57 days in Italy Itinerary

57 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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Route & dates

57 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Milan
— 3 nights
train:  1​h 15​min
2
Verona
— 6 nights
bus:  1​h 30​min
3
Venice
— 7 nights
train:  2​h 15​min
4
Florence
— 7 nights
bus:  1​h 15​min
5
Siena
— 6 nights
Drive:  1​h 45​min
6
Assisi
— 5 nights
Drive:  2​h 15​min
7
Rome
— 7 nights
train:  1​h 45​min
8
Salerno
— 7 nights
ferry:  1​h 30​min
9
Positano
— 7 nights
train + Fly:  14​h 45​min
End: Toronto

3
nights
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.
Explore Milan's surroundings by going to Oasi WWF del Bassone (in Como), Anything But Work (in Mandello del Lario) and Aquarium of Genoa (in Genoa). There's lots more to do: contemplate in the serene atmosphere at Duomo di Milano, explore the different monuments and memorials at Monumental Cemetery, admire the striking features of Galleria Vittorio Emanuele II, and admire the verdant scenery at Langhe landscapes UNESCO.

For where to stay, maps, photos, and other tourist information, refer to the Milan trip itinerary builder tool .

Toronto, Canada to Milan is an approximately 11.5-hour flight. You can also do a combination of ferry and flight; or do a combination of flight and train. Traveling from Toronto to Milan, you'll lose 6 hours due to the time zone difference. October in Milan sees daily highs of 21°C and lows of 13°C at night. Finish up your sightseeing early on the 21st (Mon) so you can catch the train to Verona.

Things to do in Milan

Parks Outdoors Trails

Side Trips

Aquarium of Genoa, Anything But Work, Langhe landscapes UNESCO, Oasi WWF del Bassone
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Aquarium of Genoa ©
Aquarium of Genoa

6
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.
Explore Verona's surroundings by going to Gardaland Park (in Castelnuovo del Garda), Lago di Garda (in Garda) and Pista Ciclabile Val Di Non (in Fondo). There's still lots to do: enjoy some music at Arena di Verona, explore the historical opulence of Museo di Castelvecchio, take in the awesome beauty at Gruppo Dolomitico Sciliar-Catinaccio, Latemar - UNESCO, and wander the streets of Piazza delle Erbe.

To find maps, other places to visit, more things to do, and other tourist information, read our Verona tour itinerary planner .

Traveling by train from Milan to Verona takes 1.5 hours. Alternatively, you can drive. Expect a daytime high around 22°C in October, and nighttime lows around 11°C. Finish your sightseeing early on the 27th (Sun) to allow enough time to take a bus to Venice.

Things to do in Verona

Parks Nature Theme Parks

Side Trips

Lago di Garda, Pista Ciclabile Val Di Non, Gruppo Dolomitico Sciliar-Catinaccio, Latemar - UNESCO, Gardaland Park
Highlights from your plan
Lago di Garda ©
Lago di Garda
Gardaland Park ©
Gardaland Park
Arena di Verona ©
Arena di Verona

7
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 (Casa Ezzelino, Scrovegni Chapel, & more) and No Exit (in Udine). There's much more to do: contemplate the waterfront views at Canal Grande, admire the masterpieces at Peggy Guggenheim Collection, capture your vacation like a pro with an inspiring photography tour, and don't miss a visit to Piazza San Marco.

For ratings, traveler tips, maps, and more tourist information, read our Venice planning tool .

Traveling by bus from Verona to Venice takes 1.5 hours. Alternatively, you can drive; or take a shuttle. In October, daily temperatures in Venice can reach 22°C, while at night they dip to 12°C. Wrap up your sightseeing on the 3rd (Sun) early enough to take a train to Florence.

Things to do in Venice

Historic Sites Museums Tours

Side Trips

Padua, No Exit
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco

7
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Change things up with these side-trips from Florence: Castello del Trebbio (in Santa Brigida) and Leaning Tower of Pisa (in Pisa). There's still lots to do: explore the world behind art at Gallerie Degli Uffizi, appreciate the extensive heritage of Piazza del Duomo, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and examine the collection at Academy Of Florence Art Gallery.

To find traveler tips, photos, more things to do, and tourist information, refer to the Florence road trip planner.

Take a train from Venice to Florence in 2.5 hours. Alternatively, you can drive; or take a bus. November in Florence sees daily highs of 19°C and lows of 9°C at night. Wrap up your sightseeing on the 10th (Sun) to allow time to take a bus to Siena.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Leaning Tower of Pisa, Castello del Trebbio
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Campanile di Giotto ©
Campanile di Giotto
The Boboli Gardens ©
The Boboli Gardens

6
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: Castiglion del Bosco (in Montalcino), Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Guardastelle Vineyard (in San Gimignano). There's lots more to do: indulge your senses at some of the top wineries in the area, get lost in a book at Biblioteca Piccolomini, deepen your understanding at Scuola di Cucina di Lella, and explore the world behind art at Museo dell'Opera Metropolitana.

