If you like having your cultural compass skewed, you'll love Pantelleria. The map says Italy, but everything about the island spells North Africa. Villages have names like Bukkuram, Bugeber, and Gadir. Dwarfed by palm trees and built of rough volcanic stone, clusters of one-story cubic dwellings with humped roofs erupt from the prickly black-brown landscape like oases. The port's architecturally challenged concrete apartment blocks and souk-like alleyways lend it the louche, scrappy allure of Tangier. The heat is the heat of the desert, with sun so strong that only crazies leave the cool of a shop awning to cross the street without first picking out a patch of shade on the other side. Citrus trees are grown in circular, high-walled giardini arabi that protect them from the wind. Locals count the days until restaurants serve the weekly special—fish couscous.
I first visited Pantelleria, which is marooned in the strait between Sicily and Tunisia and has a mere 32-mile perimeter, in 1984, when I went to do a story on the house of its most famous (part-time) resident, Giorgio Armani. This may sound ungrateful, but I have been angry with Mr. Armani ever since. He insisted I stay at his compound, causing me to only half-discover the island. Now, I know that a lot of people would sell their mother to be spoiled the way one of the world's richest fashion designers spoils houseguests such as Jodie Foster, but you cannot drape yourself on a chaise longue all day while a housekeeper irons your pool towels and expect to get the feel of a place. Also, I didn't have a car. I was a prisoner, Mr. Armani my warden.
Eighteen years is a long time to nurse a hunger. I don't recommend it. Having had a small bite of Pantelleria, I was primed to return for the banquet version. Unlike in the mid eighties, however, when even the most well-traveled people I knew looked politely dazed when I mentioned the island, on my second trip I would have to share it. For in the interval Pantelleria had acquired buzz. Sting had been and loved it. A little lady called Madonna dropped in with her family—and her yogi—for a summer holiday. Gérard Depardieu and fashion photographer Fabrizio Ferri bought property. Wolfgang Puck was filmed at the caper cooperative for a segment on the Food Network. Manhattan grocer Eli Zabar, who owns a house near mine in Provence and has his own plane, taunted me by saying he flies to Pantelleria from Avignon—for lunch. And I'd learned from Florentine beauty Sciascia Gambaccini, a fashion editor at Jane and Glamour magazines who has the most sensational house on Pantelleria, that the island finally has a couple of hotels a person would actually want to stay in.
One thing that hasn't changed is how difficult it can be to get there. A seven-hour overnight ferry from Sicily would have been below my comfort level, so I elected to fly from Palermo. But just as Gambaccini had predicted, the local carrier didn't just cancel my flight—it erased the route altogether. Stranded and gently fuming, I took a train across the island to Trapani. Rage gave way to exhilaration as beautifully framed pictures of the cerulean coast, craggy backcountry, and Sicily's famed elevated highway system clicked by like a slide show. In Trapani the only thing that stood between me and Pantelleria was a puddle-jumper. Touching down on a grilling afternoon in June with a friend whom I had been promising (and promising and promising) to bring to the island, I felt as if I'd earned a reception committee.
Since my goal this time was to experience Pantelleria the way islanders themselves do, I rented the local car of choice, a standard-issue seafoam-green Fiat Panda in the comical shape of a shoebox. Cushiness is not one of the vehicle's virtues, but the Panda was good at navigating the island's chilling switchbacks and the sheer, stony path leading to the dammuso (as traditional Pantescan houses are known) that we'd rented. Because it is the property of the same grand family that owns the Regaleali vineyards in Sicily, where I have visited them, it never occurred to me that the house wouldn't be perfect.
The views were. The cane-shaded terrace overlooked the coast, where centuries ago streams of lava formed black fingers pointing into the sea. Inside, however, we found thin beds (insanely arranged so they faced away from the water—we instantly swung them around), a shower that flooded the bathroom, and a woefully underequipped kitchen. But then, what else is new?Does anyone ever totally fall in love with his vacation rental?Although there are spectacular houses to let on Pantelleria, such as Gambaccini's, ours was like every villa I've ever had (and paid lots more money for) in the Aegean. And sucking it up wasn't all that painful, knowing that later in the week we'd be test-driving the most luxurious hotel on the island.
While every Pantescan has his own ideas about how first-timers should get to know the island ("climb the Montagna Grande," "have a bag of fig-filled mustazzoli cookies"), a drive on the ring road is a good, sweeping introduction. Circling Pantelleria at a relaxed pace took two hours and made me completely sick. You could roll the credits of a film about the early days of our planet over a shot taken on the steep southeast coast, but for sufferers of vertigo, I don't suggest lingering. From a gentler perch above casa Armani, known to any traveler worth the Hello! magazine in his beach bag, we spied the mature palms, reportedly stripped from a boulevard in Palermo, that are an endless source of island gossip and envy. (These days the designer is locked in a palm-tree war with Ferri: if one buys 200, the other buys 400.)
