31 days in Italy Itinerary

31 days in Italy Itinerary

Created using Inspirock Italy holiday planner

Make it your trip
Fly
1
Venice
— 4 nights
Fly
2
Amalfi
— 4 nights
Drive
3
Naples
— 3 nights
Train
4
Rome
— 5 nights
Drive
5
Assisi
— 3 nights
Drive
6
Siena
— 3 nights
Drive
7
Florence
— 4 nights
Train
8
Verona
— 2 nights
Drive
9
Milan
— 2 nights
Fly

S M T W T F S
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26
27
28
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30
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31
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Venice

— 4 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.
When in Venice, make a side trip to see Basilica of St. Anthony in Padua, approximately Padua away. And it doesn't end there: explore the activities along Canal Grande, admire the masterpieces at Peggy Guggenheim Collection, take in the views from Ponte dei Sospiri, and let your taste buds guide you at a local gastronomic tour.

To find more things to do, other places to visit, traveler tips, and more tourist information, read our Venice road trip planning tool.

Toronto, Canada to Venice is an approximately 11.5-hour flight. You'll lose 6 hours traveling from Toronto to Venice due to the time zone difference. When traveling from Toronto in October, plan for a bit warmer days and about the same nights in Venice: temperatures range from 22°C by day to 12°C at night. Finish your sightseeing early on the 5th (Wed) so you can fly to Amalfi.

Things to do in Venice

Side Trip

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Amalfi

— 4 nights

Painted Town

Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.
Explore the numerous day-trip ideas around Amalfi: Positano (Fornillo, Il Sentiero Degli Dei, &more). There's still lots to do: indulge your senses at Amalfi Coast Drive, see the interesting displays at Museo della Carta, appreciate the extensive heritage of Centro Storico, and take a memorable drive along Amalfi Coast.

To see photos, where to stay, reviews, and more tourist information, refer to the Amalfi tour planning app.

Getting from Venice to Amalfi by flight takes about 3 hours. Other options: do a combination of train and taxi; or drive. In October, Amalfi is somewhat warmer than Venice - with highs of 26°C and lows of 20°C. Cap off your sightseeing on the 9th (Sun) early enough to go by car to Naples.

Things to do in Amalfi

Outdoors · Historic Sites · Parks · Tours

Side Trips

Find places to stay Oct 5 — 9:
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Naples

— 3 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Change things up with these side-trips from Naples: Villa dei Misteri (in Pompeii) and Salerno (Promenade Trieste, Duomo di Salerno, &more). Next up on the itinerary: explore the ancient world of Pompeii Archaeological Park, make a trip to Piazza del Plebiscito, take in the architecture and atmosphere at Cloister of Santa Chiara, and examine the collection at Museo Archeologico Nazionale di Napoli.

For more things to do, where to stay, other places to visit, and tourist information, you can read our Naples trip itinerary planner.

Traveling by car from Amalfi to Naples takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Plan for slightly colder nights when traveling from Amalfi in October since evenings lows in Naples dip to 17°C. Finish your sightseeing early on the 12th (Wed) so you can take a train to Rome.

Things to do in Naples

Historic Sites · Museums · Parks

Side Trips

Find places to stay Oct 9 — 12:
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Rome

— 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, and museums. Your trip includes some of its best attractions: admire the striking features of Pantheon, pause for some serene contemplation at St. Peter's Basilica, admire the masterpieces at Vatican Museums, and delve into the distant past at Palatine Hill.

To find photos, reviews, maps, and tourist information, read Rome trip itinerary planning tool.

Traveling by train from Naples to Rome takes 2 hours. Alternatively, you can drive; or fly. In October, daily temperatures in Rome can reach 26°C, while at night they dip to 15°C. Finish your sightseeing early on the 17th (Mon) so you can drive to Assisi.

