144km (78 nautical miles) SE of Piraeus
Siros is very different from the other Cycladic islands. The capital, Ermoupolis, is not a cute Cycladic sugar-cube miniature town, nor a ramshackle port town, but the administrative capital of the Cyclades, with a large shipyard. If you live anywhere in the Cyclades and need a building permit, or a license, or a lawyer, you'll end up making at least one trip here. Consequently, Ermoupolis has a year-round businesslike bustle totally unlike any other town in the Cyclades.
Ermoupolis has been the most important town in the Cyclades almost since it was founded in the 1820s by a flood of refugees from Asia Minor and the eastern Aegean islands. The settlers named the town after Hermes, the god of merchants. The name seems to have been an excellent choice: Soon, this was the busiest port in Greece -- far busier than Piraeus -- and a center of shipbuilding. You'll see several still-functioning shipyards and dry docks along the harbor. Just inland are neighborhoods with handsome neoclassical mansions built by shipping magnates. When you walk into Plateia Miaoulis, the main square in town, you may find it hard to believe you're still in the Cyclades: The square is lined with truly grandiose public buildings, including a town hall that could hold its own beside any government building in Athens. Just off the Plateia is the Apollon Theater, a miniature of Milan's La Scala Opera House, with a summer music festival. Climb uphill from the Plateia Miaoulis and you'll find yourself in the oldest part of town, Ano Syros, which happens to be a little sugar-cube Cycladic neighborhood, albeit one with both a Capuchin and a Jesuit monastery. Although Ermoupolis saw a considerable period of decline in the 20th century, recent restoration efforts have brought back much of the city's glory; the entire town is now a UNESCO World Heritage Site.
I have to confess that Siros is one island where the capital town's pleasures are so considerable that I don't mind neglecting the island itself. That said, the north end of Siros is a starkly beautiful region of widely dispersed farms, multilayered terraced fields, and village-to-village donkey paths and footpaths. Some of the island's best beaches are here, many accessible only on foot or by boat. The south is gentler, with a number of villages with the 19th-century country villas of the wealthy shipping magnates who had both a town house and a summer retreat; the villages of Manna, Ano Manna, and Dellagrazia have especially impressive villas. Throughout the island, the San Mihali and kopanisti cheeses are made, and delicious thyme honey is produced.
The best months to visit Siros are May, June, and September; the worst month is August. That's when vacationing Greek families -- many bringing with them at least two cars -- pour into their villas here, with the overflow taking up virtually every hotel room on the island. If you want to tour the island, having a car is the best way to get around, although bus service to the more settled, southern part of the island is good.