11 days in Northwest Italy Itinerary
Created using Inspirock Italy trip itinerary builder
Start: Philadelphia
Fly
1
Rome
— 2 nights
Train
2
Florence
— 2 nights
Drive
3
Siena
— 3 nights
Drive
4
Florence
Train
5
Milan
— 2 nights
Fly to New York JFK, Train to Philadelphia
End: Philadelphia
Wed, Sep 14 - Sat, Sep 24
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Rome — 2 nights
Eternal City
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.Kick off your visit on the 15th (Thu): explore the ancient world of Abbazia delle Tre Fontane, then wander the streets of Ghetto Ebraico, and then contemplate the long history of Arco di Tito. Keep things going the next day: explore the world behind art at Villa Farnesina, then pause for some serene contemplation at Basilica Parrochiale San Lorenzo in Lucina, then take in the architecture and atmosphere at Basilica dei SS. Ambrogio e Carlo al Corso, and finally take in the architecture and atmosphere at Chiesa di Sant'Andrea al Quirinale.
For ratings, more things to do, where to stay, and tourist information, you can read our Rome online attractions planner.
Philadelphia, USA to Rome is an approximately 13.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. In September, daytime highs in Rome are 81°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 17th (Sat) early enough to take a train to Florence.
Highlights from your trip
Florence — 2 nights
Birthplace of the Italian Renaissance
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.Kick off your visit on the 17th (Sat): admire the landmark architecture of Chiesa di San Salvatore in Ognissanti, browse the exhibits of Basilica di San Lorenzo, then take in the exciting artwork at M.G. Design, then examine the collection at Mus.e Firenze Palazzo Vecchio, and finally ponder the design of Fountain of Neptune. Keep things going the next day: enjoy breathtaking views from Torre di Arnolfo, get engrossed in the history at Corridoio Vasariano, then wander the streets of Oltrarno, then explore the venue of Palazzo Strozzi, and finally take in the architecture and atmosphere at Holy Trinity.
To find photos, traveler tips, reviews, and tourist information, you can read our Florence travel route planner.
Traveling by train from Rome to Florence takes 2.5 hours. Alternatively, you can fly; or drive. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Wrap up your sightseeing on the 19th (Mon) early enough to drive to Siena.
Highlights from your trip
Siena — 3 nights

Cultural Heart of Tuscany
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.Cappella di Piazza and Basilica di San Clemente in Santa Maria dei Servi will appeal to history buffs. Appreciate the collections at Dievole and Ceramiche Bianco e Nero di Staccioli. You'll find plenty of places to visit near Siena: Cortona (Piazza Garibaldi, Chiesa San Francesco, &more) and Icario Winery (in Montepulciano). There's lots more to do: admire the masterpieces at Parco Sculture Del Chianti, learn about all things military at Fortezza Medicea, appreciate the extensive heritage of Piazza Salimbeni, and get outside with Siena Bike Shop.
For photos, maps, more things to do, and tourist information, go to the Siena travel planner.
You can drive from Florence to Siena in 1.5 hours. Other options are to take a bus; or take a train. In September, daytime highs in Siena are 81°F, while nighttime lows are 61°F. Finish your sightseeing early on the 22nd (Thu) to allow enough time to drive to Florence.
Side Trips
Highlights from your trip

Birthplace of the Italian Renaissance
For other places to visit, reviews, and tourist information, refer to the Florence tour planner.
You can drive from Siena to Florence in 1.5 hours. Other options are to take a bus; or take a train. On the 22nd (Thu), you'll travel to Milan.
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You can drive from Siena to Florence in 1.5 hours. Other options are to take a bus; or take a train. On the 22nd (Thu), you'll travel to Milan.
Milan — 2 nights
Fashion Capital of World
In many ways the most modern of Italian cities, Milan is a busy, elegant metropolis with an impressive list of grand palaces, fine churches, and important museums.Kick off your visit on the 23rd (Fri): explore the world behind art at Museum of Ancient Art, explore the world behind art at Museum of Decorative Arts, explore the world behind art at Museo Pieta Rondanini, then identify plant and animal life at Wildlife Areas, and finally examine the collection at The Bramante Sacristy.
To find where to stay, other places to visit, maps, and other tourist information, read our Milan online travel route planner.
Traveling by train from Florence to Milan takes 2.5 hours. Alternatively, you can drive; or take a bus. In September in Milan, expect temperatures between 76°F during the day and 57°F at night. Finish your sightseeing early on the 24th (Sat) to allow enough time to travel back home.
Highlights from your trip