5 Best Sights in The Cyclades, Greece

Founded in 1870, the Koutsoyannopoulos Winery offers a tour of its old facility, now a multiroom museum that is picturesque, authentic, and mostly underground. Tools, techniques, and the original business office are from a world long gone—but the wines, as the ensuing tasting proves, are contemporary and refined. The Wine Spectator rated their Assyrtiko among the world's top 100 whites. To add your own kudos, note that this admired winery is open year-round.

A Dorian city—with 9th-century BC tombs, an engraved phallus, Hellenistic houses, and traces of Byzantine fortifications and churches—floats more than 2,100 feet above the island. At the Sanctuary of Apollo, graffiti dating to the 8th century BC records the names of some of the boys who danced naked at the god's festival (Satie's famed musical compositions, Gymnopédies, reimagine these). To get here, hike up from Perissa or Kamari or take a taxi up Mesa Vouno. On the summit are the scattered ruins, excavated by a German archaeology school around the turn of the 20th century; there's a fine view.

Santorini's most popular beach, one of several excellent stretches of sand on the southern end of the island, manages to maintain its beauty despite an onslaught of sunseekers. The black sands are backed by dramatic cliffs, including the one topped by Ancient Thira. A steep path from one end of the beach leads up to the ruins, past a refreshing and very welcome natural spring, but most beachgoers don't venture beyond their umbrella-shaded loungers or the long line of beach bars and tavernas. Amenities: food and drink; showers; toilets; water sports. Best for: snorkeling; swimming; walking.