This glorious, glamorous town sits perched high above the Mediterranean, with stunning views of Etna in the distance and an impressive culinary and nightlife scene. Taormina has been a destination for Europe’s elite since it was fashionable to take a ‘Grand Tour’ of Europe in the 19th century, with luxury hotels opening up to cater to these early high-end travellers.

Visitors have flocked here since the mid-1800s to take in theatre and operatic performances in the ancient Greek amphitheatre, perched on the cliff-side with its breathtaking view of sea and volcano, and to dine and drink and dance in the town’s grand hotels: the most famous of them all, the Belmond Grand Hotel Timeo. 

Taormina’s roll call of famous visitors through the centuries is nothing short of dazzling- Goethe, Alexander Dumas, Oscar Wilde, Johannes Brahms, DH Lawrence, Capote, Cary Grant, and Greta Garbo are just a few of those who fell in love with the town’s charms in days gone by. Today, Taormina’s amphitheatre hosts the glittering Taormina Film Festival in June as part of its summer-long Taormina Arte culture fest, with Robert de Niro and Colin Firth just a few Hollywood stars to walk the red carpet.

The town’s winding medieval streets are lined with designer boutiques, bars and restaurants, with each bend in the lane providing yet another heart-stopping view. For dining, Principe Cerami is the 2 Michelin star highlight for a meal, while the one-star La Capinera has a famously good tasting menu with a focus on Sicilian cuisine done in innovative ways.

A walk through Taormina is a walk through history, with the stunning Palazzo Corvaja a dizzying mix of Arab, Norman and Gothic architecture, while the Piazza del Duomo has a splendid 13th century Baroque cathedral.

The ancient city of Catania sits at the foot of Mount Etna, on the shores of the Ionian Sea. Etna has shaped the history and the architecture of this city, with each tragic catastrophe creating a new era of city design. The huge volcanic eruption and later earthquake of the 1700’s led to a baroque re-creation of the old town, with wide avenues and spacious piazzas, all created in grey lava rock from Etna’s explosions. The people of Catania know how to begin again with what they have, and have a healthy respect for ‘La Muntagna’ which smoulders above, occasionally sending perfect smoke rings into the sky.

In Catania’s Piazza Duomo, visit the Cathedral, re-built on an earlier foundation of Roman baths and columns, the lava elephant fountain, or wander the nearby fish market, observing a way of Sicilian life that has not changed in centuries. You can also see the three Greek theatres in the ancient quarter which have survived the volcano’s fury for millennia, take in an opera performance at the Teatro Massimo Bellini, or visit the Museo Belliano, also dedicated to the Catanian composer, Vincenzo Bellini.

The gardens and orchards surrounding Catania are bursting with lemons, oranges and vibrant vegetables, while the vineyards of Etna’s slopes produce wines that are gaining notoriety in Europe, with spicy, deep reds and dry, high altitude whites. The reds are commonly known as the ‘Burgundy of the Mediterranean’, and vineyards producing top drops include Passopisciaro, Graci, and Fessina. If you don’t have time to visit any vineyards, the enoteca Wine and Charme in Catania is an absolute delight, showcasing the best Etna wine as well as delicacies from across Sicily- capers, Modico chocolate, pistachios, cured meats, cheeses, and olive oils.

All of this excellent produce as well as an abundance of seafood finds its way to Catania’s restaurant tables. For pizza, go no further than Cutilisci; for seafood, Osteria Antica Marina by the fish market is a standout. For cannoli— that delicious, creamy ricotta stuffed pastry—head to Savia. While in Catania, it is near-compulsory to try the Sicilian staple, Pasta alla Norma, which originated here and is a deliciously simple combination of fresh pasta, eggplant, ricotta, basil and a rich tomato sauce. Trattoria del Forestiero is known as serving up the best, but there’s some stiff competition.

Mount Etna itself is situated in a beautiful national park with some stunning walking trails– where the volcano rises above the trees and you walk through an ever-changing landscape of lemon groves and vineyards, up to beech and oak forests and finally across dark lava beds as you move higher.

Cefalu is an enchantingly pretty medieval seaside town with a superb Byzantine cathedral erected by the Norman king, Roger II, and a lovely stretch of beach. The walled medieval town was made famous in the 1998 film Cinema Paradiso, but the real highlight is the cathedral with astonishing mosaics, particularly the apse mosaic of Christ Pantocator, which is considered perhaps the finest Byzantine image in all of Italy.

