Known for its shoreline of jagged volcanic cliffs and sea-formed lava inlets, the Italian island of Pantelleria sits southwest of Sicily and just 50 miles east of Tunisia — on a clear day, it’s possible to see across the strait to Kelibia.
First inhabited during the Bronze Age, Pantelleria’s 32 square miles were subsequently conquered by the Carthaginians, the Arabs, the Romans and Roger II, King of Sicily, with clusters of dammusi — whitewashed, dome-roofed stone dwellings dating as far back as the 10th century — surviving it all. By the early 1800s, the island had been tamed anew by caper farmers and winemakers. The past decades have brought yet another set of arrivals; as other glamorous coastal spots (Portofino, Sorrento) were besieged by cruise ships, Pantelleria (population 7,500) emerged as an understated holiday destination for in-the-know Italians — Giorgio Armani and the actress Isabella Ferrari both have houses here. Even now, its rugged beauty and rich history are the draws: After a day spent exploring hidden coves, including the sea sponge-encrusted grotto Sataria, whose turquoise waters are said to have been the love nest of Ulysses and Calypso, visitors gather at bars like Sesiventi, on the island’s western end, for aperitivi as the sun sets over Neolithic burial domes.
Last year, Giulia Pazienza Gelmetti, a former pro basketball player, opened the 20-room Sikelia, set in modern-day dammusi perched on a hill between the southwestern villages of Rekhale and Scauri. Inside, the hotel is soothing and cavelike, with concrete floors and golden light streaming in through the Moorish archways. Themà, the hotel’s restaurant, offers North African-inflected dishes such as fish couscous with cinnamon and caper leaves. sikeliapantelleria.com
A lush, 30-acre property near Rekhale with fruit-bearing trees — lemon, peach, persimmon — Tenuta Borgia consists of seven ancient dammusi (ranging from one to four bedrooms apiece) refit with chestnut doors imported from Calabria and, in the main house, jellyfish-like Venetian glass light fixtures. Fans of Luca Guadagnino’s “A Bigger Splash” (2015), will instantly recognize its homey kitchen with checkerboard backsplash and majolica-tiled pool. tenutaborgia.it
A family estate until 1996, Club Levante still feels more like a sophisticated friend’s home than a bed-and-breakfast. For one, it’s composed of six freestanding guesthouses and a main house, which offer privacy and stunning views (this is the island’s only ocean-facing hotel). In addition to breakfast, the kitchen serves a daily lunch, plus dinner five times a week. But the biggest draw might be the location, between the island’s most distinctive landmarks — the Faraglione, a stack of oceanic rock popular with divers, and the Arco dell’Elefante, another rocky outcrop, which resembles an elephant plunging its trunk into the sea. clublevante.com
Osteria il Principe e il Pirata
This family-owned restaurant in Punta Karace has a large deck whose tables, set with mix-and-match glassware, overlook the sea. Sourcing local ingredients, chef-owner Franca Raffaele prepares perfectly executed classics — spaghetti bottarga, octopus stew, seared mackerel — while her husband and sons serve. Non-fish lovers should try the zesty pesto pantesco, made with almonds. For dessert there are Pantelleria kisses — light-as-air fritters stuffed with sweet ricotta and dusted with powdered sugar. ilprincipeeilpirata.it
At La Nicchia, which opened in an updated dammuso in 1987, diners can watch the chefs toss their pizza dough — don’t miss the wood-fired buffalo mozzarella, prawn and zucchini pie. But the most coveted spots are in the herb-filled garden out back, where lantern-topped tables are positioned around a centuries-old orange tree. Friends sit there late into the night, enjoying southern Italian staples like roasted rabbit with anchovies. The restaurant is not to be confused with the nearby farm of the same name, which sells jars of capers packed in sea salt. lanicchia.it
Visitors to this sprawling 168-acre vineyard northeast of Mount Gibele, a grassy, now-dormant volcano at the island’s center, can walk along rows of tangled vines to see the ancient circular stone edifice that still collects rainwater to feed the underground cisterns. Nightly tasting sessions showcase Donnafugata’s best blends — including Ben Ryé, its award-winning passito, a sweet, after-dinner amber — which are paired with small plates, including bruschetta with ammogghio and mint-and-cheese ravioli. 011-39-0923915649
Specchio di Venere
Legend has it that Venus stopped at this aquamarine-colored crater lake to take in her reflection. Mere mortals can do the same and bathe in its sulfurous, 110-degree waters, which are thought to soothe aching muscles. For another natural spa experience, head south to Benikulà Cave — an ancient dry sauna with plumes of hot vapors escaping from a cleft in the stone.
La Collina di Loredana
Pantelleria may be far from Italy’s most famous museums, but thanks to Piedmont native Attilio Rappa, it isn’t wanting for great art. Thirty years after an idyllic honeymoon here, he and his art-loving wife, Loredana, bought some land in Cimillia, a hilly residential area on the island’s northwest coast. Before Loredena died in 2006, the family turned it into a public park filled with sculptures by the likes of Not Vital, Franz Ackermann, Katinka Bock, Paul Morrison and Susan Philipsz (a new piece is added annually). The park is unmarked, but Cimillia locals will be happy to point you in the right direction.
After being heavily bombed during World War II, Pantelleria Town, with its fluorescently lit groceries and dingy cafes, is considered a less picturesque part of the island. This boutique, which Maria Cristina Olivo opened in 2002, is a notable exception, with statement pieces from mostly Italian labels, including floral silk kimonos by Ibrigu, patterned ponchos by Ermanno Gallamini and laser-cut swimwear from Florence’s Frida Querida. 011-39-0923911861
Emporio del Gusto
This 15-year-old food shop is stocked with all the local specialties — dried and salted caper berries, bottarga di tonno, grape jelly and prickly pear honey — as well as festive ceramic tableware by the Palermo-born maker Susanna De Simone. Outside, there are a few tables with a view of the port, where travelers and locals alike gather for Pantescan wine and generous platters of antipasti. emporio-gusto.com