Classic Cities of Italy

Smart, stylish and cosmopolitan, Milan is a head-turner – whether you’re browsing designer labels in the trendy fashion district of Quadrilatero d’Oro or gazing up at Leonardo da Vinci’s 15th-century mural The Last Supper, which graces the convent of Santa Maria delle Grazie. With a full day to explore the city, you will also have time to take in the ornate glass shopping arcade of Galleria Vittorio Emanuele II and the glorious Gothic pile of Duomo di Milano – the cathedral’s Rooftops adorned with no fewer than 135 spires, bristling with statues and gargoyles. Overnight Milan.

From Milan, travel south on a two-hour rail journey into Tuscany, watching the scenery change to classic Italian vistas of vineyard-draped hills, terracotta-roofed villages and cypress-studded fields. On arrival in Florence, check in to your hotel for the following three nights.

The historic centre of Florence is relatively compact and easy to explore on foot. With two full days to immerse yourself in its cultural treasures, you will be able to see many of the classic sights, enjoy the city’s romantic atmosphere and sample exquisite Florentine cuisine. Make a bee-line for the city’s symbolic Duomo –Santa Maria del Fiore – and climb to the top of the terracotta-tiled dome for 360-degree views. The Uffizi – Italy’s greatest art gallery – will also be high on your list. Botticelli’s The Birth of Venus can be found in its hallowed halls, as well as work by Bellini, Caravaggio, da Vinci, Raphael and Rembrandt. Head to Piazza della Signoria to see a copy of Michelangelo’s David (the original is in the Galleria dell’Accademia) and visit Michelangelo’s tomb in the beautifully cloistered church of Santa Croce. Walk across Ponte Vecchio (a medieval bridge containing jewellery shops); watch the sunset over the Arno River from Piazzale Michelangelo and shop for leather goods in Loggia del Mercato. Remember to look out for Il Porcellino – the Fountain of the Piglet. Rubbing its snout is meant to bring you luck! Both nights Florence.

Take the one-hour train journey south to the hilltop city of Arezzo for an overnight stay. A relaxed place to explore, Arezzo feels almost like an open-air museum with its Medici fortress, Roman amphitheatre, medieval streets and grand piazzas. Don’t miss Piero della Francesca’s 15th-century fresco (Legends of the True Cross) which describes the history of Christ’s Cross in exquisite detail. You can find it in the church of San Francesco on Piazza Grande – an atmospheric spot to admire medieval and Renaissance architecture from one of the pavement cafés. Explore the side streets to find restaurants offering Tuscan dishes rich in local cheeses, prosciutto, tomatoes and homemade pasta – refuelling you for an afternoon taking in some of Arezzo’s other sights – including the battlements of Fortezza Medicea. Overnight Arezzo.

Today’s hour-long train journey south takes you into the region of Umbria, skirting Lake Trasimeno, before arriving in Perugia where you spend the following two nights. Umbria’s old hill-top capital is riddled with narrow medieval streets and there’s also a museum containing prehistoric, Etruscan and Roman artefacts. Perugia is home to Baci – Italy’s famous sweet treat of hazelnut and dark chocolate wrapped in poetic love notes. Overnight Perugia.

With two nights in Perugia, you could divide your time between exploring the city – visiting sights such as Fontana Maggiore and the Oratorio di San Bernardino – and taking an optional trip to nearby Assisi. Burial place of St Francis, the Basilica di San Francesco dates from 1228 and contains Lorenzetti’s and Giotto’s famous frescoes depicting the saint’s life. The honey-hued cathedral complex is not only a breathtaking sight, but offers stunning views across the Umbrian countryside. Overnight Perugia.

Departing Perugia, your train winds south through Umbria, passing the charming hill town of Spoleto before arriving in Rome (a 2.5-hour journey). The ‘Eternal City’ requires little introduction, but whether you are a seasoned visitor, or this is your first trip to the Italian capital, there is always plenty to see and do. Following three nights in Rome.

Explore the imposing Colosseum and imagine the roar of the 70,000-strong crowd as warriors, slaves and wild beasts engaged in deadly combat nearly 2,000 years ago. Ancient Rome is also vividly portrayed in the nearby Roman Forum, a patchwork of ruined triumphal arches, basilicas and temples that once formed the city’s ceremonial and civic heart. Located close to Piazza Navona (a beautiful square line with palaces and pavement cafés with three flamboyant Baroque fountains at its heart), the Pantheon – one of Rome’s best-preserved ancient buildings – is also well worth a visit. Other highlights include scaling the elegant Spanish Steps to the church of Trinitá dei Monti, admiring famous sculptures (like the Dying Galatian) in Musei Capitolini and tossing a coin into Trevi Fountain, to guarantee your return to Rome! What it lacks in size, the 43-hectare Vatican City – an independent state within Rome – more than makes up for with its historical, cultural and religious esteem. The vast papal audience ground of St Peter’s Square is flanked by the 284 columns of Bernini’s Colonnade, dwarfed by the façade of the world’s largest church. Entering the Basilica of St Peter, the sheer size and splendour of the building leaves you in awe. Admire the vast, yet intricate dome and other works of art by Michelangelo, such as the emotive sculpture, Pieta. The art inside the Vatican Museums is equally astonishing – a treasure store of Ancient Egyptian bas-reliefs, Roman and Greek statues, medieval altarpieces and Renaissance masterpieces. Following the museum trail through beautiful rooms, frescoed by artists like Raphael and Pinturicchio, you reach the most breathtaking room of all, the Sistine Chapel, with its glorious ceiling of Biblical art painted by Michelangelo between 1508 and 1512. Both nights Rome.

Depart Rome and travel by train, via Bologna, to Venice, a journey of around four hours. A truly unique place, Venice endures against all the odds – a city built on mudbanks where streets – some water, some stone – are lined by grand old palaces and fine churches. Even if you’ve been before, Venice will enthral you. Spend the next two nights in Venice.

Venice is easy to explore on foot – or sit back and relax in a gondola, drifting along the canals and admiring the lavish Venetian architecture. Alternatively choose a private guide to lead you to the historical sites that the city is so famous for. Walk across the magnificent marble bridge of Ponte di Rialto, admire the Campanile bell tower and imposing Palazzo Ducale in Piazza San Marco and visit the Byzantine Basilica St Marco, renowned for its 11th-century golden mosaics. Venice also offers rich picking for eating out and shopping. Track down fruit and vegetable stalls and gourmet food shops along the Grand Canal and treat yourself to local Murano glassware or a traditional Carnival mask. Overnight Venice.

Continuing to Zurich, via Milan, today’s 6.5-hour train journey passes through some of Europe’s most beautiful mountain and lake scenery. In Zürich, 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 in Zurich. Alternatively travel back on the magnificent Venice Simplon-Orient-Express.

The rail journey from Zurich to Paris takes just over four hours. Upon arrival in Gare du 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.