33 days in Italy Itinerary

33 days in Italy Itinerary

Created using Inspirock Italy route maker

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Route & dates

33 days in Italy Itinerary

Start: Vancouver
Fly:  15​h 30​min
1
Milan
— 1 night
train:  1​h 15​min
2
Verona
— 3 nights
train:  1​h 45​min
3
Florence
— 4 nights
bus:  1​h 15​min
4
Siena
— 4 nights
Drive:  1​h 45​min
5
Assisi
— 2 nights
Drive:  4​h 30​min
6
Amalfi
— 3 nights
taxi + subway:  1​h 30​min
7
Naples
— 4 nights
train:  1​h 15​min
8
Rome
— 5 nights
Fly:  3​h 15​min
9
Venice
— 5 nights
Fly:  14​h 45​min
End: Vancouver

1
night
Milan

Milan ©
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.
On the 19th (Thu), get engrossed in the history at Pinacoteca Ambrosiana, take in the spiritual surroundings of Chiesa di San Maurizio al Monastero Maggiore, then take in the architecture and atmosphere at Duomo di Milano, and finally make a trip to Galleria Vittorio Emanuele II. Get ready for a full day of sightseeing on the 20th (Fri): stroll the grounds of Monumental Cemetery, then step into the grandiose world of Castello Sforzesco, and then admire the masterpieces at Pinacoteca di Brera.

To find reviews, other places to visit, more things to do, and tourist information, read Milan holiday website .

Vancouver, Canada to Milan is an approximately 15.5-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. Due to the time zone difference, you'll lose 9 hours traveling from Vancouver to Milan. When traveling from Vancouver in September, plan for a bit warmer days in Milan, with highs around 28°C, while nights are about the same with lows around 16°C. Finish your sightseeing early on the 20th (Fri) so you can take a train to Verona.

Things to do in Milan

Museums Historic Sites Shopping
Find places to stay Sep 19 — 20:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

3
nights
Verona

Verona ©
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.
Verona is known for nightlife, historic sites, nature, museums, and parks. Your plan includes some of its best attractions: experience the emotional art of opera at Arena di Verona, admire the sheer force of Parco Naturalistico delle Cascate-Family, indulge your senses at some of the top wineries in the area, and step into the grandiose world of Museo di Castelvecchio.

For other places to visit, photos, traveler tips, and tourist information, read our Verona trip planner .

Traveling by train from Milan to Verona takes 1.5 hours. Alternatively, you can drive. In September, daytime highs in Verona are 30°C, while nighttime lows are 17°C. Finish your sightseeing early on the 23rd (Mon) to allow enough time to take a train to Florence.

Things to do in Verona

Historic Sites Parks Tours
Find places to stay Sep 20 — 23:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore

4
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Leaning Tower of Pisa (in Pisa) and San Michele in Foro (in Lucca). Dedicate the 27th (Fri) to wine at some of the top wineries in the area. There's lots more to do: admire the masterpieces at Uffizi Galleries, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, get great views at Piazzale Michelangelo, and get engrossed in the history at Basilica di Santa Croce.

For where to stay, maps, and tourist information, you can read our Florence holiday planner .

Getting from Verona to Florence by train takes about 2 hours. Other options: drive; or take a bus. September in Florence sees daily highs of 30°C and lows of 17°C at night. Wrap up your sightseeing on the 27th (Fri) to allow time to take a bus to Siena.

Things to do in Florence

Tours Historic Sites Museums

Side Trips

Leaning Tower of Pisa, San Michele in Foro
Find places to stay Sep 23 — 27:
Highlights from your plan
Wine Tours & Tastings
Uffizi Galleries ©
Uffizi Galleries
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

4
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You'll find plenty of places to visit near Siena: Orvieto (Duomo di Orvieto & Pozzo di San Patrizio), Cascate del Mulino (in Saturnia) and Guardastelle Vineyard (in San Gimignano). Next up on the itinerary: don't miss a visit to Piazza del Campo, browse the collection at Biblioteca Piccolomini, learn about winemaking at Ciacci Piccolomini d'Aragona, and explore the historical opulence of Palazzo Pubblico and Museo Civico.

You can plan Siena trip in no time by asking Inspirock to help create your itinerary.

You can take a bus from Florence to Siena in 1.5 hours. Alternatively, you can drive; or take a train. September in Siena sees daily highs of 32°C and lows of 19°C at night. Finish your sightseeing early on the 1st (Tue) so you can drive to Assisi.

Things to do in Siena

Historic Sites Wineries Museums

Side Trips

Montalcino, Orvieto, Arezzo, Guardastelle Vineyard, Cascate del Mulino
Find places to stay Sep 27 — Oct 1:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Piazza del Campo ©
Piazza del Campo
Siena Cathedral ©
Siena Cathedral

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 2nd (Wed): take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, explore the historical opulence of Rocca Maggiore, then pause for some serene contemplation at Basilica inferiore di San Francesco d'Assisi, then contemplate the long history of Basilica di Santa Chiara, and finally steep yourself in history at San Damiano. On the 3rd (Thu), you'll have a packed day of sightseeing: see the interesting displays at Perugina Chocolate Factory, admire the masterpieces at Galleria Nazionale dell'Umbria, make a trip to Fontana Maggiore, then examine the collection at Museo della Porziuncola, then contemplate in the serene atmosphere at Basilica di San Francesco, and finally contemplate in the serene atmosphere at Eremo delle Carceri.

