Palermo, to put it charitably, is an acquired taste. Incredibly, parts of the capital remain unrepaired from bomb damage suffered in World War II, and this long-term neglect reflects the city’s overall air of abject poverty and dilapidation. The imposing Cathedral, baroque churches and ornate Cappella Palatina in the Palazzo dei Normanni are the highlights for visitors, but because of the maze of traffic-clogged side streets in the historic center, we strongly suggest hiring a private driver-guide through your hotel concierge.
Taormina is another matter entirely. Sicily’s shining star, the town nestles atop a wonderfully panoramic rocky eminence 500 feet above the Ionian Sea, almost directly beneath Mount Etna. Lovely medieval buildings, fountain-dotted piazzas and luxuriant subtropical gardens lace the pretty town, its engaging pedestrian-only promenade (Corso Umberto I) lined with cafés and boutiques. Not to be missed is Teatro Greco, the well-preserved remains of the great terraced Greco-Roman theater still used today as as the setting for a summer arts festival.
Two hours southward along the coast lies Syracuse, a city that once rivaled Athens at the height of its glory and was later the birthplace of the renowned mathematician Archimedes. Ignore the nondescript industrial suburbs and persevere toward the sea and the more pleasant historic zone sheltering the stately ruins of a Greek theater; your tranquil base for exploration is the island of Ortygia, connected to the mainland by two bridges. Baroque buildings and medieval palazzos hug shady, narrow streets that abruptly open out into fetching sunlit piazzas. Among the chief sights: the 18th-century Cathedral (built over the remains of a temple to Athens resurrected in the sixth century B.C.) and the Galleria Regionale (housed in a 13th-century palace containing works such as Antonello da Messina’s “Annunciation” and Caravaggio’s “Burial of St. Lucy”).
Along the southern coast, the ancient settlement of Ragusa is a mixed experience: The zoning-be-damned new part of town welcomes visitors with a ring of oil refineries, but the atmospheric old part of town (“Ragusa Ibla”) caps a dramatic separate hilltop and merits an overnight. A harmonious assemblage of baroque buildings lines the enclave’s medieval labyrinth of narrow streets, along with inviting shops selling local ceramics, wines and premium olive oils.
The west coast of Sicily is an unrelenting and grossly polluted industrial wasteland of no conceivable interest to visitors. Even the celebrated classical ruins of Agrigento have been disfigured by uncontrolled tourism, with the adjacent city being little more than a grim pile of concrete. Our recommendation to those contemplating a visit to Sicily: Concentrate on the east coast in Taormina and Syracuse, and above all, enjoy a few nights at the Grand Hotel Timeo in the former.
Belmond Grand Hotel Timeo
Spectacular 1873 resort hotel with views to the Mediterranean and Mount Etna, set in terraced gardens filled with jasmine, vines, citrus trees, cypresses and urns of scarlet geraniums.
Hotel Villa Ducale
Intimate and stylish 11-room, six-suite boutique hotel in the romantic resort town of Taormina, offering stunning views of Mount Etna and the Mediterranean coastline.
Rocco Forte Verdura Golf & Spa Resort
Admirable 203-room property on beautifully landscaped 560-acre seafront site, 60 miles south of Palermo. Stylish, nicely furnished rooms and villas offer views of the Mediterranean.