Inspiration for your own tailor-made trip

From Buzzing Cities to Golden Coastlines An Italian Rail Adventure from North to South

Italy – Milan – Rome – Sicily – Florence – Bologna – Verona

Starting from between £5670 to £7500 per person for 25 days depending on the season of travel, advance booking time and the accommodation and activities chosen

Itinerary Highlights

  • Embark on this epic 25-day train journey through Italy, city-hopping from the Alps to Sicily and back
  • Immerse yourself in Italy’s rich history and culture with private walking tours in cities like Milan, Rome, Palermo, Florence and Verona
  • Savour island life on the Mediterranean as you spend six days road-tripping around sumptuous Sicily
  • Benefit from our Original Services: expert guides, local Concierges, 100% carbon absorption and more
From glassy Alpine lakes to sumptuous Sicilian coves and crumbling Roman ruins to swanky art-deco neighbourhoods, this great Italian rail journey is infused with history, culture and scenic beauty at every turn.

After wiggling your way through France by train – and spending a night in Paris en route – your first port of call is the fashion-forward city of Milan, where you’ll get your first taste of Italy’s renowned Renaissance architecture on a visit to the Duomo Cathedral. Next up is a city that needs no introduction: the captivating capital of Rome. Spend four days discovering world-renowned ancient sites, palatial residences and the marvels of Vatican City before hopping on a southbound sleeper train.

The second chapter of this adventure takes place on the sun-drenched Mediterranean island of Sicily. After soaking in the eclectic sites of Palermo, spend six days winding your way around the island in a hire car, between golden Baroque cities, luscious countryside and the peaceful coves of the Ionian Sea.

Your final ten days in Italy are all about experiencing the cosmopolitan jewels of the north. Learn about the birth of Renaissance art in Florence, eat celebrated culinary delights in Bologna and bask in the Shakespearean charms of Verona. Round off your adventure with a foray into Switzerland as you spend a day exploring the colourful lakeside city of Zurich, before either flying or catching the train home.
Lake Leman © Hotel Mirador & Spa
Lake Leman © Hotel Mirador & Spa
Train © Julie GUICHES  / PINK / saif images
Train © Julie GUICHES / PINK / saif images
Milan - Lombardy - Italy © Jerôme Galland
Milan - Lombardy - Italy © Jerôme Galland
Milan - Lombardy - Italy © Jerôme Galland
Milan - Lombardy - Italy © Jerôme Galland
Milan -Italy © Faustine Poidevin
Milan -Italy © Faustine Poidevin
Milan - Lombardy - Italy © Jerôme Galland
Milan - Lombardy - Italy © Jerôme Galland
Rome - Italy © Jérôme Galland
Rome - Italy © Jérôme Galland
Rome - Italy © Pauline Chardin
Rome - Italy © Pauline Chardin
Sicily - Italy © Sabine Bungert/LAIF-REA
Sicily - Italy © Sabine Bungert/LAIF-REA
Sicily © Fotolia
Sicily © Fotolia
Florence - Italy © Rhiannon Taylor
Florence - Italy © Rhiannon Taylor
Cannoli - Italy © ablokhin/stock.adobe.com
Cannoli - Italy © ablokhin/stock.adobe.com
Florence - Tuscany - Italy © Guenter Standl/LAIF-REA
Florence - Tuscany - Italy © Guenter Standl/LAIF-REA
Train © Phanvan Masanobu Thaibihn / Pexels.com
Train © Phanvan Masanobu Thaibihn / Pexels.com
Train © Philip Nix / Gallery Stock
Train © Philip Nix / Gallery Stock

Itinerary

100% customisable for you

Your rail adventure begins in London this morning as you glide beneath the Channel aboard the Eurostar, leaving the bustle of the UK behind and arriving in Paris by early afternoon – a journey of around two hours and fifteen minutes.

The remainder of the day is yours to enjoy in the French capital. Settle into your hotel, wander nearby boulevards or linger over an unhurried dinner as the ‘City of Lights’ comes alive. This relaxed introduction sets the tone for the remarkable journey ahead. Bon voyage...

