Itinerary Highlights
    • Embrace slow travel as you wind through Italy on scenic train journeys.
    • Relax with overnight stops in Milan and Naples.
    • Explore Sicily’s Taormina and Syracuse on privately guided tours.

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Live la dolce vita on this nine-day train trip to the sweet and sun-baked Sicily. Nestled at the tip of Italy’s boot, this little island has its own charming personality, from Mount Etna's peak to the sparkling seas. Home to some of Europe’s finest ancient Greek ruins, there’s plenty to entertain history buffs and sun seekers alike.

The train journey to Sicily will first take you through Milan, Europe’s glitzy fashion capital. Next, spend a night in Naples, the birthplace of everyone’s favourite Italian dish – pizza. Hop on the next train and head onwards to Sicily, where you’ll spend the next six nights in Taormina and Syracuse, quaint coastal destinations that perfectly capture Sicily’s charm.

This itinerary can either be done entirely by train or can be turned into an ‘Aerotrain’ itinerary, where one way is a quick hop by aeroplane and the other way is a leisurely train ride.


Everything is 100% tailored to you

London to Milan

Wake up with the birds and get ready to board your early morning Eurostar train from London to Paris. After arriving at around nine, hop off the first train and onto the second, this time bound for Milan. Soak in the scenery from your window as you roll through France and into Italy, arriving in Milan just in time for dinner. Dump your bags at your hotel, change into your best outfit and head out into the fashion capital for an evening of pizza munching and Aperol sipping.


Onwards to Naples

Head out bright and early in time for your nine o'clock train to Naples. Enjoy the rolling countryside from the comfort of your seat as you chug down the leg of Italy’s boot, arriving in Naples at around two in the afternoon. Check into your hotel nestled in the city’s historic district and venture out to explore some of Naple’s hotspots: the Archaeological Museum, which houses artefacts from the Greek and Roman times; the old town, dubbed a UNESCO World Heritage site; and Piazza Bellini, where bars bubble over with thirsty visitors. When your bellies start to rumble, ask your local Concierge to book you into one of the many bustling restaurants serving pizza with fluffy, charred dough and pasta dripping with rich tomato sauce.


Train ride to Taormina

It’s another day, and there’s another gorgeous train ride ahead of you. Today also marks your arrival in Sicily, so make your way to Naple’s train station and begin your journey to Taormina, a hilltop town on the east coast of the island. Your late-afternoon arrival gives you plenty of time to get your bearings of this quaint coastal town after checking into your hotel (and admiring the panoramic views of Mount Etna and the Ionian Sea).

DAYS 4 & 5


Start your first morning in Taormina with a Sicilian special – a refreshing glass of granita, a semi-frozen drink made from juice or water, sugar and fresh fruit or flavouring. Typically paired with brioche col tuppo (an Italian take on a brioche roll stuffed with gelato), it’s the perfect fuel for your private tour of Taormina. Over the next two hours, explore the town alongside an English-speaking guide and discover the ancient ruins, lively terraces, clifftop views and cobbled streets at your own pace. As your day draws to a close, settle into one of the four Michelin-starred restaurants showcasing Sicilian dishes centred around freshly caught seafood.

During your next day in Taormina, revisit your favourite spots from yesterday or venture to places you missed. For example, the Teatro Antico di Taormina is an unmissable Greco-Roman ancient amphitheatre built in the third century, carved into the cliff between the sea and sky. Snap some stunning pictures of Mount Etna and Italy’s Calabrian coast alongside your cheesy grins before seeking out one final Taormina dinner.


Head down the coast to Syracuse

Today, you’re heading down Sicily’s east coast towards Syracuse, a city that sums up why this island is a world-famous destination. The train journey is just a couple of hours, giving you enough time to marvel at the Sicilian views while having plenty of the day left to play with. Check into your harbour-side hotel before heading out to explore the gorgeous shorelines, historical wonders, open-air bars and eateries offering delectable dishes.

DAYS 7 & 8


Syracuse was founded in 734 BC, and today you’ll peel back the historical layers alongside a private guide. Step back in time and discover the sites within the Neapolis Archaeological Park: the Teatro Greco, an ancient Roman amphitheatre that’s still in use today, and the Orecchio di Dionisio, a limestone cave shaped like a human ear.

The city has a lot to offer outside of the Archaeological Park. Make sure to check out Ortigia, a small Baroque Island and UNESCO World Heritage site that’s dotted with impressive church facades, elegant restaurants and pretty piazzas. Come evening, grab a seat overlooking the Ionian Sea and enjoy a farewell drink as the sun sets on your last evening in Sicily.


Fly to London

It’s the final morning of your holiday, so grab one last glass of granita before being privately transferred to Catania airport. The flight is a speedy three-and-half hours, offering sky-high views and plenty of time to reminisce over your sweet Sicilian adventure.

A Rough Idea of Price

Dependent on season, accommodation and activities
The cost for this trip starts from £1,800 to £2,900 per person.

The final cost of the trip depends on the way we tailor it especially for you. The final cost varies according to several factors, which include the level of service, length of trip and advance booking time. The exact price will be provided on your personalised quote.

The average starting price for this trip is £2,300 per person.
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