The Ultimate First-Time-To-Italy Train Itinerary


Italy holds a special place in many travelers’ hearts and bucket lists, yet it means something different to everyone: ancient cities, mesmerizing coasts, unbelievable architecture, rare frescoes, delicious wine, rich food, and a certain swagger up and down the famous peninsula. So how do you choose where to go?

Good news: you don’t necessarily need to. You can see all of Italy with the Italy rail pass – from mountainous, cosmopolitan Milan in the north to romantic Venice, renaissance Florence, and historic Rome.  Here are our tips for the perfect Italian bucket list vacation.


Up in the mountains of the Lombardy region of northern Italy, Milan is Italy’s most cosmopolitan city. Milan is absolutely brimming with high fashion, fine dining, and chic citizens personifying true Italian elegance. Places like the Casa Museo Bochi home art gallery and Pinacoteca Ambrosiana library walk the fine line between modern and historic that Milan balances so well. A walk through Corso Magenta will sate anyone’s desire for fashion boutiques and savory cafes. Ancient and Renaissaince-era sights are abundant, too, including Sforza Castle, the Milan Duomo, and, of course, a glimpse at Da Vinci’s masterpiece The Last Supper in the Basilica di Santa Maria. 


Venice is simply a daydream. Famously built on a lagoon and boasting 177 (!) canals,  a gondola ride is all you need to appreciate the romanticism of a trip to Venice. The city’s beauty extends far beyond the canals to the ornate Basilica di San Marco and magnificent Palazzo Ducale. Venice is also imminently walkable, so crisscrossing the old city on quaint footpaths and ancient bridges is an absolute pleasure. And if you’re traveling in February, it doesn’t get much more exciting than the incredible Venice Carnival street festival celebrating Lent with masks and plenty of partying. 

Milan to Venice by train: 2h 25min, via Frecciarossa or Italo trains


Just a quick train ride from Venice, the islands of Murano are a perfect day trip for travelers seeking quiet waterfront life along the Venetian lagoon. Murano is famous for its long history of glassblowing, beautifully on display at the Museo del Vetro glass museum. Incredible glassworks are found across the island, too, from the Campo San Stefano to the Chiesa di San Pietro Martire church. 


Florence was once Italy’s wealthiest city, springing the Renaissance – and modern European art and culture – to life. Thankfully, many of these amazing relics and works are still open to the public today. The Uffizi Gallery is the largest collection of Renaissance art anywhere in the world, while the Basilica di Santa Maria Novella contains immaculate frescoes by legendary artists. You can top it all off by seeing Michelangelo’s brilliant sculpture David in Galleria dell’Accademia. To experience Florence’s active cafe scene, head to Piazza della Repubblica for espresso and people-watching. 

Venice to Florence by train1h 53min, Frecciargento or Italo 


Lean into Pisa for a fun day trip to the famous eponymous Torre di Pisa and much more. Other architectural wonders (that actually stand up straight!) are just as magnificent: Piazza dei Miracoli is one of Europe’s most beautiful public squares and the Battistero is pretty grand too. For a dose of the unconventional, Palazzo Blu has to be just about the coolest modern art museum in Tuscany, with outright groundbreaking exhibitions rotating year-round. 

Florence to Pisa by train1h via Intercity (non-high speed) trains

San Gimignano and Siena

For a unique trek through Tuscany, the walled city of San Gimignano is unlike anything you’ve seen before. The fourteen medieval ramparts that guard the spectacular town date back to 1199, but San Gimignano can trace its roots back to an Etruscan village (yeah, those were the folks around before the Romans). More treasures await inside the walls, including the Collegiate cathedral and Palazzo Comunale – where a quick hike up the spire reveals a breathtaking view. Nearby Siena offers even more medieval inspiration, where the entire city center is a UNESCO World Heritage Site thanks to incredible architectural wonders like Siena CathedralPiazzo del Campo, and Palazzo Salimbeni.  How to get there by train?

Florence to Siena by train: 1.5 hours
Siena to San Gimignano by train: about 25 minutes


Rome was founded by seven kings and has seven hills, but there are about seven million reasons to visit The Eternal City. Rome shaped Europe more than anywhere else and the city is so full of wonders it’s impossible to run out of adventures. Mandatory stops include the ancient Parthenon temple, St. Peter’s BasilicaColosseumForum, Villa Borghesi, and Vatican holy sites. To feast on the chill vibe of modern Rome, all it takes is a hang at the Piazza del Popolo or a trek up Gianicolo Hill. 

Florence to Rome by train: 1.5 hours


Naples is Italy’s raw, authentic heart and soul. Bustling streets lined with amazing food vendors (yes, Naples has the best pizza in Italy!) and famous street art welcome travelers on their way to Castel dell’Ovo, iconic Duomo, and impressive Museo Archeologico Nazionale. Day trips from Naples are a fantastic way to see the incredible coastline too. For a truly surreal experience, trapse the underground Galleria Borbonica bourbon tunnels. 

Rome to Naples by train: Time varies depending on stations + train company


Infamous for the deadly volcanic eruption of Mount Vesuvius that buried the ancient city and most of its inhabitants in 79 AC, the ruins of the original Pompei are still being uncovered. Visiting the town today is truly an archaeological journey unto itself. The Forumbaths, and theater are all still intact and absolutely worth the short train ride from Naples. Many visitors choose to climb the slopes of the now-quiet Vesuvius and catch an incredible view of the Campania countryside. 

So what do you think? Ready to head off to Italy by train?

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