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Winter is least desirable, as the weather turns cold and rainy; most hotels, rooms, and restaurants are closed, and ferry service is minimal. If you do go from November through April, book in advance and leave nothing to chance. The same advice applies to July and August peak season, when everything is open but overcrowded, except on Skyros. The meltemi, the brisk northerly summer wind of the Aegean, keeps things cooler than on the mainland even on the hottest days. Late spring and early summer are ideal, as most hotels are open, crowds have not arrived, the air is warm, and the roadsides and fields of flowers are incredible; September is also mild.
If you want to catch one of the Sporades’ famous religious and cultural festivals on your visit, keep the following dates in mind. The lively Carnival (February) traditions of Skopelos, although not as exotic as those of Skyros, parody the expulsion of the once-terrifying Barbary pirates. August 15 is the day of the Panayia (Festival of the Virgin), celebrated on Skyros at Magazia beach and on Skopelos in the main town; cultural events there continue to late August. Skiathos hosts several cultural events in summer, including a dance festival in July. Feast days? Skiathos: July 26, for St. Paraskevi; Skopelos: February 25, for St. Riginosi.