Destination: Taormina, Sicily

Your Chic Travel Guides: Luna Scamuzzi and Paolo Mandelli, the husband and wife founders of Lucifer Vir Honestusfine jewelry in Milan.

Stay

Long before Ian Schrager, there was the Prince of Cerami who converted a 15th-century monastery into the San Domenico Palace Hotel in the second half of the 1800’s to accommodate an earlier version of jet setters on the Grand Tour. With its long-range views of Mount Etna and the sun-dappled sea, coupled with romantic cloisters and lush, scented gardens, the hilltop property continues to enchant guests to this day.

After settling into a bayside suite, which will explain why so many famous creative types have stayed, stroll through the private grounds and relax poolside or at a nearby pebbled beach easily accessed on a complimentary hotel shuttle.

Book a table at Principe Cerami, the two Michelin-starred restaurant helmed by chef Massimo Mantarro. His menu blends the island’s classic ingredients such as sea urchin, ricotta and eggplant with haute cuisine preparation and presentation down to dessert’s glorified interpretation of cassatina. End the evening with drinks at the Cloister Lounge, an al fresco bar that oozes Old World glamour.

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See

Besides the Ionian Sea, travelers come to Taormino for the homemade pastries and immense Teatro Greco, certainly the town’s most well-known attraction since the time of its construction approximately 2,000 years ago. Unlike many ancient sites, the Greco-Roman amphitheatre is stilled used for a range of performances and events like film festivals. Listening to a world-class orchestra or opera against the backdrop of Mount Etna is a sublime must.

Eat

Italian for the black cap, La Capinera is chef Pietro D’Agostino’s Michelin-starred, Slow Food-propelled pride and joy. From its seaside perch to traditional, fresh fare, the restaurant specializes in authentic Italian repasts. A sea bass ragout and baby cuttlefish come in primi piatti of black tagliolini or spaghetti, respectively. If it’s listed, Mandelli also suggests the carbonara di mare. Follow with Mediterranean seafood soup or snapper filet to save room for cannoli with blood orange sorbet.

For incredible sunset views, often accompanied by deejay sets, head to Hotel Imperiale’s rooftop restaurant OpsoN. The chef, who hails from a top Milanese kitchen, knows his way around breadcrumbs and squash blossoms.

More Tips: Leave the diet at the door at Pizzeria Vecchia on a hidden alley. It’s also worth the drive to the Medieval town of Randazzo for San Giorgio e il Drago, whose impeccable wine list matches its charming cellar location.

Pottery & Pastry

One glimpse of Corso Umberto, the main shopping drag, and it’s obvious that ceramics are the key to Taormino’s heritage. From the sea of options, a good place to start is Saro Russotti. Sicilian wines seem to be all over American menus these days, so check out the real deal at La Cantina del Sole wine shop owned by Giuseppe D’Angelo. You can’t go wrong with sweets on an island that’s the birthplace of the cannoli. Though every pastry shop in Taormina is excellent according to our guides, some popular picks are Etna, Chemi and Minotaura. One bite, and you’ll extend your trip.

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