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The ancient Greek theatre in Taoromina, Sicily, was carved out of 100,000 cubic metres of limestone and boasts an impressive view.AMANDA RUGGERI

The ancient Greek theatre of Taormina, Sicily, was designed with serious drama in mind – and not just the costumed kind. Perched 250 metres above the Ionian Sea, the amphitheatre's 360-degree view encompasses the still-active Mount Etna, the sparkling Mediterranean, the medieval village of Castelmola and, of course, Taormina itself.

From here, the town's pastel palazzi and pretty cathedrals spread across the lush hillside like icing on a cassata siciliana, a traditional Sicilian cake.

It's hard to look away – or say goodbye. Which is why I've come back to the town for a second time.

I'm hardly the first to fall for Taormina. For millenniums, its strategic seaside position and lush agriculture have made it desirable – almost dangerously so. It was besieged by Arabs in the 10th century, the Normans in the 11th and the French in the 17th. In the Second World War, it was the target of devastating Allied bombings.

Today, Taormina's importance is of an altogether different kind: It's one of the best-known resort towns in Sicily.

With my penchant for off-the-beaten-path destinations, that made me initially wary. Fortunately, I first visited Taormina in April, just outside of the high season that draws thousands of tourists, many fresh from the cruise ships that anchor in the bay.

The shoulder season proved the perfect time to fall in love with the town (autumn would work just as well). I found myself mesmerized not only by monuments, but by moments. At Piazza IX Aprile, dubbed Taormina's "most elegant living room" by locals, bells clanged at the baroque church of San Giuseppe.

Couples sipped coffee at an outdoor café. A child on a bicycle squealed on a joyride toward the square's 13th-century tower. Far below, a sailboat coasted on the Mediterranean; far above, clouds clustered behind craggy mountains.

On my second visit, at the height of the August holidays, Taormina felt like a different town.

In the evenings, the main route through the pedestrian-only heart of the centro storico thrummed. Tourists poked through crowded boutiques and ceramics stores. The few times I had to get somewhere at a certain time (often a mistake in southern Italy), I had to dodge and weave through the shoulder-to-shoulder crowd.

Taormina has not always been so popular.

In the 1864 Handbook for Travellers in Sicily, two British authors wrote: "Taormina, a poor and dirty town of between 4,000 and 5,000 inhabitants, now represents the ancient grandeur of Tauromenium. Anywhere but in Sicily a spot so full of interest would be a fortunate to innkeepers; here there is not a locanda where the tourist can stay."

That soon changed. By the late 19th century, elite travellers poured into the hilltop town, fresh from the new railroad linking Taormina's big-city neighbour, Catania, with Syracuse and Messina.

Royals came to visit (England's King Edward VII, Germany's Kaiser Wilhelm II, Russia's Tsar Nicholas II). So did stars of academia and the arts (Nietszche, Wagner, Klimt, Freud). Luxurious hotels and restaurants quickly followed. The postwar boom brought a new wave of celebrities, including Truman Capote, Greta Garbo and Elizabeth Taylor.

Taormina is no longer such a stomping ground for literati (although the directors of the popular Taormina Arte festival, which hosts year-round performances in theatre, opera, ballet and music, might disagree). Nor are its visitors as well-heeled, thanks to the town's inclusion on cruise itineraries and accessibility by budget airlines.

Still, an aura of elegance remains. Maybe it's the graceful palaces that line the cobblestoned streets, or the surprising number of top-notch hotels and Michelin-starred restaurants. Taormina seems to have much more in common with Positano or Ravello, two rarefied Amalfi coast towns, than with any other place in Sicily. (Prices in Taormina have more in common with those destinations, too.)

Even so, Taormina gives visitors a real taste of Sicilian life. Literally. Cannoli are served up in bakeries as they should be, with a crisp shell that's filled with ricotta mixture only when the pastry is ordered. (Sweet-toothed visitors also should know that it is completely acceptable to kick off the day with a lemon granita spooned onto pieces of fresh brioche bread.)

At takeout spot Da Cristina, arancini are hand-rolled on the spot. As each ball of rice and ragu (or eggplant, or peas, or pistachio – my personal favourite) fries to a crisp, the wait becomes painful. But one bite makes even the longest line worthwhile.

Another draw? Taormina makes a convenient base for excursions elsewhere. Hop on the funicular, and you plunge 200 metres to the seaside in less than 10 minutes. From there, wander across the bridge to the romantic, tiny island of Isola Bella, or bask on the beaches, near-empty by October.

Or take a bus to Castelmola, the village above Taormina. Only the walls of the Norman castle that give the town its name remain. But the 12th-century Church of the Annunziata, built by the Norman king Roger I as thanks for his victory over the Saracens, still stands today. Of course, the views never fade: hills spotted with prickly pear cactus and almond trees, tumbling to the seaside.

But nothing beats the vista from Taormina's theatre. The ancients understood the power of Tauromenium's panoramas; that's why they built the theatre here, even though it meant they had to carve out – and cart away – 100,000 cubic metres of limestone to do so.

I wonder whether they had any idea how enduring their work would be. More than 2,000 years later, the image of the theatre graces postcards and archeology book covers worldwide.

And it's still causing those who see it in person to take a sharp breath at the sheer beauty of it all – no matter how many times they've seen it before.


The closest airport to Taormina is Catania-Fontanarossa Airport, 65 kilometres away. Alitalia, Delta and Air Canada all offer flights from Toronto to Catania, with a stop in Rome. (The flight is 8.5 hours from Toronto to Rome, and a little more than an hour from Rome to Catania.) From Catania, those who don't want to rent a car can take one of the frequent buses departing for Taormina, roughly an hour-long trip.

Where to eat

Da Cristina does not have table service, but it does have the best arancini in town – as well as pizza, cheese-filled sfoglie and other savoury treats. Via Strabone 2

Willy Wonka would have been comfortable in D'Amore, a pasticceria dishing out homemade sweets, including gelato and cannoli. Via C. Patricio 28;

La Capinera is one of Taormina's finest Michelin-starred restaurants, thanks to its inventive twists on Sicilian cuisine (such as squid-ink tagliolini pasta with yellowtail ragu) and top-notch service (including, in the warmer months, on the panoramic terrace). Via Nazionale 177

Where to stay

At the family-run Villa Costanza Bellavista, full apartments, located a quick but stair-filled walk from the Corso Umberto, include access to a pool and panoramic terrace overlooking the Mediterranean. The same owner also offers apartments in the heart of Taormina's centro storico. From 60 euros ($84) a night. Via Otto Geleng 40;

The boutique hotel Villa Carlotta combines old-world charm with modern comforts, and has great views and a restaurant. From 119 euros ($167) a night. Via Pirandello 81;

Formerly a noble palazzo, the Villa Taormina today is a four-star hotel located right in Taormina's centre, with amenities including a shuttle service to the beach. From 149 euros ($209) a night. Via Tommaso Fazzello 39;