Stark and windswept Pantelleria may be the chicest island getaway in all of Europe. All over this 86-sq.-km (33-sq.-mile) island, striking black rock sets off the green vegetation and glorious blue of the Mediterranean. Pantelleria is an exotic place caught between two continents and two cultures, and behind a down-and-out port town lies a countryside with some of the most exclusive accommodations in the world. Although ciaos are exchanged on the street (and it's mostly Italians who vacation here), Pantelleria's whole look and feel are a world away from the entrenched civilization of mainland Italy or even Sicily, from which it is removed by 110km (68 miles) of open sea. Architecturally and gastronomically, Pantelleria has more in common with North Africa, just 70km (43 miles) to the east.
Pantelleria's rich ancient history includes the usual suspects of Mediterranean squatters -- Phoenician settlers named it Cossyra and were later subjugated by Rome, then Byzantium, and then Arabs, who called the island Bent El Rion ("daughter of the winds"), from which "Pantelleria" derived. The Arabs were here from 700 to 1123, and they left a significant legacy on the island, first and foremost in the dammusi (a form of stone house that exists nowhere else in the world) that riddle the island. Nearly all of these ancient structures have been converted into vacation rentals or miniresorts, and staying in one is integral to the Pantelleria experience.
These days, the most well-known squatters on Pantelleria are the glitterati of European fashion and media. An elite set of designers, actors, photographers, and editors come here to escape the flash and chaos of their real worlds. Giorgio Armani was the first Big Name to buy property here, and he stills summers in an elaborate compound of dammusi called Casa Armani, and he still goes for aperitivo at Bar Aurora in working class Pantelleria town. But don't come to Pantelleria expecting any overt glamour or you'll be sorely disappointed: Pantelleria is the anti-Sardinia, Capri, and Panarea in its lack of nightlife, glitzy boutiques, and showy scene. You will meet real locals here, and they are friendly and warm. But they aren't walking around in Tod's resort wear and chic linen caftans. The real Pantelleria is endearingly indifferent to what an exclusive place it has become.
Before you go booking the next flight to this still-insider place, some disclosure is in order on the physical nature of Pantelleria: It isn't for everyone. The summer sun is unequivocally oppressive, and even on otherwise mild spring and fall days, the scirocco wind, carrying dust from the Sahara, can send you running for cover. Near constant wind keeps the skies clear, so clouds are unheard of, but then so are sandy beaches on this lavic outcrop -- a key detail to keep in mind when thinking about what your days will look like here. Pantelleria's lava shores are inhospitable for the normal "island" pursuits of baking in the sun, and even going for a swim is a bit of a process here, almost always involving a drive along a steep and winding road, then a 10-minute scamper down a bumpy trail to water's edge, then donning aqua socks to protect your feet from the jagged bottom once you actually wade in. The antagonism of nature on Pantelleria, more than its remoteness, has kept mass tourism at bay.
However, the rewards for your suffering of heat, wind, rough rocks, and carsickness are indelible experiences. The sea off Pantelleria is uncontaminated in extremis: Near the shore, the water seems like a liquid form of internally flawless emerald, while a bit farther out, the color changes to deep cobalt, as the sea bottom drops off sharply. Stunning nature, from the elephant's trunk rock formation called Arco dell'Elefante to the warm sulfuric lake of the Specchio di Venere, makes a lasting impression. And the sense of isolation is profound. Pantelleria is about as close as you can get to the end of the Earth while still being technically in Europe.