The villages of Santorini are remarkably varied. Considering that this is an island of barely 28 square miles, with a population of about 15,500 people crammed close together in about a dozen places, the different character of each settlement is fascinating. The distinctions among the towns are also worth knowing before you go because it can make a big difference in the kind of vacation you have once you get there.
By the way, there are no actual towns on Santorini. The whole island (and the nearby island of Thirassia that faces it across the caldera) is part of one municipality, Thira (also the official Greek name of the island and the posted destination of ferries and flights from within Greece). Nevertheless, for visitors, it's useful to understand how these settlements differ.
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The colorful village of Oia (pronounced EE-ya) is perched on the cliffs of Santorini's volcanic caldera, on the northern tip of the island. The village is a listed historic monument, and its residential alleys and lanes were the first in Greece to be listed as an archaeological historic monument by the Hellenic Tourism Association.
The town developed as a mostly seafaring community with troglodyte dwellings below the main street (pedestrianized Nomikos Street) carved into the face of the caldera housing sailors and crew. The more substantial, bourgeois houses above are known as captains' houses and were built for shipowners and officers. Being high up, they had a good view of their vessels passing from the port to the other islands in the Cycladic chain and northward to mainland Greece and the rest of Europe. After the departure of the Ottomans in 1850, Santorini supported more than 150 vessels that carried the island's wine across the Aegean and the Mediterranean.... Ironically these days, it's the most prestigious and luxurious five star hotels that crawl over the face of the caldera.
Things to Do: Oia today is famous for sunset viewing from the ruins of Oia's Byzantine castle, probably the most famous spot on Santorini. That's because there is an unobstructed view westward, making it the perfect spot to watch the sun set into the sea. Every evening, thousands of people crowd the tight little streets and winding steps of Oia for the sunset. On the days when cruise liners dock in Santorini, the streets are as packed as Times Square on New Year's Eve. Wait until half an hour after sunset and the streets, shops, and restaurants will be much less crowded.
Very high-end shopping is Oia's other modern claim to fame. Shops offer jewelry and casual resort fashions at high prices. There are some tempting ceramics and artwork, but there are also quite a lot of overpriced souvenirs, mass produced for the tourist market.
After you've negotiated your way past all the shops, follow the main street northeastward around the tip of the town. There's a bright yellow photogenic church and beyond that are a couple of lovely Cycladic windmills. Stop for a bite at the modest looking meze cafe, Elinikon, to sample local beer and freshly made ntomatokeftides.
From Oia, there are steps (300 of them) winding down to Ammoudi Bay, a pleasant little port and beach with a taverna offering fresh seafood. Don't worry, there is also a road and taxi drivers brave enough to negotiate it, so you don't have to come back up the steps after a good night out.
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Imerovigli sits at the highest point of the caldera with the very best views of Nea Kameni, Santorini's black volcanic island in the center of the lagoon. There are those who will also tell you that the sunset views from Imerovigli are better than those of Oia.
This is a very quiet, mostly residential place with exquisite hotels hiding behind nondescript gates that give nothing away. Some of Santorini's best hotels are here in the caves below the clifftop path on the face of the caldera.
Things to Do: The town has a few mini-markets, a hairdresser, a snack bar, and a few restaurants. There is very little to do here beside luxuriate by your private hot tub or hotel pool, but the village is a short taxi or bus trip to Fira, the main village on the island. It's a three-kilometer walk downhill. If you do walk down, don't try to walk back up in the heat of the day—there is no shade at all.
If you have a head for heights, try hiking across the narrow path to Skaros. The ruins... of this medieval castle are really nothing more than a dramatic rocky headland that is something of a symbol of Santorini. Skaros castelli is probably the oldest of the castle remains on the island, and at one time, an entire village was built on its slopes. You will have to use your imagination because earthquakes and volcanic eruptions altered that landscape centuries ago. Along the way, stop to catch your breath and take in the views from the small church of Agios Ioannis Apokefalistheis.
Tips: If you walk any distance, take the clifftop path rather than the paved road. There are no sidewalks, and it can be very nerve-wracking when cars and enormous buses come barreling along the narrow road.
For dinner with good sunset views, book the Aegeon Restaurant on the clifftop path in Imerovigli. The restaurant serves reasonably priced, traditional Santorini and Greek island fare from a spacious terrace with views of the village and the volcano.
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Between Imerovigli and Fira lies the tranquil settlement of Firastephani. On the edge of this village is the Monastery of Agios Nikolaos, founded in 1651. It's not open to the public, but its blue domes make terrific souvenir photographs.
Firastephani sits atop some of the most breaktakingly steep cliffs on the caldera. There are very few dwellings and hotels set into these cliffs. Once you enter the village, there is a small, tree-shaded "balcony" on the edge of the cliffs. If you are hiking from Imerovigli to Fira, it's a good place to take a break, have a cool drink in the shade, and enjoy the views.
Things to Do: Just north of the village, visit the Underground Exhibition Tunnels of the Thera Foundation at the Petros M. Nomikos Conference Center. Art exhibitions are held in these cool, well lit tunnels. They cost just a few euros to visit, and the tunnels are a good place to take a break from the scalding sun. There's a wonderfully framed view of the red Nomikos... Conference Center building from the picture window at the end of the exhibition.
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Fira is the capital of Santorini. It's where the cruise ships come in and send their passengers up the cable car from the port to the town. It's also where you can catch a bus for 2 euros to virtually anywhere else on the island. (Be warned though, most buses aren't air conditioned, and their windows stay closed.)
Fira is the busiest town on Santorini and there is a lot to do.
Shopping: This is where islanders and working people shop for themselves, so while the town has its share of little boutiques and souvenir shops, it also has a lot of more normally priced shopping for things you might actually need—new memory cards for your camera, toiletries, and more.
Shops selling souvenirs, natural sponges, scented soaps, and handicrafts are crammed into an area of very narrow paths and lanes in the northern part of the town. It feels like a Middle Eastern bazaar.
Continue south, and the town spreads out and opens up. This is where you'll find affordable clothing, shoes, dry... cleaning shops and laundromats, photography studios, mobile phone shops, and even a mall, the Fabrica Shopping Center on Gold Street, near the Orthodox Cathedral.
Eating, Drinking, and Nightlife: Fira is packed with restaurants for every taste and budget. The main square is a kind of an open-air food court with lots of inexpensive takeaway places and cafes. There are even several Chinese buffet-type restaurants (Santorini is popular with Chinese honeymooners). Along the Caldera, the restaurants with views have the priciest menus. This part of the island is also where bars and music clubs stay open late. The Two Brothers Bar has DJs and is popular with the late night party crowd. The Tango Bar specializes in champagne and cocktails for a more sophisticated scene, but it also has DJ nights and full moon parties.
Culture: Fira has two of the island's outstanding museums. The Museum of Prehistoric Thera showcases many of the finds uncovered on Santorini's remarkable Minoan site, Akrotiri. They include painted ceramics, amphorae, colorful wall paintings, and jewelry.
In the Archaeological Museum, finds from digs on Santorini include sculpture from the Archaic to the Roman period, inscriptions from the Archaic to the Roman period, and vases and clay figurines dating from the Geometric to the Hellenistic periods. The red and white geometric patterned archaic pottery is especially interesting.