Wake up in Paris and enjoy a relaxed morning in the city, perhaps with a café au lait and a stroll along nearby streets as the capital eases into the day.

In the late morning, make your way to Gare de Lyon station to board your train bound for Italy. The seven-hour journey whisks you south through the French countryside and onward towards the Alps, where mountains, tunnels and valleys mark your gradual transition into a new landscape and across the border into Italy.

By early evening, you’ll arrive into Milan, the stylish capital of Lombardy. On arrival, check in for a two-night stay at an elegant hotel in the heart of the Centro Storico, just moments from the energy of Piazza del Duomo. Spend the rest of the evening settling into your Italian surroundings, perhaps with a leisurely passeggiata or a first taste of Milanese cuisine.

Rise and shine, it’s your first full day on Italian soil and there’s not a moment to waste. After a relaxing morning, head out for a private tour of Milan in the company of a knowledgeable local guide. Stroll from your hotel to the nearby Duomo Cathedral, one of the city’s most famous landmarks. The exterior of the building is a masterpiece, with its delicate stone lacework, intricate carvings and towering spires. After exploring the cultural and religious offerings inside, head to the roof for breathtaking views across the city.

Next up, is the Galleria Vittoria Emmanuele II, which is named after the first King of Italy and is the nation’s oldest (and fittingly regal-looking) active shopping gallery. Take your time browsing the luxury stores spread across this four-storey double arcade. Finish up with a tour of the Teatro Alla Scala, a beautiful theatre that counts itself among the three most prestigious opera houses in Italy.

After a morning spent soaking in the city, why not spend this afternoon visiting one of Milan’s hidden gems? Located just a few miles from the city is the Chartreuse de Pavie, an exceptional monastery complex that pays homage to the Lombard Renaissance with its flamboyant carvings of saints and Roman emperors.

Make your way back to the train station to embark on the next leg of your journey: a three-and-a-half-hour ride through Tuscany’s rolling hills and vineyards, ending in Rome. While it might be tempting to jump off the train when you pull into Florence and Bologna, hold steady, as you’ll be looping back here later on. A private driver will be waiting for you on arrival in the capital to whisk you off to your next hotel: an elegant, centrally-located property that is yours to call home for the next three nights.

Spend the rest of today letting your senses run wild in your new bustling surroundings – tuck into some local pizza and gelato, enjoy sunset from the banks of the Tiber or let your ears guide you to some live music across the river in Trastevere.

Get ready to step foot in the third country of the trip as you head into the heart of the Vatican City. Your private guide will lead you through a succession of this city-state’s marvels, from the awe-inspiring artworks of the Sistine Chapel to the site's museums, which contain impressive collections painstakingly assembled by popes over the centuries.

The rest of the day is yours to play with. Spend the afternoon drifting through Rome’s more contemporary rhythms: browse the boutiques of Campo de’ Fiori and Via del Governo Vecchio, pause for a long lunch or aperitivo in Trastevere, or wander along the Tiber as the city softens into evening. As dusk settles, grab a relaxed dinner in a neighborhood trattoria to get a taste of modern Roman life before tomorrow’s immersion into the ancient past.

Today, soak up a millennium of history with a guided tour of Ancient Rome. Begin with the Roman Forum, located on low ground between the Palatine and Capitoline hills. Here you’ll find the remains of Ancient Rome’s monumental centre, the site of religious, political and social activities, from triumphal processions to public speeches and elections.

The remains of the Baths of Caracalla, the city's second-largest Roman public baths, are up next, followed by the Via Appia Antica, one of Rome’s oldest roads, and the Arch of Constantine, a triumphal piece of architecture dedicated to the emperor Constantine the Great. Round off the tour at the Colosseum, an archaeological icon and one of the New Seven Wonders of the World.

Round off your few days in Rome with a day spent meandering through the centuries-old villas and grand religious establishments of Aventi, a luxurious residential district. Built into the hillside of the southernmost of Rome’s famed ‘seven hills’, this charming district offers an abundance of romantic parks and gardens, which are suspended above the river and exude beauty at every twist and turn.