For photos, where to stay, other places to visit, and tourist information, use the Assisi tour planner .

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. Traveling from Siena in October, plan for little chillier nights in Assisi, with lows around 12°C. Cap off your sightseeing on the 3rd (Thu) early enough to go by car to Amalfi.

Things to do in Assisi

Historic Sites Museums

Side Trips

Perugia, Basilica di San Francesco
Find places to stay Oct 1 — 3:
Highlights from your plan
Museo della Porziuncola ©
Museo della Porziuncola
Eremo delle Carceri ©
Eremo delle Carceri

3
nights
Amalfi

Amalfi ©
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.
Venture out of the city with trips to Positano (Chiesa di Santa Maria Assunta e Cripta Medievale & Fornillo). There's much more to do: take in the pleasant sights at Sentiero degli dei (Path of the Gods), see the interesting displays at Museo della Carta, admire the landmark architecture of Villa Rufolo, and admire the natural beauty at Villa Cimbrone Gardens.

To see maps, ratings, reviews, and more tourist information, use the Amalfi trip itinerary planning site .

Getting from Assisi to Amalfi by car takes about 4.5 hours. Other options: take a train; or do a combination of train and bus. Traveling from Assisi in October, plan for somewhat warmer nights in Amalfi, with lows around 20°C. Finish your sightseeing early on the 6th (Sun) so you can travel to Naples.

Things to do in Amalfi

Outdoors Parks Historic Sites

Side Trips

Ravello, Amalfi Coast, Positano
Find places to stay Oct 3 — 6:
Highlights from your plan
Fornillo ©
Fornillo
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You'll find plenty of places to visit near Naples: Villa dei Misteri (in Pompeii), Vietri sul Mare (Sol’Art Ceramiche & Le Vigne di Raito) and Salerno (Giardino della Minerva, Castello di Arechi, & more). And it doesn't end there: delve into the distant past at Pompeii Archaeological Park, admire the masterpieces at Museo Nazionale di Capodimonte, pause for some serene contemplation at Cloister of Santa Chiara, and steep yourself in history at Catacombe di San Gaudioso.

For traveler tips, where to stay, photos, and other tourist information, read Naples trip itinerary website .

Traveling by combination of taxi and subway from Amalfi to Naples takes 1.5 hours. Alternatively, you can drive; or take a bus. Expect little chillier evenings in Naples when traveling from Amalfi in October, with lows around 17°C. Finish your sightseeing early on the 10th (Thu) to allow enough time to take a train to Rome.

Things to do in Naples

Historic Sites Museums Parks

Side Trips

Salerno, Pompeii, Vietri sul Mare
Find places to stay Oct 6 — 10:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Pompeii Archaeological Park ©
Pompeii Archaeological Park

5
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Change things up with a short trip to Villa d'Este in Tivoli (about 48 minutes away). Next up on the itinerary: steep yourself in history at Colosseum, admire the striking features of Pantheon, don't miss a visit to Spanish Steps, and contemplate in the serene atmosphere at Vatican Museums.

To see other places to visit, ratings, traveler tips, and tourist information, read Rome trip planner .

Getting from Naples to Rome by train takes about 1.5 hours. Other options: drive; or take a bus. In October in Rome, expect temperatures between 26°C during the day and 15°C at night. Wrap up your sightseeing on the 15th (Tue) early enough to travel to Venice.

Things to do in Rome

Historic Sites Museums Tours

Side Trips

Vatican City, Villa d'Este
Find places to stay Oct 10 — 15:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

5
nights
Venice

Venice ©
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.
Explore the numerous day-trip ideas around Venice: Padua (Basilica di Sant’Antonio, Scrovegni Chapel, & more). There's much more to do: explore the activities along Canal Grande, take in panoramic vistas at St Mark's Campanile, admire the landmark architecture of Basilica di San Marco, and take in the architecture and atmosphere at San Giorgio Maggiore.

To find ratings, reviews, maps, and tourist information, go to the Venice trip planner.

Traveling by flight from Rome to Venice takes 3.5 hours. Alternatively, you can take a train; or drive. When traveling from Rome in October, plan for slightly colder days in Venice, with highs around 22°C, while nights are about the same with lows around 12°C. Finish your sightseeing early on the 20th (Sun) to allow enough time to travel back home.

Things to do in Venice

Historic Sites Tours Museums

Side Trip

Padua
Find places to stay Oct 15 — 20:
Highlights from your plan
Canal Grande ©
Canal Grande
St. Mark's Square ©
St. Mark's Square
Basilica di San Marco
Basilica di San Marco

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