Things to do in Rome

Side Trip

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Assisi

— 3 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
You'll find plenty of places to visit near Assisi: Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti (in Perugia) and Montioni Frantoio e Cantina (in Montefalco). The adventure continues: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, take in the spiritual surroundings of Eremo delle Carceri, do a tasting at Azienda Agraria Saio, and walk around Mount Subasio.

To find ratings, more things to do, reviews, and other tourist information, read Assisi trip planner.

You can drive from Rome to Assisi in 2.5 hours. Other options are to take a train; or take a bus. In October, daily temperatures in Assisi can reach 24°C, while at night they dip to 12°C. Wrap up your sightseeing on the 20th (Thu) to allow time to drive to Siena.

Things to do in Assisi

Wineries · Historic Sites · Museums · Parks

Side Trips

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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.
Step out of Siena with an excursion to Ciacci Piccolomini d'Aragona in Castelnuovo dell'Abate--about 1h 5 min away. And it doesn't end there: deepen your understanding at Scuola di Cucina di Lella, make a trip to Centro Storico di Siena, take in the architecture and atmosphere at Basilica Cateriniana San Domenico, and get a sense of history and politics at Palazzo Pubblico and Museo Civico.

To see ratings, more things to do, where to stay, and tourist information, refer to the Siena online visit planner.

You can drive from Assisi to Siena in 2 hours. Alternatively, you can take a bus; or take a train. In October, daily temperatures in Siena can reach 26°C, while at night they dip to 15°C. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to Florence.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trip

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Florence

— 4 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Venture out of the city with trips to Castello del Trebbio (in Santa Brigida) and Leaning Tower of Pisa (in Pisa). There's lots more to do: admire the masterpieces at Florence Academy of Fine Arts, get to know the fascinating history of Piazza del Duomo, don't miss a visit to Piazzale Michelangelo, and snap pictures at Ponte Vecchio.

To find traveler tips, other places to visit, reviews, and other tourist information, use the Florence travel route tool.

You can drive from Siena to Florence in 1.5 hours. Other options are to take a bus; or take a train. October in Florence sees daily highs of 25°C and lows of 14°C at night. Finish up your sightseeing early on the 27th (Thu) so you can catch the train to Verona.

Things to do in Florence

Historic Sites · Museums · Wineries · Tours

Side Trips

Find places to stay Oct 23 — 27:
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Verona

— 2 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.
On the 28th (Fri), indulge in some culinary diversions at a local gastronomic tour, admire the striking features of Arche Scaligere, then take in panoramic vistas at Torre dei Lamberti, then wander the streets of Piazza delle Erbe, and finally contemplate the long history of I Portoni della Bra. Get ready for a full day of sightseeing on the 29th (Sat): enjoy some music at Arena di Verona, don't miss a visit to Piazza Bra, then explore the historical opulence of Museo di Castelvecchio, then take in the architecture and atmosphere at Basilica di San Zeno Maggiore, and finally admire the landmark architecture of Casa di Giulietta.

To find more things to do, where to stay, photos, and other tourist information, refer to the Verona trip itinerary maker website.

You can take a train from Florence to Verona in 2.5 hours. Alternatively, you can drive. Traveling from Florence in October, expect nights in Verona to be about the same, around 11°C, while days are little chillier, around 22°C. Wrap up your sightseeing on the 29th (Sat) early enough to drive to Milan.

Things to do in Verona

Historic Sites · Tours · Neighborhoods · Museums
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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 30th (Sun): admire the striking features of Galleria Vittorio Emanuele II, contemplate in the serene atmosphere at Duomo di Milano, then take an in-depth tour of Pinacoteca Ambrosiana, and finally explore the galleries of Basilica di Sant'Ambrogio. Keep things going the next day: take in the local highlights with Walking tours and then see La Casa Maledetta.

Planning Milan trip won't be overwhelming when you use Inspirock's itinerary maker.

Traveling by car from Verona to Milan takes 2 hours. Alternatively, you can take a train. In October, daytime highs in Milan are 21°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 31st (Mon) to allow time to fly back home.

Things to do in Milan

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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.