Understand
The Cyclades are the Greece of the travel posters: bare rocky islands adorned with brilliantly white cubistic villages soaring on hills above the wine-dark sea, and fringed with terrific beaches. Since all the world has discovered this, they tend to be very crowded with visitors, especially in high summer. But most visitors feel the islands' attractions are worth putting up with the crowds.
Kyklos is the Greek word for circle. Because the islands are set up in a circle around Delos the islands are named Cyclades. The best time to visit the Cyclades is May through June early season, accommodation is much cheaper and it's not that hot, or September through mid-October post season. In high summer July and August, though it's the most popular season, these islands for that reason get extremely crowded and hotel prices are at their highest; furthermore, the weather then can be very hot, and some islands may suffer water shortages. In the whole period mid-May through mid-October it's usually warm enough to enjoy the beaches, but in some years you risk unseasonably chilly weather at the beginning or end of this period. In October the weather changes and rain starts to fall. Ferry schedules are reduced out of season. The Cyclades are also famous for the constant wind called meltemi in July and August that mitigates the heat a bit.