33 days in Italy Itinerary

33 days in Italy Itinerary

Created using Inspirock Italy planner

Make it your trip
Fly
1
Rome
— 6 nights
Train
2
Naples
— 5 nights
Drive
3
Assisi
— 4 nights
Drive
4
Florence
— 6 nights
Train
5
Milan
— 2 nights
Drive
6
Verona
— 4 nights
Drive
7
Venice
— 5 nights
Fly

S M T W T F S
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12
13
14
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30
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Rome

— 6 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Colosseum and Pantheon are good opportunities to explore the local culture. Your inner history buff will appreciate Vatican Museums and Piazza Navona. The adventure continues: don't miss a visit to St. Peter's Basilica, explore the world behind art at Galleria Borghese, explore the ancient world of Palatine Hill, and get engrossed in the history at Musei Capitolini.

To see more things to do, where to stay, other places to visit, and other tourist information, you can read our Rome vacation website.

Toronto, Canada to Rome is an approximately 13-hour flight. You'll lose 6 hours traveling from Toronto to Rome due to the time zone difference. Expect a bit warmer weather when traveling from Toronto in September: highs in Rome hover around 81°F, while lows dip to 60°F. Finish your sightseeing early on the 14th (Tue) so you can take a train to Naples.

Things to do in Rome

Historic Sites · Museums · Neighborhoods · Parks

Side Trip

Find places to stay Sep 8 — 14:

Naples

— 5 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You'll explore and learn at Museo Cappella Sansevero and Museo e Real Bosco di Capodimonte. You'll get in some beach time at Fornillo and Marina di Puolo. Explore the numerous day-trip ideas around Naples: Le Vigne di Raito (in Raito), Salerno (Bossa & Duomo di Salerno) and Villa di Pollio Felice - Bagni della Regina Giovanna (in Sorrento). There's much more to do: explore the ancient world of Pompeii Archaeological Park, take in the architecture and atmosphere at Basilica di San Pietro ad Aram, go for a walk through Lungomare Caracciolo, and see the interesting displays at Certosa e Museo di San Martino Napoli.

For reviews, traveler tips, photos, and more tourist information, read our Naples day trip planning site.

Take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. September in Naples sees daily highs of 80°F and lows of 64°F at night. Wrap up your sightseeing by early afternoon on the 19th (Sun) to allow time for the car ride to Assisi.

Things to do in Naples

Historic Sites · Museums · Beaches · Parks

Side Trips

Find places to stay Sep 14 — 19:

Assisi

— 4 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Give yourself a bit of retail therapy at B.A.T. Assisi and Il Tapiro. Get some cultural insight at Basilica Papale e Sacro Convento di San Francesco d'Assisi and Oratorio dei Pellegrini. The adventure continues: take in the spiritual surroundings of Eremo delle Carceri, take in the exciting artwork at Assisi Galleria 6C, step into the grandiose world of Rocca Maggiore, and look for gifts at La mela in tasca.

For reviews, maps, and more tourist information, go to the Assisi trip planner.

You can drive from Naples to Assisi in 4 hours. Other options are to take a train; or take a bus. Traveling from Naples in September, plan for a bit cooler nights in Assisi, with lows around 57°F. Finish up your sightseeing early on the 23rd (Thu) so you can go by car to Florence.

Things to do in Assisi

Shopping · Historic Sites · Museums · Parks
Find places to stay Sep 19 — 23:

Florence

— 6 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Visit Cathedral of Santa Maria del Fiore and Piazza del Duomo for their historical value. Give yourself a bit of retail therapy at Mercato Centrale and Spezierie Palazzo Vecchio Dott.Di Massimo. Venture out of the city with trips to Siena (Take Me Out in Tuscany & Duomo di Siena). There's much more to do: explore the world behind art at Gallerie Degli Uffizi, appreciate the extensive heritage of Piazza della Signoria, don't miss a visit to Piazzale Michelangelo, and contemplate the long history of Basilica of Santa Croce.

For where to stay, photos, more things to do, and tourist information, use the Florence trip planner.

You can drive from Assisi to Florence in 2.5 hours. Another option is to take a train. September in Florence sees daily highs of 78°F and lows of 59°F at night. Finish your sightseeing early on the 29th (Wed) so you can take a train to Milan.

Things to do in Florence

Historic Sites · Museums · Tours · Shopping

Side Trip

Find places to stay Sep 23 — 29:

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.
Give yourself a bit of retail therapy at Galleria Vittorio Emanuele II and Azalea - Silk of Como. Visit Duomo di Milano and Castello Sforzesco for their historical value. Explore Milan's surroundings by going to Al Puunt-Snack Beach Bar (in Griante) and Lido di Faggeto Miamilaryo (in Faggeto Lario). There's more to do: take an in-depth tour of Pinacoteca Ambrosiana.

To find photos, more things to do, maps, and more tourist information, read our Milan attractions website.

You can take a train from Florence to Milan in 2.5 hours. Alternatively, you can drive; or take a bus. In September, daytime highs in Milan are 76°F, while nighttime lows are 57°F. Wrap up your sightseeing on the 1st (Fri) to allow time to drive to Verona.

Things to do in Milan

Historic Sites · Nightlife · Outdoors · Museums

Side Trips

Find places to stay Sep 29 — Oct 1:

Verona

— 4 nights

City of Romeo and Juliet

The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Get a sense of the local culture at Arena di Verona and Fondazione Bisazza. Do your shopping at Piazza delle Erbe and Piacere Divino Enoteca E Vini Sfusi. Go for a jaunt from Verona to Calmasino to see Villa Calicantus about 34 minutes away. There's lots more to do: contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, explore the ancient world of Operaforte, explore the historical opulence of Museo di Castelvecchio, and admire the landmark architecture of Casa di Giulietta.

To find more things to do, maps, and other tourist information, go to the Verona driving holiday planning app.

You can drive from Milan to Verona in 2 hours. Alternatively, you can take a train. In October in Verona, expect temperatures between 66°F during the day and 50°F at night. Finish your sightseeing early on the 5th (Tue) to allow enough time to drive to Venice.

Things to do in Verona

Historic Sites · Wineries · Shopping · Neighborhoods

Side Trips

Find places to stay Oct 1 — 5:

Venice

— 5 nights

City of Romance

Virtually unchanged for the last six centuries, Venice is actually a group of islands made famous by a series of canals, bridges, monuments, piazzas, and narrow pedestrian lanes.
Shop till you drop at I Tre Mercanti and Mater Domini. Piazza San Marco and Peggy Guggenheim Collection are good opportunities to explore the local culture. You'll find plenty of places to visit near Venice: Padua (Caffe Pedrocchi, Basilica of St. Anthony, &more). The adventure continues: admire the striking features of Doge's Palace, take in panoramic vistas at St Mark's Campanile, take in the architecture and atmosphere at Basilica di San Marco, and contemplate the waterfront views at Canal Grande.

To find ratings, traveler tips, maps, and more tourist information, use the Venice trip planner.

Drive from Verona to Venice in 1.5 hours. Alternatively, you can take a shuttle; or take a train. In October, daytime highs in Venice are 66°F, while nighttime lows are 51°F. Cap off your sightseeing on the 10th (Sun) early enough to catch the flight back home.

Things to do in Venice

Historic Sites · Museums · Neighborhoods · Nightlife

Side Trip

Find places to stay Oct 5 — 10:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.