Later this evening, you’ll be collected and privately transferred to your sleeper train bound for Palermo. The 13-hour rail journey touches on the old-school romance of train travel, with private sleeping compartments and inspiring views. When it comes to crossing the sea, the train is loaded onto a ferry, before continuing its journey through Sicily. If you’d rather a speedier journey, there’s the option to catch a one-hour direct flight from Rome to Palermo instead.

Open your eyes this morning to a different view of Italy: the idyllic coastal landscapes of Sicily. On arrival in Palermo, a private driver will be waiting to collect you from the station and transport you to a beautiful hotel in the historic centre, where you’ll be hanging up your hat for the next two nights.

The rest of today is yours to spend settling into the laid-back rhythm of island life. We recommend turning to our coveted destination-specific Dossier, which is full of our top picks for cafes, bars and restaurants in the area. One of our favourite spots in the city is the legendary Ballaro market, where you can drink in the colours and scents of local produce and culinary specialities.

On today’s agenda: a private walking tour of Palermo – the perfect introduction to this diverse and eclectic city and its charming network of bustling markets, romantic plazas and terraced cafes.

The rest of today is then yours to spend as you please. You can continue discovering the city at your own pace or embark on a gourmet stroll through our favourite Palermitan markets with a clued-up local guide.

Wave goodbye to the hustle and bustle of Palermo as you hit the road on an island-hopping road trip. This morning, you’ll be collected and privately transferred to a local rental agency, where you’ll collect a spacious and comfortable hire car ready for a few days of exploring the Sicilian lands. Your first destination is Agrigento, a serene hilltop city on the south coast of the island known for its rich collection of ancient temples.

The drive takes around two hours, but what’s the rush? We recommend making the most of your hire car to wind your way around the west coast, making stops at points of interest along the way. There’s the cloister and abbey of Monréale, the temple and theatre of Segesta and the hilltop citadel of Erice. Make sure to stop for a refreshing dip in the small seaside resort of Porto Palo, as well as a spot of ceramics shopping in the culturally renowned town of Sciacca. This is also a great opportunity to take a detour to Mazara del Vallo, a town steeped in religious and cultural heritage. We can arrange for you to explore this delightful seaside settlement with a local guide.

On arrival in Agrigento, check in to your beautiful hotel, surrounded by gardens, and spend the rest of this evening enjoying some much-earned R&R.

Today, you’ll be armed with queue-jumping tickets for the Valley of the Temples, a rich archeological park that houses the island’s best-preserved Greek temple. Agrigento was one of the main Mediterranean cities during the golden age of Ancient Greece. Magnificent Doric temples still stand strong today, made even more beautiful by the surrounding landscapes of rolling fields and fragrant orchards.

This afternoon, continue east to Noto, a classic Sicilian city bathed in golden Baroque architecture. The journey along the southeast coast takes around three hours, however we recommend making stops along the way at Ragusa and Modica, two cities rebuilt in the purest Sicilian Baroque style after the devastating earthquake of 1693.

Spend the rest of today settling into your charming new hotel: an elegant property located near Noto’s small port.

Wake up bright and early and make the most of your one full day in Noto, exploring the delightful city with a local guide. After falling victim to the great earthquake of 1693, Noto took the opportunity to rebuild itself in style, becoming a jewel of Baroque town planning. The historic centre has around 20 churches and ten palaces, which radiate around the main street of Corso Vittoria Emanuele, and myriad serene plazas. Take the opportunity to step into one of these fabulous palaces in the company of your guide, who will explain the history and cultural significance of the site.

Swap the grand architecture of Noto for the charms of the Sicilian countryside as you travel 30 minutes to Syracuse, a charming city bordered by rolling farmlands and the Ionian Sea.

Your home for the next two nights is a historic agricultural estate surrounded by whimsical gardens. Spend this evening kicking back and relaxing ready for a day of exploring the city tomorrow.

