South to Sicily

Oozing Italian chic, Milan is numero uno for fashion and design. Check out the latest styles and designer labels in the trendy fashion district of Quadrilatero d’Oro and stroll beside the Naviglio Grande canal to admire some medieval design. Don’t miss the vaulted glass shopping arcade of Galleria Vittorio Emanuele II – one of Milan’s must-see landmarks – or the imposing Duomo di Milano, Italy’s largest cathedral. You can take a lift up to the famous Rooftops of this extraordinary building, bristling with spires adorned with some 3,500 statues of saints and creatures. No visit to Milan is complete without visiting Santa Maria delle Grazie, home to Leonardo da Vinci’s mural, The Last Supper. Overnight Milan.

From Milan, sit back and relax on a five-hour rail journey south, weaving through the glorious countryside of Tuscany and on past Rome before arriving in Naples for a two-night stay. Historic sites in this chaotic yet fascinating city include Castel Nuovo (its ramparts offering views across the Bay of Naples to Mt Vesuvius), the Royal Palace of Palazzo Reale, the San Gennaro Catacombs and the peaceful garden-framed cloister of Santa Chiara. Delve into narrow streets like Spacconapoli to discover authentic pizzeria, cafés and shops selling masks, clay nativity scenes and pasta. Head to Caffé Gambrinus for the best gelato and pastries. Overnight Naples.

Join your private guide for a tour of Herculaneum, destroyed in the same eruption that sealed the fate of its more famous sister site, Pompeii. Buried under a deep pyroclastic flow, the buildings and mosaics at Herculaneum were better preserved than those at Pompeii. Walking around the compact grid of streets, you’ll gain a vivid sense of Roman life, abruptly snuffed out nearly two millennia ago. Highlights include the Hall of the Augustales (a meeting hall for the emperor’s priests) and the House of Neptune and Amphitrite (with its wine rack, wooden balcony and wall mosaics). In the afternoon, explore Pompeii with your private guide, who will explain what happened on that fateful day in AD79 when Vesuvius dumped 6m of pumice and ash on the town. You’ll be shown cart tracks preserved in streets, as well as everything from temples and theatres to baths, bakeries and brothels. In the evening, back in Naples, relax over a traditional Neapolitan meal, such as spaghetti alle vongole with clams, garlic and olive oil. Overnight Naples.

Depart Naples in the morning and continue your train journey south to the boot of Italy. Cross the narrow Strait of Messina to reach Sicily where your first four nights on the island are spent in the ancient coastal hill town of Taormina. Try out one of the many local restaurants, trattorias or pizzerias for a taste of Sicilian fare. Fresh fish, such as tuna, swordfish and sardines, are a good choice. Overnight Taormina.

On your first day based in Taormina, join a privately guided day trip to Mt Etna, a short drive away. Before continuing your rail journey around Sicily, you have another two full days to join in on some of the optional excursions and spend time exploring the town of Taormina. A popular tourist destination ever since it became established on the Grand Tour, Taormina was founded in the 4th century BC. Scooped out of the rocky hillside above the town, the remains of an ancient theatre command spectacular views of Naxos Bay and Mt Etna. Be sure to also track down the beautiful church of St Catherine of Alexandria – pretty in pink due to its marble façade – and stroll the narrow streets and alleyways of Porta Messina. Other highlights include the terraced gardens of Park Giovanni Colonna and the tiny island of Isola Bella, reached at low tide across a pebbly beach. Further two nights in Taormina.

A two-hour rail journey along the coast of the Ionian Sea brings you to the ancient city of Syracuse, a UNESCO World Heritage Site. One of the oldest cities in the Mediterranean, Syracuse’s Greek and Roman heritage is evident in its incredible collection of historical sites. Overnight Syracuse.

Rising out of the sparkling azure sea, the honey-stone buildings of Syracuse evoke a timeless beauty – especially on the island of Ortygia where the city’s ancient centre is graced with magnificent piazzas and iconic sights like the Temple of Apollo, Fountain of Arethusa and Cathedral of Syracuse. Spend your first day in Syracuse falling under the spell of what was once the largest city in the ancient world. Overnight Syracuse.

Meet your private guide for an equally spellbinding tour of Agrigento and the Valley of the Temples. Sicily’s archaeological heritage at its most astonishing, this World Heritage Site contains no fewer than eight temples, including the remarkably well-preserved Temple of Concordia, built in the 5th century BC. Overnight in Agrigento.

Take the two-hour train ride to Sicily’s capital, Palermo – a grandiose city renowned for its rich history, culture, art, music and gastronomy. For history buffs, it has everything from Romanesque and Gothic to Baroque and Art Nouveau styles flowing through a magnificent range of palaces, churches and monuments. Quirky highlights include one of Europe’s largest trees – a fine specimen of Moreton Bay fig in the city’s botanic gardens – and the grisly but intriguing Catacombs of the Capuchins where 8,000 well-dressed mummies adorn the walls. For an authentic Sicilian culinary experience, head to the food markets and try local capers, snails marinated in olive oil and thick pizza topped with onions and Caciocavallo cheese. Following two nights in Palermo.

Another day to explore this fascinating Sicilian capital.

In the afternoon, a one-hour rail journey follows the glittering coastline of the Tyrrhenian Sea before arriving in the beautiful medieval town of Cefalú. Golden-hued buildings cluster around a harbour packed with colourful fishing boats, while narrow cobbled streets wind between pretty piazzas and picture-postcard churches. Famed for its fine mosaics and soaring towers, the cathedral is Cefalú’s must-visit landmark, but it’s also well worth hiking up La Rocca (the town’s craggy 284m backdrop) for superb views and a chance to visit the ruins of the Temple of Diana. Overnight Cefalú.

With a full day to enjoy this exquisite town, there’s time to visit the Museo Mandralisca, enjoy the cool shade of the Lavatoio Medievale (an ancient wash house), bask on Cefalú’s perfect crescent of sand (one of Sicily’s best beaches) and relax in Piazza Garibaldi with a pistachio-flavoured ice cream. After dinner, take the overnight sleeper train to Rome. Alternatively, stay another night in Cefalú or Palermo before flying back to the UK the following day.

If you opted to take the sleeper train, you will arrive in Rome this morning. You can either extend your stay in the city, or change trains and continue your homeward rail journey north, weaving through the beautiful mountain scenery of northern Italy and Switzerland to arrive in Zurich by evening. Stretch your legs with a stroll along the River Limmat, soaking up the history and culture of the old town, where you will also find an excellent choice of restaurants and bars. Overnight Zurich.

The rail journey from Zurich to Paris takes just over four hours. Upon arrival in Gare de Lyon take the Paris PER to Gare du Nord where you have time for lunch or an afternoon snack before boarding the Eurostar back to London St Pancras.