For other places to visit, maps, more things to do, and more tourist information, use the Siena road trip planning tool .

You can take a bus from Florence to Siena in 1.5 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 20°C in November, and nighttime lows around 10°C. Cap off your sightseeing on the 16th (Sat) early enough to go by car to Assisi.

Things to do in Siena

Tours Historic Sites Wineries

Side Trips

Montalcino, Guardastelle Vineyard, Val d'Orcia
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Nature & Wildlife Tours
Wine Tours & Tastings

5
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Get out of town with these interesting Assisi side-trips: Piana di Castelluccio di Norcia (in Castelluccio di Norcia), Museo Cinema a Pennello (in Montecosaro) and Montioni Frantoio e Cantina (in Montefalco). There's still lots to do: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, get to know the fascinating history of Centro Storico, contemplate in the serene atmosphere at San Damiano, and do a tasting at Tili Vini Societa Agricola.

To see ratings, more things to do, photos, and other tourist information, you can read our Assisi vacation planner.

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. Expect a bit cooler weather when traveling from Siena in November: highs in Assisi hover around 17°C, while lows dip to 7°C. Wrap up your sightseeing on the 21st (Thu) to allow time to drive to Rome.

Things to do in Assisi

Historic Sites Wineries Parks

Side Trips

Museo Cinema a Pennello, Montioni Frantoio e Cantina, Piana di Castelluccio di Norcia, Castello Monte Vibiano Vecchio
Highlights from your plan
Piana di Castelluccio di Norcia ©
Piana di Castelluccio di Norcia
Rocca Maggiore ©
Rocca Maggiore
Monte Subasio ©
Monte Subasio

7
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: contemplate the long history of Colosseum, explore the ancient world of Palatine Hill, take in the architecture and atmosphere at Pantheon, and explore the world behind art at Vatican Museums.

To find maps, ratings, where to stay, and tourist information, read our Rome travel itinerary planner.

Getting from Assisi to Rome by car takes about 2.5 hours. Other options: take a train; or take a bus. In November, daytime highs in Rome are 20°C, while nighttime lows are 9°C. Finish your sightseeing early on the 28th (Thu) so you can take a train to Salerno.

Things to do in Rome

Historic Sites Museums Parks

Side Trip

Vatican City
Highlights from your plan
Colosseum ©
Colosseum
Trevi Fountain ©
Trevi Fountain
Palatine Hill ©
Palatine Hill

7
nights
Salerno

Salerno ©
While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
Change things up with these side-trips from Salerno: Monte Finestra (in Tramonti), Ravello (Ravello - Atrani Walk & Ceramiche Cosmolena di Margherita di Palma) and Spiaggia Lannio (in Cetara). There's still lots to do: steep yourself in history at Pompeii Archaeological Park, hike along Sentiero dei Limoni, enjoy the sand and surf at Marina Di Vietri, and head outdoors with Chalet de Mar.

Find out how to plan Salerno trip without stress by asking Inspirock to help create an itinerary.

Getting from Rome to Salerno by train takes about 2 hours. Other options: drive; or take a bus. Traveling from Rome in November, expect somewhat warmer with lows of 17°C in Salerno. Wrap up your sightseeing on the 5th (Thu) to allow time to ride a ferry to Positano.

Things to do in Salerno

Outdoors Parks Beaches

Side Trips

Vietri sul Mare, Ravello, Minori, Food Tours, Sentiero dei Limoni
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Sentiero dei Limoni ©
Sentiero dei Limoni

7
nights
Positano

Positano ©
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Venture out of the city with trips to Ravello (Duomo di Ravello, Villa Rufolo, & more), Amalfi (Wine Tours & Tastings, Valle delle Ferriere, & more) and Lido di Ravello (in Castiglione). Next up on the itinerary: kick back and relax at Fornillo, admire the verdant scenery at Valle dei Mulini, Head underground at Grotte di Suppraiano, and have fun at Tennis Al Settimo Piano.

To find photos, traveler tips, and other tourist information, read Positano tour planner.

Traveling by ferry from Salerno to Positano takes 1.5 hours. Alternatively, you can do a combination of train and taxi; or drive. Expect a daytime high around 17°C in December, and nighttime lows around 12°C. Wrap up your sightseeing by early afternoon on the 12th (Thu) to allow time for travel back home.

Things to do in Positano

Outdoors Parks Tours

Side Trips

Amalfi, Praiano, Ravello
Highlights from your plan
Fornillo ©
Fornillo
Lido di Ravello ©
Lido di Ravello
Fishing Charters & Tours

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