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
5
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8
9
10
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12
13
14
15
16
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18
19
20
21
22
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25
26
27
28
29
30
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2
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5
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10
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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 St. Peter's Basilica are good opportunities to explore the local culture. Your inner history buff will appreciate Pantheon and Roman Forum. There's lots more to do: explore the galleries of Vatican Museums, don't miss a visit to Trevi Fountain, contemplate in the serene atmosphere at Sistine Chapel, and take a stroll through Trastevere.

For traveler tips, photos, other places to visit, and more tourist information, you can read our Rome online road trip planner.

Toronto, Canada to Rome is an approximately 13-hour flight. Traveling from Toronto to Rome, you'll lose 6 hours due to the time zone difference. While traveling from Toronto, expect somewhat warmer days and about the same nights in Rome, ranging from highs of 81°F to lows of 60°F. Wrap up your sightseeing on the 14th (Tue) early enough to 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 The Neapolis Buried. You'll get in some beach time at Fornillo and Marina di Puolo. Explore the numerous day-trip ideas around Naples: Villa di Pollio Felice - Bagni della Regina Giovanna (in Sorrento), Salerno (Bossa & Duomo di Salerno) and Le Vigne di Raito (in Raito). The adventure continues: delve into the distant past at Pompeii Archaeological Park, contemplate the long history of Teatro Greco-Romano, examine the collection at Certosa e Museo di San Martino Napoli, and make a trip to Spaccanapoli.

To see maps, traveler tips, ratings, and other tourist information, read our Naples trip itinerary maker app.

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. On the 19th (Sun), wrap the sightseeing up by early afternoon so you can drive to Assisi.

Things to do in Naples

Historic Sites · Museums · Outdoors · 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 Assisi Galleria 6C. Get some cultural insight at Basilica Papale e Sacro Convento di San Francesco d'Assisi and Eremo delle Carceri. There's still lots to do: step into the grandiose world of Rocca Maggiore, take in the spiritual surroundings of Basilica di Santa Chiara, take in the architecture and atmosphere at San Damiano, and stop by Il Tapiro.

To see maps, ratings, other places to visit, and other tourist information, refer to the Assisi road trip website.

Drive from Naples to Assisi in 4 hours. Alternatively, you can take a train; or take a bus. Traveling from Naples in September, Assisi is slightly colder at night with lows of 57°F. Cap off your sightseeing on the 23rd (Thu) early enough to 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 The Baptistery of St. John for their historical value. Give yourself a bit of retail therapy at Mercato Centrale and Paolo Penko. 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 · Outdoors · Nightlife · 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 Museo di Castelvecchio. Do your shopping at Piazza delle Erbe and Fondazione Bisazza. 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, take in the architecture and atmosphere at Basilica Santa Teresa di Gesu Bambino, admire the striking features of Casa di Giulietta, and explore the historical opulence of Piazzale Castel San Pietro.

To see maps, photos, traveler tips, and more tourist information, read Verona trip planner.

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

Things to do in Verona

Historic Sites · Wineries · Shopping · Museums

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 Basilica di San Marco 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, explore the world behind art at Peggy Guggenheim Collection, 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 · Shopping

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.