Italy by Train Itinerary

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Advisor - Francesca Iannaccone
Curated By

Francesca Iannaccone

  • Italy

  • Food & Wine

  • Active Travel

  • Arts & Culture

  • Outdoors

  • Entertainment

  • Local Food

Stairs and a fountain in front of a building.
Curator’s statement

Italy holds a deeply personal significance for me, being Italian by heritage. Growing up, I learned to cook Italian food from the recipes passed down through generations. The country's rich history, art and cuisine are not just elements of travel but threads woven into my own identity. Having visited Italy numerous times, and having stayed in various regions, this Italy by Train itinerary reflects the love and connection I have with this extraordinary country. From the romantic canals of Venice to the ancient ruins of Rome, each stop is infused with memories and a deep appreciation for the Italian way of life. Please note the itinerary below is listed for just 5 days. This itinerary should be spread out across as many visiting days as possible to avoid too many transfers in too few days, resulting in a travel burn out! We want your vacation to be exciting, enjoyable, luxurious and relaxing!

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Day 1: Venice - The City of Canals

train through mountain region

Begin your Italian adventure in the magical city of Venice. Explore the historic St. Mark's Square, take a gondola ride through narrow canals, and visit the Doge's Palace. Don't miss the chance to savor authentic Venetian cuisine in a local trattoria.

Insider Tip: Rise early to experience the tranquil beauty of Venice before the crowds arrive. I personally find Venice very small in size, and have comfortably spent just 1-2 days before feeling ready to move on!

Day 2: Florence - Renaissance Splendor

City river with buildings on side.

Board the high-speed Frecciarossa train from Venice's Santa Lucia Station to Florence. Explore the historic heart of Florence, visiting the Uffizi Gallery to witness masterpieces by Michelangelo and Botticelli. Climb the iconic Duomo for panoramic views of the city and indulge in a Tuscan feast at a traditional osteria.

Insider Tip: Reserve tickets to the Uffizi Gallery in advance to skip the lines. If you are feeling even more adventurous, reserve tickets to climb to the very very top of the famous Duomo. Ancient passageways carved into the building spiral up to an incredible view of the city unlike any other. Not for the faint of heart or those with fear of tight spaces or heights!

Day 3: Siena - Medieval Majesty

Aerial view of city buildings during day time.

Take a scenic regional train to Siena, a city frozen in medieval times. Explore the magnificent Piazza del Campo, visit the stunning Siena Cathedral, and wander through the narrow streets lined with charming shops and cafes.

Insider Tip: Climb the Torre del Mangia for breathtaking views of the city and surrounding countryside.

Day 4: Rome - The Eternal City

An iron pan filed with pasta

Travel to Rome on the Frecciarossa. Explore the Colosseum, Roman Forum, and Pantheon. Stroll through charming neighborhoods like Trastevere, and indulge in classic Roman dishes at a local osteria.

Insider Tip: Stay at The Hoxton for a stylish and contemporary Roman experience.

Day 5: Verona - Romantic Elegance

Table in outdoor alleyway

Take a Frecciargento train to Verona, the city of Romeo and Juliet. Explore the well-preserved Roman Arena, stroll through the romantic streets, and visit Juliet's House. Enjoy a leisurely day in one of Italy's most charming cities.

Insider Tip: Stay at Vista Palazzo for a luxurious and romantic stay in Verona.

Advisor - Francesca Iannaccone

Travel Advisor

Francesca Iannaccone

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For more Italy travel inspiration by Ann, check out her guide, Foodie's Guide to Piedmont.

This guide is part of our ongoing series on travel to Italy.