35 days in Southern Italy & Northwest Italy Itinerary

35 days in Southern Italy & Northwest Italy Itinerary

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Route & dates

35 days in Southern Italy & Northwest Italy Itinerary

Start: Toronto
Fly + train:  12​h 45​min
1
Naples
— 2 nights
Drive:  30​min
2
Castellammare Di Stabia
— 3 nights
bus:  45​min
3
Praiano
— 4 nights
train:  3​h
4
Rome
— 7 nights
train:  1​h 45​min
5
Florence
— 7 nights
Drive:  2​h 30​min
6
Cinque Terre
— 2 nights
train:  3​h
7
Milan
— 4 nights
train:  2​h 30​min
8
Venice
— 4 nights
Fly:  11​h 15​min
End: Toronto

2
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Kick off your visit on the 16th (Wed): explore the world behind art at Museo Cappella Sansevero, then steep yourself in history at Catacombe di San Gaudioso, then engage your brain at Museo delle Arti Sanitarie, and finally see the interesting displays at Museo Archeologico Nazionale di Napoli. On your second day here, take in the spiritual surroundings of San Domenico Maggiore, make a trip to Via San Gregorio Armeno, explore the galleries of The Neapolis Buried, then explore the world behind art at Museo Diocesano Napoli - Complesso Monumentale Donnaregina, then contemplate in the serene atmosphere at Pio Monte della Misericordia, and finally see the interesting displays at Museo Nazionale Ferroviario di Pietrarsa.

Ask Inspirock to suggest an itinerary and make planning a trip to Naples fast, fun, and easy.

Toronto, Canada to Naples is an approximately 13-hour combination of flight and train. You can also fly; or do a combination of ferry and flight. You'll lose 6 hours traveling from Toronto to Naples due to the time zone difference. Prepare for a bit warmer weather when traveling from Toronto in October: high temperatures in Naples hover around 27°C and lows are around 17°C. On the 18th (Fri), you'll have the morning to explore before heading off to Castellammare Di Stabia.

Things to do in Naples

Historic Sites Museums Childrens Museums
Highlights from your plan
Catacombe di San Gaudioso ©
Catacombe di San Gaudioso
The Neapolis Buried ©
The Neapolis Buried

3
nights
Castellammare Di Stabia

Castellammare Di Stabia ©
Castellammare di Stabia is a comune in the Metropolitan City of Naples, Campania region, in Italy. Take a break from the city and head to Bagno Conte and Parco Regionale dei Monti Lattari. Get some historical perspective at Castello di Lettere and Casa del Poeta Tragico. Explore Castellammare Di Stabia's surroundings by going to Santuario di San Michele Arcangelo e Santa Maria del Monte (in Maddaloni), Pompeii (Villa di Giulia Felice, Casa di Ottavio Quartione, & more) and Presepe Artistico (in Cava De' Tirreni). And it doesn't end there: delve into the distant past at Villa San Marco, admire the striking features of House of the Vettii, contemplate the long history of Villa Arianna, and explore the historical opulence of Castello Medioevale.

To find ratings, other places to visit, photos, and tourist information, read Castellammare Di Stabia trip itinerary maker app .

Castellammare Di Stabia is just a short distance from Naples. In October, daytime highs in Castellammare Di Stabia are 27°C, while nighttime lows are 17°C. On the 21st (Mon), wrap the sightseeing up by early afternoon so you can take a bus to Praiano.

Things to do in Castellammare Di Stabia

Historic Sites Parks Beaches

Side Trips

Pompeii, Presepe Artistico, Castello di Lettere, Santuario di San Michele Arcangelo e Santa Maria del Monte
Highlights from your plan
Castello Medioevale ©
Castello Medioevale
Castello di Lettere ©
Castello di Lettere
House of Venus in the Shell ©
House of Venus in the Shell

4
nights
Praiano

Praiano ©
Do some cultural sightseeing at Convento di Santa Maria a Castro and Church of Santa Maria Assunta. Take a break from the city and head to Fornillo and Spiaggia della Gavitella.

For where to stay, reviews, other places to visit, and more tourist information, go to the Praiano attractions planning site .

You can take a bus from Castellammare Di Stabia to Praiano in an hour. Alternatively, you can drive. Expect a daytime high around 26°C in October, and nighttime lows around 20°C. Cap off your sightseeing on the 25th (Fri) early enough to travel to Rome.

Things to do in Praiano

Outdoors Parks Beaches

Side Trip

Positano
Highlights from your plan
Walk of the Gods ©
Walk of the Gods
Fornillo ©
Fornillo
Kayaking & Canoeing

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.
Do some cultural sightseeing at Colosseum and Piazza Navona. Explore hidden gems such as Centro Storico Associazione Centro Storico and Cupola di San Pietro. Explore Rome's surroundings by going to Orvieto (Pozzo di San Patrizio & Duomo di Orvieto), Villa d'Este (in Tivoli) and Spoleto (Piazza del Duomo & Cattedrale di Santa Maria Assunta Spoleto). And it doesn't end there: take in the architecture and atmosphere at Basilica Papale San Paolo fuori le Mura, contemplate in the serene atmosphere at Chiesa del Gesu, make a trip to St. Peter's Basilica, and steep yourself in history at Palatine Hill.

