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
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
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14
15
16

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 St. Peter's Basilica. The adventure continues: don't miss a visit to Piazza Navona, 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.
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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 Archeologico Nazionale di Napoli. 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). There's lots more to do: delve into the distant past at Pompeii Archaeological Park, explore the galleries of The Neapolis Buried, take in the architecture and atmosphere at Cloister of Santa Chiara, and explore the world behind art at Museo e Real Bosco di Capodimonte.

To find traveler tips, photos, where to stay, and tourist information, refer to the Naples trip planning website.

Getting from Rome to Naples by train takes about 2 hours. Other options: drive; or fly. In September in Naples, expect temperatures between 80°F during the day and 64°F at night. Wrap up your sightseeing by early afternoon on the 19th (Sun) to allow time for the car ride to Assisi.
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Historic Sites · Museums · Parks · Beaches
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. There's still lots to do: contemplate in the serene atmosphere at Eremo delle Carceri, pause for some serene contemplation at Chiesa Santo Stefano, step into the grandiose world of Rocca Maggiore, and stop by Terra Umbra.

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.
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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 Campanile di Giotto 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). And it doesn't end there: admire the masterpieces at Gallerie Degli Uffizi, indulge in some culinary diversions at a local gastronomic tour, pause for some serene contemplation at Basilica of Santa Croce, and don't miss a visit to Piazzale Michelangelo.

To see maps, reviews, photos, and other tourist information, read Florence itinerary site.

Traveling by car from Assisi to Florence takes 2.5 hours. Alternatively, you can take a train. In September in Florence, expect temperatures between 78°F during the day and 59°F at night. Cap off your sightseeing on the 29th (Wed) early enough to catch the train to Milan.
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Museums · Historic Sites · 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 Lido di Faggeto Miamilaryo (in Faggeto Lario) and Al Puunt-Snack Beach Bar (in Griante). There's more to do: admire the masterpieces at 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.
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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 Piazza delle Erbe and Museo di Castelvecchio. Do your shopping at Via Mazzini and Piacere Divino Enoteca E Vini Sfusi. Change things up with these side-trips from Verona: Villa Calicantus (in Calmasino) and Fondazione Bisazza (in Montecchio Maggiore). There's lots more to do: see a show at Arena di Verona, explore the ancient world of Operaforte, take in the spiritual surroundings of Basilica di San Zeno Maggiore, and examine the collection at 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.
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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 Magie di Carnevale. 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 Basilica di San Marco, take in the views from Ponte dei Sospiri, examine the collection at Doge's Palace, 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.
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Historic Sites · Museums · Neighborhoods · Shopping
Side Trip
Find places to stay Oct 5 — 10:

Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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