islands are close enough that a lost day costs one bay, not the trip.
Which islands buy what
Kea opens the arc quietly. Mykonos is the nightlife tax with the worst shelter-per-glamour ratio in the group — take it on a calm forecast or from the north at dawn. Paros and Naxos are the working heart: big bays, real towns, tavernas, and enough lee options for most wind directions. The small islands — Iraklia, Schinoussa, Koufonisia — are the meltemi-week prizes, reached on the moderate days and worth the forecasting patience. Milos, far south-west, is the flex: a genuine destination with a huge bay, best taken as the week's finale when the wind allows and dropped without grief when it doesn't.
Who should skip the Cyclades in high summer
Guests who need firm daily itineraries, marina comfort every night, or their sailing smooth: this is a sea state that respects planning and punishes schedules, and July's meltemi weeks are no place to discover that. The same waters in June or late September — or the Saronic and Argolic next door — deliver the Greece with half the wind lottery. For crews who enjoy the game, there is no better board in the Aegean.