Drop anchor off Ano Syros, the medieval hilltop settlement that crowns the island's northern peak above Ermoupoli — one of the most visually striking backdrops you'll find in the Cyclades. The whitewashed Catholic quarter, Venetian-era architecture, and winding alleys spilling down the hillside give this spot a distinctly different character from typical Cycladic anchorages. It's worth rowing ashore to explore the labyrinthine streets and the 13th-century Cathedral of San Giorgio at the summit.

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