7 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 bewildering maze of twisting cobblestone streets, arched porticoes, and towering doorways, the Old Town plunges you alternatively into cool darkness and then suddenly into pockets of dazzling sunshine. The Old Town is divided into the lower section, Bourgos, where the Greeks lived during Venetian times, and the upper part, called Kastro (castle), still inhabited by the Venetian Catholic nobility.

The Tinians built the splended Church of the Annunciate Virgin on this site in 1823 to commemorate finding a buried icon of the Annunciation in the foundations of an old Byzantine church that once stood here. Imposing and beautiful, framed in gleaming yellow and white, it stands atop the town's main hill ("hora"), which is linked to the harbor via Megalochari, a steeply inclined avenue lined with votive shops. Half Venetian, half Cypriot in style, the facade (illuminated at night) has a distinctive two-story arcade and bookend staircases. Lined with the most costly stones from Tinos, Paros, and Delos, the church's marble courtyards (note the green-veined Tinian stone) are paved with pebble mosaics and surrounded by offices, chapels, a health station, and seven museums. Inside the upper three-aisle church dozens of beeswax candles and precious tin- and silver-work votives—don't miss the golden orange tree near the door donated by a blind man who was granted sight—dazzle the eye. You must often wait in line to see the little icon, encrusted with jewels, which is said to have curative powers. To beseech the icon's aid, a sick person sends a young female relative or a mother brings her sick infant. As the pilgrim descends from the boat, she falls to her knees, with traffic indifferently whizzing about her, and crawls painfully up the faded red padded lane on the main street—1 km (½ mile)—to the church. In the church's courtyards, she and her family camp for several days, praying to the magical icon for a cure, which sometimes comes. This procedure is very similar to the ancient one observed in Tinos's temple of Poseidon. The lower church, called the Evresis, celebrates the finding of the icon; in one room a baptismal font is filled with silver and gold votives. The chapel to the left commemorates the torpedoing by the Italians, on Dormition Day, 1940, of the Greek ship Helle; in the early stages of the war, the roused Greeks amazingly overpowered the Italians.

Monastery buffs should head to Ano Mera, a village in the central part of the island, where the Monastery of the Panayia Tourliani, founded in 1580 and dedicated to the protectress of Mykonos, stands in the central square. Its massive baroque iconostasis (altar screen), made in 1775 by Florentine artists, has small icons carefully placed amid the wooden structure's painted green, red, and gold-leaf flowers. At the top are carved figures of the apostles and large icons depicting New Testament scenes. The hanging incense holders with silver molded dragons holding red eggs in their mouths show an Eastern influence. In the hall of the monastery, an interesting museum displays embroideries, liturgical vestments, and wood carvings. A good taverna is across the street. The monastery's big festival—hundreds attend—is on August 15.

In an old neoclassical mansion, once destroyed in the big earthquake, the museum has an enticing collection. Pieces include ships' figureheads, seamen's chests, maritime equipment, and models which reveal the extensive nautical history of the island, Santorini's main trade until tourism took over.

To peer into a live, sometimes smoldering volcano, join one of the popular excursions to Nea Kameni, the larger of the two Burnt Isles. After disembarking, you hike 430 feet to the top and walk around the edge of the crater, wondering if the volcano is ready for its fifth eruption during the last 100 years—after all, the last was in 1956. Some tours continue on to the island of Therassia, where there is a village. Many operators on the island offer volcano tours.

A backdrop of red-and-black volcanic cliffs adds no small amount of drama to this strand of multicolored pebbles and red-hued sand, and the timelessness of the place is enhanced by the presence of nearby ancient Akrotiri. Crowds sometimes pile in during July and August, and a few too many loungers and umbrellas detract from the stunning scenery, but for the most part this is one of the quieter beaches on the south side of the island. There's a rough path from the parking area to the beach. The beach has been known to close due to rocks falling, and entering would be at your own risk. Amenities: food and drink; parking (about €2, not always imposed). Best for: snorkeling; swimming.