After a hearty breakfast at your hotel this morning, you’ll be met by a friendly local guide for a half-day tour of historic Syracuse. Founded in the 18th century by Greek colonists, the city remained the capital of Sicily throughout the Roman era. Vestiges of its flourishing past are concentrated on the island of Ortygia, the spiritual and historic heart of the city, and in the archaeological park of Neapolis, which features a Greek theatre, Roman amphitheatre and ancient stone quarries.

After immersing yourself in Sicily’s ancient foundations yesterday, today can be spent at your own pace. Enjoy a leisurely, self-guided day to savour island life, whether that means wandering Syracuse’s atmospheric streets, strolling along the seaside promenade or simply pausing for a quiet moment inside one of the city’s many churches. If the mood strikes, settle into a long lunch or seek out a final swim at a nearby beach before saying arrivederci to Sicily.

Later in the afternoon, drive to Catania to return your car, then continue your onward journey back to Rome. You can choose to board the 11-hour overnight sleeper train for a nostalgic rail experience across Italy, or opt for a short direct flight (just over one hour), arriving refreshed and ready for the next chapter of your trip.

Rise and shine as you pull back into the vibrant capital of Rome. Later today, you’ll catch the train to Florence, but first, there’s another side of Rome waiting to be uncovered.

While your first stop in Rome was all about basking in the city’s ancient glory, today is about savouring its contemporary highlights. Contrary to its image as a capital laden with millennia-old remains, Rome has garnered a more recent reputation for hosting avant-garde constructions designed by the greatest minds of this century. Zaha Hadid's MAXXI Museum, Renzo Piano's Music Park and Richard Meier's Ara Pacis are just a few of the modern masterpieces that prove the ‘Eternal City’ has stepped into the 21st century.

Later in the afternoon, head to the train station to catch the 90-minute train to Florence, your base for the next four nights.

Make the most of your first day in Florence with a private walking tour in the company of a local guide. After welcoming the greatest artists of its time (Dante, Michelangelo, Boticelli…), Florence gave birth to an exceptional cultural movement: the Renaissance. The result is an extraordinary ensemble of squares, palaces and churches, the majority of which are UNESCO listed.

The next two days are yours to spend soaking in the scenic and cultural delights of Florence at your own pace. You’ll be armed with queue-jumping tickets for the Uffizi Gallery, a grand museum located just off the bustling Piazza della Signoria that houses some of the finest works of the Renaissance. Fra Angelico, Filippo Lippi, Piero della Francesca, Paolo Uccello and Raphael are among the masters that take you on a journey through time, from the Middle Ages to the Baroque period. Beyond the historic centre, we recommend taking the time to hop across the River Arno to explore the Oltrarno district, an effortlessly cool neighbourhood which has managed to stay below the tourist radar.

Head back to the station this morning and embark on a short train ride to Bologna, the capital of Emilia-Romagna. Meet your private driver at the station and travel to your next hotel: a small and charming property in the heart of the historic centre. The rest of today is yours to settle into your new surroundings. We recommend taking a stroll through the nearby Piazza Maggiore, the city's main square, for an indulgent aperitif at one of the many terraced bars.

On today’s agenda: a private walking tour of Bologna, a beautiful city that has inherited not one, not two, but three nicknames, each of which pays homage to its history and soul. First, ‘La Dotta’ (‘The Learned’), which refers to the almost 1,000-year-old University of Bologna; second, ‘La Grassa’ (‘The Fat’), for its delicious culinary specialities, including the namesake Bolognese sauce; and finally, ‘La Rossa’ (‘The Red’), a name that evokes the crimson hue of the terracotta-tiled roofs of the city.

Your guide will delve deeper into the rich and fascinating cultural history as your weave through the historic centre, taking in splendid sights such as the Municipal Palace, Farnese Chapel, Podesta Palace and the Basilica of San Petronio.

The rest of today is yours to discover more of the city at your own pace. We recommend carving out some time to admire the treasures held in the archaeological museum.