On a yacht charter in Cefalu, you can hike up the imposing La Rocca above the town to see a megalithic temple and superb views, or stay in town to visit Lavatoio, the Saracen wash-house or the ruins of the 13th century medieval palace, Osterio Magno. The Madralisca Museum is also a highlight of Cefalu for visitors, while the town itself is wonderful for exploring with its jumble of Greek, Italian, and Arabic architectural influences.

If you’re in the mood for a seafood lunch, head to Ostaria del Duomo in front of the cathedral for the simply unforgettable carpaccio di pesce, a medley of wafer-thin sardines, anchovies, prawns and whitefish dressed in local olive oil and lemon juice. Afterwards, stroll along the waterfront eating gelato, looking out at the colourful fishing boats bobbing in the clear emerald waters.

Stunning, World Heritage-listed Syracuse is one of the dazzling highlights of a Sicily yacht charter. The walled city of Syracuse abounds in ancient ruins, baroque piazzas, and quiet olive groves. In Ortigia, the atmospheric old quarter located on a narrow isthmus, you’ll find glamorous wine bars and designer boutiques alongside old fishermen mending their nets by the sea.

Once the largest city in the ancient world and later the birthplace of Archimedes, Syracuse’s crowning glory is the Temple of Athena, one of the great spectacles of Sicily. This ancient Doric Greek temple is still in use, after being converted into a Christian church in the 600s, a mosque during Islamic rule in the Dark Ages, and it is now a Roman Catholic cathedral.

The fantastic Archeological Park Neapolis includes a Roman amphitheatre and a Greek theatre, where plays are performed in the summer months. There’s also a limestone cave called Orrechio di Dionisio, the acoustics creating a whispering gallery- one of Caravaggio’s old haunts. For archaeology enthusiasts, the Museo Paolo Orsi is perhaps the best museum of its kind in all of Italy, while the church of Basilica Santuario della Madonna delle Lacrime is a spectacular modern edifice rising above the town.

For dinner, the smartest table in town is at the Regina Lucia in Piazza Duomo, while Oinos is also excellent. For more rustic food, head to the Osteria Da Mariano, where the cucina povera is heartily celebrated with local dishes like pistachio dusted ricotta, and parmesan cheese for pasta is replaced with a sprinkling of ground almonds. To indulge in some Sicilian wine, the Enoteca Solaria near the Piazza Duomo cannot fail to impress.

It may be difficult to drag yourself away from the spectacular Sicilian coastline, but Ragusa is utterly worth the trip. Sprawled atop two hilltops, in a tortured, beautiful landscape of valleys and ravines, this is a city of two hearts: one modern, one baroque, with the new town built after an earthquake prompted a new beginning (an old story in this region). When it came time to move to the new town, the old inhabitants couldn’t bear to leave, so built their houses on the ruins of the old town, creating the twin townships of Ragusa.

The old town, Ragusa Ibla, is a wonderful network of laneways and cafes, artist studios and fine restaurants with highlights including the Michelin starred Ciccio Sultano and Ristorante La Fenice. This is where the hit show Inspector Montalbano is filmed.

As for the newer, upper town of Ragusa Superiore, it’s still worth a visit – if not just for the view of the old town on the next hilltop. There’s also a very good archaeology museum, and just outside town is the Castella di Donnafugata, a grand, pseudo-gothic country villa with splendid gardens and country walks.

Sicily was the site of one of the greatest flowerings of ancient Greek culture, with so many Greek colonies set up in the 8th century BC that the area came to be known as part of ‘Magna Greca’: Greater Greece. Sicily consequently has some of the finest surviving Doric temples and amphitheatres to be found on earth- and Agrigento is an archaeological treasure trove, with 10 such temples in varying stages of crumbling. The Temple of Concordia, the Temple of Olympian Zeus, and the Temple of Hera are the most noteworthy. Agrigento is a superb destination for those with an interest in the classical world of the Ancient Greeks.

Cruising up the coast a bit further you’ll find Selinunte, where the Temple of Hera, wife of Zeus and Goddess of Marriage, stands right on the edge of the coast above the sea. You can anchor your charter yacht right below the temple in the waters of the ancient port, and come up to explore this and the other temples, which are generally a great deal less crowded than those at Agrigento. Due to the seaside temple setting, this is a very special place to come at sunset.