233km (126 nautical miles) SE of Piraeus
This is one of the most spectacular islands in the world. Many Greeks joke, somewhat begrudgingly, that there are foreigners who know where Santorini is -- but are confused about where Greece is! Especially if you arrive by sea, you won't confuse Santorini with any of the other Cyclades. What will confuse you is that the island is also known as Thira. While large ships to Santorini (pop. 7,000) dock at the port of Athinios, many small ships arrive in Skala, a spectacular harbor that's part of the enormous caldera (crater) formed when a volcano blew out the island's center sometime between 1600 and 1500 B.C. To this day, some scholars speculate that this destruction gave birth to the myth of the lost continent of Atlantis.
The real wonder is that Santorini exceeds all glossy picture-postcard expectations. Like an enormous crescent moon, Santorini encloses the pure blue waters of its caldera, the core of an ancient volcano. Its two principal towns, Fira and Oia (also transliterated as Ia), perch at the summit of the caldera; as you approach by ship, bending back as far as possible to look as far up the cliffs as possible, whitewashed houses look like a dusting of new snow on the mountaintop. Up close, you'll find that both towns' main streets have more shops (lots of jewelery shops), restaurants, and discos than private homes. If you come here off season -- say in early May -- you'll still find Fira's streets, shops and restaurants crowded. In August, you'll experience gridlock.
Akrotiri is Santorini's principal archaeological wonder: a town destroyed by the volcano eruption here, but miraculously preserved under layers of lava. As soon as you reach Santorini, check to see if Akrotiri is open; the site's protective roof collapsed in 2005 and the site has been totally, or partially, closed since then. If Akrotiri is closed, don't despair: If it weren't that Akrotiri steals its thunder, the site of Ancient Thira would be the island's must-see destination. Spectacularly situated atop a high promontory, overlooking a black lava beach, the remains of this Greek, Roman, and Byzantine city sprawl over acres of rugged terrain. Ancient Thira is reached after a vertiginous hike or drive up (and up) to the acropolis itself.
Arid Santorini isn't known for the profusion of its agricultural products, but the rocky island soil has long produced a plentiful grape harvest, and the local wines are among the finest in Greece. Be sure to visit one of the island wineries for a tasting. And keep an eye out for the tasty, tiny unique Santorini tomatoes and white eggplants -- and the unusually large and zesty capers. Most importantly, allow yourself time to see at least one sunset over the caldera; the best views are from the ramparts of the kastro and from the footpath between Fira and Oia.
The best advice we can offer is to avoid visiting during the months of July and August. Santorini experiences an even greater transformation during the peak season than other Cycladic isles. With visitors far in excess of the island's capacity, trash collects in the squares, and crowds make strolling the streets of Fira and Oia next to impossible. Tip: Some accommodations rates can be marked down by as much as 50% if you come off season. Virtually all accommodations are marked up by at least as much for desperate arrivals without reservations in July and August.