Classic Cities of Italy

Classic Cities of Italy

from £1,958 excluding flights

  • 14 nights
  • Year round
  • Multi-destination
  • Rail
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italy historic town of assisi umbria istk

Classic Cities of Italy

from £1,958 excluding flights

  • 14 nights
  • Year round
  • Multi-destination
  • Rail

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Highlights

In pictures
italy duomo santa maria del fiore florence istk

Gaze across the rooftops of Florence from the top of the Duomo

italy florence uffizi gallery courtyard astk

Admire the paintings of Renaissance masters in the Uffizi

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Lose yourself in the medieval streets of Arezzo and Perugia

italy early morning at the colosseum rome istk

Discover the magnificent ancient wonders of Rome

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Stroll through the breathtaking galleries of the Vatican Museums

italy grand canal gondolier venice istk

Experience the truly unique city of Venice

Why this trip...

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On track and flight free

Slow travel from London to the classic towns and cities of Europe with your rail tickets and accommodation taken care of

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Euro culture

Experience a wealth of history and heritage exploring the fascinating heart of Europe

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Carefully planned

This itinerary has been thoughtfully designed to provide the experiences and places you'll enjoy at a comfortable pace

Overview

This is the ultimate Italian city break, but instead of snatching a whirlwind weekend away in Rome or Venice, you have two whole weeks of slow travel – winding through France and the Alps by train, then joining the dots between Italy’s most beautiful and iconic cities. Travelling in comfort, watching the countryside of Tuscany, Umbria, Abruzzo and Le Marche pass by, the excitement builds as your train approaches each stop on this ‘grand rail tour’. The first stage is from London, via Paris, to Milan, where you have a couple of nights to soak up the city’s style and culture before continuing south to Tuscany.

Tuscany: Florence and Arezzo

The glorious sights of Renaissance Florence await, with two full days to fall under the spell of the terracotta-tiled duomo and seek out Botticelli, da Vinci, Michelangelo and other masters in the head-spinning galleries of the Uffizi. Weaving past vineyards, cypress-studded hills and terracotta villages, the next stop on your rail journey is the Tuscan hilltop town of Arezzo. A wealth of fortresses, churches, museums and monuments are waiting to be explored here (including one of Italy’s greatest frescoes – the Legend of the True Cross), but this is also one of Tuscany’s less-visited destinations, offering an authentic insight into the region.

Umbria: Perugia and Assisi

Continuing south into Umbria, the hill town of Perugia sits in the ‘Green Heart of Italy’, its fine old churches and cathedral rising above a tangle of medieval streets. Prehistoric, Etruscan and Roman artefacts can be found in its excellent museum, while the crenelated, 13th-century Palazzo dei Priori is one of Umbria’s most impressive buildings. Easily visited on an optional side trip during your stay in Perugia, the magnificent town of Assisi is dominated by the revered Basilica di San Francesco – shrine of St Francis.

Rome and Vatican City

Travelling by rail through Umbria and into Lazio, you reach Rome, where three nights allows you to explore all the classic sights of the Italian capital – from the Colosseum and Roman Forum to the Pantheon and Trevi Fountain. A city within a city, the Vatican deserves one of your days: climb high in to the dome of the Basilica of St Peter for views across the rooftops of Rome and lose yourself in the immense art treasury of the Vatican Museums as you track down Michelangelo’s breathtaking mural on the ceiling of the Sistine Chapel. Cultural clout aside, Rome also has a lighter side… linger over lunch in a trattoria or pizzeria tucked down a side street, or simply watch the world go by while you gorge on gelato in the wide-open expanse of Piazza Navona.

Venice

To avoid anti-climax, there’s only one place to head for after Rome – and that’s Venice. Travelling by train, via Bologna, you reach the romantic city of canals, piazzas and palazzos in around four hours. Easy to explore on foot or by gondola, Venice is a fitting climax to your rail tour of Italy’s classic towns and cities. Rising like a giant exclamation mark in Piazza San Marco, the 98.5m-tall Campanile towers above Palazzo Ducale (the Doge’s Palace). A warren of streets leads you to Ponte di Rialto (with its dreamy views of the Grand Canal), the Accademia (a treasure store of Venetian masterpieces) and the fine Baroque church of Santa Maria della Salute. Plenty to reflect upon during your homeward rail journey, via Zurich and Paris or perhaps indulge on the magnificent Venice Simplon-Orient-Express.

Itinerary

Day 1 London - Milan

Depart London in the morning and travel by Eurostar to Paris Gare du Nord. Transfer to Gare du Lyon in time for lunch before embarking on your journey to Milan. Following two nights in Milan.

Depart London in the morning and travel by Eurostar to Paris Gare du Nord. Transfer to Gare du Lyon in time for lunch before embarking on your journey to Milan. Following two nights in Milan.

Day 2 Milan

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.

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.

Day 3 Milan - Florence

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.

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.

Days 4-5 Florence

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.

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.

Day 6 Florence - Arezzo

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.

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.

Day 7 Arezzo - Perugia

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.

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.

Day 8 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.

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.

Day 9 Perugia - Rome

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.

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.

Days 10-11 Rome and Vatican City

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.

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.

Day 12 Rome - Venice

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.

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.

Day 13 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.

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.

Day 14 Venice to Zurich

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.

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.

Day 15 Zurich - London, via Paris

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.

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.

Accommodation Options

We will recommend accommodation for this holiday, but with a vast choice available, we can adapt to suit your personal preference mixing different grades and styles in different cities.

Discuss your options with our Travel Specialists.

Venice Simplon Orient Express

orient express in station train guards

An alternative option for your return is to travel overnight from Venice to London on the luxurious Venice Simplon Orient Express. The ultimate in romantic rail travel, it includes a dedicated steward service, fine dining and all the glamour and razzmatazz of the elegant dining carriages and art-deco 1920s cabins.

Prices and Departures

Price from £1,958 excluding flights

This itinerary is based on rail travel from the UK, so flights are not required.

What's Included

  • Accommodation in rooms with private bathroom
  • Breakfast throughout
  • All rail journeys
  • All compulsory seat reservation fees on high-speed and international trains
  • 24 hour emergency assistance from our team during your holiday
  • No surcharge guarantee
  • Full financial protection

From prices per person

Based on two sharing a twin room with private facilities and breakfast. Prices may vary depending on departure date. Please contact us for a detailed quote based on your preferred travel dates.

Departure Duration Twin Price
Year Round 14 nights £1,958 Round trip by rail
Year Round 13 nights £1,698 Fly back on Day 14 - price excludes flights*

*Please note that flights are not included in the price, but will be quoted at the time of booking.

This itinerary is flexible and the number of nights at each of the overnight stays can be extended or reduced.

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nordic team eric shadbolt bw
One of our specialists
Meet Eric

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