And then there’s the romantic and oft-repeated story about German painter Otto Geleng, who visited in 1863 and created a sweeping panorama of Taormina featuring the sea, olive tree-dotted slopes and the Greek Theatre, with Mount Etna looming in the distance. When he showed his work to his colleagues in Paris, they believed he’d simply imagined the views that he’d depicted. He urged them to visit, even betting them that if the reality of Taormina differed at all from his work, he’d pay for their travel expenses. History records he won the bet.

Shoppers browse kitschy souvenir stores squeezed beside luxury boutiques from the likes of Fendi, Dior and Patek Philippe. Here the must-have emblem is the testa di Moro, a pair of heads symbolic of Sicily that appear on magnets, ceramic knick knacks and a hundred other decorative tchotchkes. They tell yet another bloody, salacious story that contrasts with the breezy, Mediterranean surroundings: a local girl falls in love with an Arab prince and, when she finds out he plans to abandon her to return to his wife and family across the sea, kills him in a fit of rage and turns his head into a vase.

Teenagers spill out of a score of gelato stalls licking cones, becoming unwitting witnesses to a wedding as guests crowd the entrance of the 17th century Church of Saint Catherine of Alexandria. Passing by again later that afternoon, another couple poses in the same spot for engagement photos.

But there’s more to the town than entertainment trivia and historical architecture. As you might expect from an Italian destination, there are plenty of local delicacies to devour. Family-owned Pietradolce winery produces tipples whose terroir includes the lava flows of Mount Etna, no less. (The volcano erupted as recently as May 14 – Geleng himself would have wanted that selfie!) Take an ape calessino – think an Italian tuk-tuk, inspired by old fruit delivery carts – up the hill to Castelmola village and you can sample the area’s first almond wine, created at Antico Caffè San Giorgio. Diners lap up granita at cosy alfresco tables in front of the colourfully painted Bam Bar, while at seaside Mazzarò – recommended by Dolce himself in an interview with Condé Nast Traveler – beachgoers bite into fist-sized servings of arancini.

The well-to-do of yesteryear clearly made sure to stop off at Taormina during their Grand Tour for a reason. Although you won’t necessarily end up the protagonist of a romantic thriller during your stay, you’ll nevertheless find yourself seduced – and possibly inspired.

What to Pack

Carpazi shirt (US$1,160) by The Row at Net-a-Porter.

Midi skirt (US$1,110) by Dolce & Gabbana at Mytheresa.

Aquazzura Tequila sandals (US$925).

Buccellati Rombi earrings (US$21,700).