17 Best Sights in Santorini (Thira), The Cyclades

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.

The closest sand beach to Ia is handy when you don't feel like making the trip to more famous beaches on the south end of the island. It's not that there's anything second-rate about this beautiful spot: the cliff-backed strip of sand is rarely crowded; the sea floor is sandy, too, providing nice wading for kids and a pleasant experience when splashing around in the surf; and the cliffs provide welcome shade. A downside is the summertime meltemi winds, which churn up the surf and sand. Islanders used to grow fruits and vegetables down here, and the name comes from the Turkish word for garden, baxes. Amenities: food and drink; parking (free). Best for: surfing (at times); swimming.

The first of the island's wineries to open to the public puts on a big show, with a bright, view-filled tasting room surrounded by vineyards. A distinctly Santorini experience is a taste of Kallisti, a version of the Assyrtiko variety, and the exceptional Estate Argyros Vinsanto, an international award winner.

Growing the best Greek grapes has everything to do with the land, and the oenologists at Domaine Sigalas, on the ancient plain of Ia, are happy to share their knowledge of the unique Santorini soil and over three millennia of winemaking on the island. A respected name in Greek wines, the family-run winery has opened up its lush inland vineyard at Baxes for tastings and food pairing sessions. Groups are kept small and are priced from €50 per person.

One of the oldest vineyards, this winery has been exporting its distinguished produce since the days when mules carted wine-filled goatskins to the port in Fira. Tastings in the atmospheric old storage and pressing rooms include Voudomato, a native dry rosé, and Nykteri, a sophisticated white from the island's indigenous Assyrtiko grapes—the name means "working the night away," because the grapes have traditionally been harvested at night to avoid damage from the heat.

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.

Standing on the highest point on Santorini, which rises to 1,856 feet at the summit, Santorini's largest monastery offers a cinematic vista: from here you can see the surrounding islands and, on a clear day, the mountains of Crete, more than 100 km (62 miles) away. You may also be able to spot ancient Thira on the peak below Profitis Ilias. Unfortunately, radio towers and a NATO radar installation provide an ugly backdrop for the monastery's wonderful bell tower.

Founded in 1711 by two monks from Pyrgos, Profitis Ilias is cherished by islanders because here, in a secret school, the Greek language and culture were taught during the dark centuries of the Turkish occupation. A museum in the monastery contains a model of the secret school in a monk's cell, another model of a traditional carpentry and blacksmith shop, and a display of ecclesiastical items.

This is the treasure house that displays frescoes and other artifacts from the famed excavations at Akrotiri. Many of the finds have been sent off to the Archaeological Museum in Athens, but the most charming fresco remains here: a colorful depiction of women in dresses, gathering saffron from the stamens of crocuses. Also in this small collection are fresco fragments with the famous painted swallows (the island's favorite design motif) that still flock to Santorini to roost on the cliffs. The fossilized olive leaves from 60,000 BC prove the olive to be indigenous.

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.

The modern Greek Orthodox cathedral is a major landmark. It's worth a look inside for a view of the frescoes by local artist Christoforos Asimis. You'll quickly note how the local priests, with somber faces, long beards, and black robes, look strangely out of place in summertime, tourist-jammed Fira.

Upper Fira's exhibition hall, named for the famous ship owner, hosts many international conferences as well as concerts. Visitors can admire acclaimed seasonal exhibitions that reflect the culture and nature of the island through painting and sculpture.

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.