A couple of miles along, past terraced fields where hunched, motionless figures picked capers one by one, we cooled off with a half-crate of white peaches purchased on the side of the road from the back of a three-wheeled truck. If we had wanted a just-caught 50-pound swordfish, we could have had that, too. Arco dell'Elefante is a natural rock formation that looks like an elephant taking a big swig of the Mediterranean; enacting a Pantescan rite of passage, we went for a magical swim under its arcing trunk. And at the Lake of Venus's Mirror we dutifully stopped to remember Madonna, who—barefoot, pregnant, and caked in therapeutic mud—was viciously nailed by the paparazzi there three years ago.
The island has barely a stoplight, as we discovered, and no FedEx trucks hogging its wild fennel-fringed lanes. Despite celebs on heavy MTV rotation, Pantelleria has maintained the elemental aura of a last frontier, of an antique civilization shaped by the Phoenicians, Egyptians, Greeks, Romans, Normans, Genovese, Spanish, and Bourbons. Of the island's many occupiers, none left a more lasting trace than the Arabs, who launched their conquest in the eighth century, planted the first grapevines and olive trees, and stayed on for 200 years to tend them.
Continuing an ancient tradition of insularism, Pantelleria cultivates tentative relations with the outside world. Places offering Internet connections come and go, but mostly they go. In a café one afternoon we were entertained by a booker from a Milan modeling agency in bug shades who staged a public meltdown over not being able to pick up her e-mail. Two gas stations service the entire island, and many shops and restaurants don't take credit cards. At U Trattu—a populist trattoria with its own boccie court, the best mulberry cremolata, and waiters as round as Botero sculptures—we found that knowing Italian is sometimes not enough: locals speak a dialect that defeats even mainland Italians. A woman I became friendly with told me to write to her care of the garage where she gets her car fixed in the port town of Pantelleria, because she was more sure of receiving her mail there than at her rural dammuso.
With the countryside so easy to love, we never expected Pantelleria town to put up such a fight. Our first sortie was daunting, with each of us doing his best to pretend that he loved what he was seeing. As we approached the center, bombed-out bits of beachfront gave way to abandoned lots vibrating with gorgeous weeds. Stray dogs roamed the quays before a brooding Norman fort, one of the few buildings left standing after the Allies bombarded the town in World War II. Grocery shops were poky, dimly lit, and so overstocked that we had to turn sideways to get past the towers of bottled water. The terraces of the cafés seemedÉwellÉkind of tacky. We had chosen the verity of Pantelleria over the spit and polish of a place like Capri, deriding the latter as Italy Lite. But suddenly Capri was looking pretty good.
WHERE TO STAY
Monastero Dammusi from $2,850 per week. Contrada Kassà, Scauri Alta; 39-02/581-861; www.monasteropantelleria.com
Santa Teresa Doubles from $130. Contrada Monastero Alto, Scauri Siculo; 39-0923/916-389; www.santateresa.it
Buckland & Abeti This company rents the best, most stylish dammusi on the island. Sciascia Gambaccini's spectacular compound, for example, sleeps up to 12 people in four guesthouses. Houses from $1,535 per week; 39-055/284-828
WHERE TO EAT
U Trattu Dinner for two $40. 2 Via Gabriele, Rekhale; 39-0923/918-356
La Risacca Dinner for two $55. 65 Via Milano, Pantelleria Town; 39-0923/912-975
La Nicchia Dinner for two $75. Contrada Scauri Basso, Scauri; 39-0923/916-342
La Conchiglia Lunch for two $60. Contrada da Khamma Conitro; 39-0923/915-333
La Vela Lunch for two $55. Scauri Scalo, Scauri; 39-0923/916-566
Ristorante Castiglione Franco Dinner for two $45. 24 Via Napoli, Pantelleria Town; 39-0923/911-448
La Pergola The first choice of locals for swordfish involtini and spaghetti with sea urchin. Dinner for two $55. Contrada Suvaki; 39-0923/918-420
CAFÉS, BARS, AND BAKERIES
Il Goloso 39 Via Borgo Italia, Pantelleria Town
Caffè Aurora 36 Via Borgo Italia, Pantelleria Town
El Tikirriki 2-3 Via Borgo Italia, Pantelleria Town
Panificio Carmelo Giuffrida Excellent pizza. 21 Via Borgo Italia, Pantelleria Town
Da Giovanni The island's best pastries. Piazza Cavour, Pantelleria Town
SHOPS
Cooperativa Agricola Produttori Capperi The source for Pantelleria's famed capers. 11 Via del Cappero, Scauri Basso; 39-0923/916-079
Lillo Antonioni A producer of passito, the Pantescan sweet wine. Contrada Bugeber, Bugeber; 39-0923/914-025
Enopolio di Pantelleria The place to stock up on all types of local wine. Via Balate, Contrada da Arenella; 39-0923/912-556
La Nicchia Pantescan olive oil and oregano, transportable sauces, preserved eggplant and zucchini, marmalades, jellies, and more from the people behind the restaurant. 24 Via Messina, Pantelleria Town; 39-0923/912-968