The next stop on your great Italian adventure is the romantic city of Verona, which has been enshrined as the backdrop of Shakespeare’s Romeo and Juliet. Pull into the train station, meet your private driver and sit back and relax as you’re driven into the city centre. Your home for the next two nights here is an elegant hotel in the historic part of town.

After settling in and freshening up, head out and spend the afternoon taking the pulse of the city with a stroll through stylish streets lined with Veronese boutiques, romantic cafes and historic buildings.

Wake up bright and early to make the most of your one full day in the enchanting city of Verona. After a delicious breakfast at your hotel this morning, you’ll be met by a private guide to kick off today’s walking tour. Forever linked to the story of the star-crossed lovers, Verona is home to Juliet’s iconic home, whose balcony serves as a pilgrimage for many romantics. The city flourished at the time the play was written, and this can still be admired today through a succession of art and architectural treasures.

Spend the rest of the afternoon and evening further discovering the scenic and cultural delights of Verona at your own pace. We particularly recommend carving out time to visit the beautiful gardens hidden behind Giusti Palace. Established in the 15th century on the east bank of the Adige, the hillside garden has grown and blossomed over the centuries into an enchanting oasis of flowers, plants, century-old trees, statues, winding stairs and even a maze.

It’s time to bid Italy a warm farewell and embark on the six-hour train journey to Switzerland. Your final destination is colourful and cosmopolitan Zurich. This picturesque Swiss city is surrounded by incredible scenery, with the azure shores of Lake Zurich to one side and towering alpine mountains to the other. After settling in for the night in your charming centrally-located hotel, head out and make the most of your final day. We recommend heading into the heart of the cobblestone old town to wind your way through the elegant townhouses, luxury boutiques and renowned chocolatiers that call Zurich home.

Sadly, the time has come to begin the journey home. Enjoy one final stroll around town and a coffee in one of the many elegant, terraced cafes this morning before heading to the airport. After whizzing back through security, enjoy some downtime in the airport lounge with some nibbles and refreshments. Flight time back to the UK is just an hour and a half, so you’ll be back on home soil before you know it.

Alternatively, if you’d prefer to catch the train home, travel from Zurich to Paris this morning before catching a Eurostar back to London from there.

Suggestions

Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included

GOURMET STROLL THROUGH PALERMO'S MARKETS

To get a real sense of the way of life in Palermo, we’d suggest hitting the markets. People congregate here not only to shop, but to gossip and discuss local news while nibbling on snacks. Head into the heart of the market scene for a gourmet stroll with a local guide. Savour panelle, delicious Sicilian fritters, as you wander past pyramids of fluorescent spices and baskets of dried fruits. Round off your culinary adventure with a passeggiata (a walk after food) around the nearby churches and plazas.

MAZARA DEL VALLO LIKE A LOCAL

Tucked away in southwestern Sicily is Mazara del Vallo, a charming seaside town brimming with ancient history and culture. For centuries, the Casbah (the ancient fortified Arab citadel) and the Giudecca (the 15th-century Jewish quarter), have coexisted. Your guide for the day is a knowledgeable local, who will lead you through a labyrinth of picturesque streets filled with Byzantine charm. Round off your walk with a stop at a traditional dessert cafe to tuck into one of the region’s indulgent sweet treats.

Why visit Italy with Original Travel ?

Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.

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A few of the benefits of travelling with us to Italy

  • Our local Concierges
  • The Original Travel app
  • Airport lounge access
  • Destination Dossier
  • 24-hour helpline
  • Expert guides
  • 100% carbon absorption

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Estimated Price

Dependent on the season of travel, advance booking time and the accommodation and activities chosen

The prices shown here are merely a guide, as all of our trips are entirely tailor-made. Tailor-made travel involves multiple moving parts, and prices can vary hugely depending on the season of travel, the lead time before the proposed travel date (last minute deals are pretty much a myth), availability, your choice of accommodation and any additional activities you want to include. That means the only exact price will be the one we quote you, which we can adapt to suit your budget. The estimated starting cost for this trip is between £5,670 and £7,500 per person. The average starting price for this trip is £7,200 per person.

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