14 days in Italy Itinerary

14 days in Italy Itinerary

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Route & dates

14 days in Italy Itinerary

Start: Montreal
Fly:  12​h
1
Venice
— 2 nights
train:  2​h 30​min
2
Milan
— 1 night
train:  1​h 45​min
3
Florence
— 2 nights
Drive:  2​h 15​min
4
Assisi
— 1 night
Drive:  4​h 30​min
5
Ravello
— 3 nights
subway + train:  3​h
6
Rome
— 3 nights
Fly:  12​h
End: Montreal

2
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.
Venice is known for historic sites, parks, nightlife, museums, and shopping. Your plan includes some of its best attractions: contemplate the waterfront views at Canal Grande, admire the landmark architecture of Basilica di San Marco, admire the masterpieces at Gallerie dell'Accademia, and see the interesting displays at Doge's Palace.

To see ratings, traveler tips, more things to do, and other tourist information, read Venice trip planner.

Montreal, Canada to Venice is an approximately 12-hour flight. You can also do a combination of train and flight. You'll lose 6 hours traveling from Montreal to Venice due to the time zone difference. Expect a bit warmer temperatures when traveling from Montreal in October; daily highs in Venice reach 22°C and lows reach 12°C. Finish your sightseeing early on the 10th (Thu) so you can take a train to Milan.

Things to do in Venice

Historic Sites Museums Parks
Find places to stay Oct 7 — 10:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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.
Kick off your visit on the 11th (Fri): stroll the grounds of Monumental Cemetery, get engrossed in the history at Pinacoteca Ambrosiana, then take in the spiritual surroundings of Duomo di Milano, and finally admire the striking features of Galleria Vittorio Emanuele II.

To see ratings and other tourist information, read Milan day trip planner.

Traveling by train from Venice to Milan takes 2.5 hours. Alternatively, you can drive; or do a combination of train and flight. In October, daytime highs in Milan are 21°C, while nighttime lows are 13°C. Finish your sightseeing early on the 11th (Fri) to allow enough time to take a train to Florence.

Things to do in Milan

Historic Sites Museums Shopping
Find places to stay Oct 10 — 11:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 12th (Sat): take in the views from Ponte Vecchio, explore the world behind art at Gallerie Degli Uffizi, appreciate the extensive heritage of Piazza del Duomo, then take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, then take in the spiritual surroundings of Campanile di Giotto, and finally admire the striking features of Loggia dei Lanzi. Get ready for a full day of sightseeing on the next day: see the interesting displays at Pitti Palace, get great views at Piazzale Michelangelo, see the interesting displays at Academy Of Florence Art Gallery, then take an in-depth tour of Basilica di Santa Croce, and finally don't miss a visit to The Baptistery of St. John.

To find other places to visit, maps, ratings, and more tourist information, use the Florence trip itinerary planning website .

You can take a train from Milan to Florence in 2 hours. Other options are to drive; or fly. Traveling from Milan in October, expect nights in Florence to be about the same, around 14°C, while days are somewhat warmer, around 25°C. Finish your sightseeing early on the 13th (Sun) so you can drive to Assisi.

Things to do in Florence

Museums Historic Sites
Find places to stay Oct 11 — 13:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

1
night
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Start off your visit on the 14th (Mon): do a tasting at Tili Vini Societa Agricola, see the interesting displays at Museo della Porziuncola, take in the spiritual surroundings of Eremo delle Carceri, do a tasting at Bibenda Assisi, then take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and finally stroll around Mount Subasio.

For traveler tips, reviews, ratings, and more tourist information, read our Assisi trip itinerary tool .

Traveling by car from Florence to Assisi takes 2.5 hours. Alternatively, you can take a train. Expect a daytime high around 24°C in October, and nighttime lows around 12°C. Finish your sightseeing early on the 14th (Mon) so you can drive to Ravello.

Things to do in Assisi

Wineries Historic Sites Parks
Find places to stay Oct 13 — 14:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

3
nights
Ravello

Ravello ©
You'll find plenty of places to visit near Ravello: Monte Finestra (in Tramonti), I Suoni degli Dei - Pelagos (in Praiano) and Positano (Fornillo & Il Sentiero Degli Dei).

To see traveler tips, more things to do, ratings, and tourist information, refer to the Ravello vacation planner .

Getting from Assisi to Ravello 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, expect somewhat warmer with lows of 20°C in Ravello. Cap off your sightseeing on the 17th (Thu) early enough to travel to Rome.

Things to do in Ravello

Outdoors Parks Beaches

Side Trips

Positano, Praiano, Amalfi, Monte Finestra, Liquorificio Mansi Carlo
Find places to stay Oct 14 — 17:
Highlights from your plan
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei

3
nights
Rome

Rome ©
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, museums, classes, and shopping. Your plan includes some of its best attractions: delve into the distant past at Colosseum, explore the world behind art at Vatican Museums, get to know the fascinating history of Piazza Navona, and don't miss a visit to Roman Forum.

To see where to stay, reviews, photos, and more tourist information, you can read our Rome trip itinerary app .

Do a combination of subway and train from Ravello to Rome in 3 hours. Alternatively, you can drive; or do a combination of bus and train. Traveling from Ravello in October, expect a bit cooler with lows of 15°C in Rome. Finish your sightseeing early on the 20th (Sun) to allow enough time to travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Oct 17 — 20:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

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