South to Sicily

South to Sicily

from £3,066 excluding flights

  • 15 nights
  • Year round
  • Multi-destination
  • Rail
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South to Sicily

from £3,066 excluding flights

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

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Highlights

In pictures
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Discover authentic Italian cuisine in Naples

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Enjoy private tours of Herculaneum and Pompeii

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Explore three volcanoes: Vesuvius, Etna and Stromboli

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Visit Agrigento’s Valley of the Temples with a private guide

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Explore Ortygia, the magnificent ancient centre of Syracuse

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Take in the incredible views from Taormina’s ancient theatre

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

From London to the tip of Italy, this captivating rail journey to Sicily is all about slow travel, immersing yourself in ever-changing scenery as you travel south through Europe. First to Paris, then Milan and on through Tuscany to Naples, simply sit back and enjoy a kaleidoscope of towns, cities, mountains and lakes. You won’t reach Sicily until day 5, giving you plenty of time en route to explore Milan and Naples. One day you could be gazing at da Vinci’s The Last Supper, the next you might be scaling the slopes of Mt Vesuvius or roaming the ruins of Herculaneum and Pompeii with your private guide.

Crossing the Straits of Messina to Sicily, an in-depth exploration of this fascinating island awaits, travelling by train between the historic gems of Taormina, Syracuse, Palermo and Cefalú, visiting the World Heritage Site of Agrigento and the brooding volcanoes of Etna and Stromboli. Then you have a choice: either fly back to the UK, or take the sleeper train to Rome where you can extend your holiday before returning home via Zürich and Paris.

Bay of Naples

Lying in the shadow of Vesuvius, Naples is the jumping-off point for excursions to the haunting, mesmerising ruins of Herculaneum and Pompeii – both of which you’ll visit in the company of a private guide. Such was the ferocity of Vesuvius’ eruption on 24th August AD79, it petrified both towns in ash, mud and lava. Excavated ruins have revealed everything from cart tracks and carbonised bread to temple remains and – most poignant of all – the human figures of victims cowering under the volcanic onslaught. Both sobering and spellbinding, few places offer a more vivid glimpse into life in Roman times nearly 2,000 years ago. By contrast, Naples offers a wonderfully chaotic mix of contemporary Italian street life and historic buildings. Spaccanapoli, a narrow, canyon-like street, threads between churches and statues; its cobbles crowded with street vendors and its shops selling everything from pasta to Neapolitan masks. Cafés overflow with locals sipping coffee, while open-air restaurants serve delicious pizza Margherita – the most authentic in Italy.

Sicily

Only 3km from the toe of Italy, Sicily’s vineyards, olive groves and citrus plantations glisten beneath the smoking hulk of Europe’s largest volcano – 3,370m Mt Etna. Regularly bubbling over with spectacular pyrotechnics, this is also the world’s second most active volcano and you’ll gain a riveting insight into the grumbling giant on a guided tour. On another day during your rail journey around Sicily, you can take an optional boat trip to the Aeolian Islands to witness a second volcano – Stromboli – that has been active for more than two millennia. But there is so much more to Sicily than fire and brimstone. The local cuisine, for example, is an irresistible fusion of Italian, Arabic, French and Spanish, so expect dishes rich in olive oil, dried fruit, Mediterranean herbs and spices, locally-caught fish and traditional breads, cheeses and wines. Sicily’s historical sights are equally palatable. Your itinerary is full of ancient wonders, from the UNESCO World Heritage-listed Valley of the Temples at Agrigento to the medieval fishing town of Cefalú.

Milan, Zurich, Rome…

As if the Bay of Naples and Sicily weren’t enough, rail travel allows this itinerary to be book-ended with overnight stays in some of Europe’s cultural superstars: Milan, Zurich and Rome (the Italian capital being an optional extension). Trendy Milan blends designer labels and fashion boutiques with artistic masterpieces ranging from The Last Supper to the Duomo di Milano cathedral, while Zurich is Switzerland at its most savvy, with a medieval Old Town adorned with magnificent guildhalls and elegant squares. Extend your holiday in Rome and you can add the Colosseum, Roman Forum, Pantheon and Vatican as the ultimate finishing touches to your rail odyssey.

Itinerary

Day 1 London - Milan

Depart London in the morning and travel by Eurostar to Paris Gare du Nord. Transfer to Gare de Lyon, just two stops on the Paris PER, in time for lunch before departing on your onward 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 de Lyon, just two stops on the Paris PER, in time for lunch before departing on your onward journey to Milan. Following two nights in Milan.

Day 2 Milan

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.

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.

Day 3 Milan - Naples

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.

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.

Day 4 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.

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.

Day 5 Naples - Taormina

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.

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.

Days 6-8 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 three nights in 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 three nights in Taormina.

Day 9 Taormina - Syracuse

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.

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.

Day 10 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.

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.

Day 11 Syracuse to Agrigento

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. Afterwards, round off a memorable day with a private tour of the nearby Turkish Steps – a dazzling stretch of white, layered cliffs sloping into the turquoise sea. There can be few better places to enjoy a Mediterranean sunset. Overnight in Agrigento.

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. Afterwards, round off a memorable day with a private tour of the nearby Turkish Steps – a dazzling stretch of white, layered cliffs sloping into the turquoise sea. There can be few better places to enjoy a Mediterranean sunset. Overnight in Agrigento.

Day 12 Syracuse - Palermo

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. Overnight Palermo.

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. Overnight Palermo.

Day 13 Palermo - Cefalú

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.

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.

Day 14 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.

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.

Day 15 Zurich

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.

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.

Day 16 Zurich - London, via Paris

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.

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.

Extend Your Stay

If you’d like to spend a few extra days in Rome, we can easily fit this into your holiday.

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Rome

Explore all the classic sights of the Italian capital – from the Colosseum and Roman Forum to the Pantheon and Trevi Fountain. 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.

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.

Prices and Departures

Price from £3,066 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 travel
  • All compulsory seat reservation fees on high-speed and international trains
  • Private tour of Herculaneum and Pompeii
  • Private 4x4 tour to Mt Etna
  • Transfer to Agrigento and private tour to the Valley of the Temples
  • Private sunset tour to the Turkish Steps
  • 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 Rail / Flight
Year Round 15 nights £3066 Round trip by rail
Year Round 14 nights £2356 Fly back on Day 15 - 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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