To see more things to do, ratings, traveler tips, and other tourist information, read our Rome sightseeing planner .

You can take a train from Praiano to Rome in 3 hours. Other options are to drive; or take a bus. Traveling from Praiano in October, you can expect nighttime temperatures to be a bit cooler in Rome, with lows of 15°C. Wrap up your sightseeing on the 1st (Fri) to allow time to take a train to Florence.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Vatican City, Orvieto, Spoleto, Villa d'Este
Highlights from your plan
Pantheon ©
Pantheon
Vatican Museums
Vatican Museums

7
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll explore and learn at Gallerie Degli Uffizi and Academy Of Florence Art Gallery. Popular historic sites such as Cathedral of Santa Maria del Fiore and Basilica San Miniato al Monte are in your itinerary. Explore Florence's surroundings by going to Duomo di Modena (in Modena), Bologna (Chiesa di Santa Maria della Vita & Basilica - Santuario di Santo Stefano) and San Gimignano (San Gimignano Bell Tower, Piazza della Cisterna, & more). There's much more to do: explore the historical opulence of Palazzo dei Priori, contemplate in the serene atmosphere at The Baptistery of St. John, take an in-depth tour of Corridoio Vasariano, and see the interesting displays at Pitti Palace.

To find maps, traveler tips, ratings, and more tourist information, refer to the Florence driving holiday tool .

Getting from Rome to Florence by train takes about 2 hours. Other options: drive; or fly. In November, daytime highs in Florence are 19°C, while nighttime lows are 9°C. Finish your sightseeing early on the 8th (Fri) so you can drive to Cinque Terre.

Things to do in Florence

Historic Sites Museums Childrens Museums

Side Trips

San Gimignano, Bologna, Biblioteca Piccolomini, Duomo di Modena, Palazzo dei Priori
Highlights from your plan
Piazzale Michelangelo ©
Piazzale Michelangelo
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

2
nights
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 9th (Sat), take in the architecture and atmosphere at Santa Margherita di Antiochia Church, step into the grandiose world of Castello Doria, tour the pleasant surroundings at Sentiero Monterosso - Vernazza, then take in the spiritual surroundings of Oratorio dei Disciplinati di Santa Caterina, then get to know the fascinating history of Borgo Storico di Corniglia, and finally take in the spiritual surroundings of Chiesa di San Lorenzo.

To see other places to visit, more things to do, ratings, and other tourist information, you can read our Cinque Terre journey planner.

You can drive from Florence to Cinque Terre in 2.5 hours. Alternatively, you can take a train. In November in Cinque Terre, expect temperatures between 19°C during the day and 9°C at night. Finish your sightseeing early on the 10th (Sun) so you can take a train to Milan.

Things to do in Cinque Terre

Historic Sites Parks Outdoors
Highlights from your plan
Santa Margherita di Antiochia Church ©
Borgo Storico di Corniglia ©
Borgo Storico di Corniglia
Chiesa di San Lorenzo ©
Chiesa di San Lorenzo

4
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.
Let the collections at Museo del Novecento and Museo Poldi Pezzoli capture your imagination. Eschew the tourist crowds and head to Duomo Vecchio di Brescia and Pinacoteca Ambrosiana. Explore the numerous day-trip ideas around Milan: Piazza Paolo VI (in Brescia) and Bergamo (Mura Venete & Cappella Colleoni). There's lots more to do: contemplate in the serene atmosphere at Duomo di Milano, see the interesting displays at Museo Della Scienza E Della Tecnologia Leonardo da Vinci, contemplate the long history of Il Cenacolo, and pause for some serene contemplation at Chiesa di San Bernardino alle Ossa.

For photos, other places to visit, where to stay, and other tourist information, you can read our Milan trip builder website .

Traveling by train from Cinque Terre to Milan takes 3 hours. Alternatively, you can drive. When traveling from Cinque Terre in November, plan for little chillier days and about the same nights in Milan: temperatures range from 15°C by day to 6°C at night. Finish up your sightseeing early on the 14th (Thu) so you can catch the train to Venice.

Things to do in Milan

Historic Sites Museums Childrens Museums

Side Trips

Bergamo, Brescia
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Museo del Novecento ©
Museo del Novecento

4
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.
Get a sense of the local culture at Doge's Palace and San Giorgio Maggiore. Explore hidden gems such as Cannaregio and Venetian Arsenal. There's much more to do: contemplate in the serene atmosphere at Scuola Grande di San Rocco, pause for some serene contemplation at Basilica dei Santi Giovanni e Paolo (San Zanipolo), admire the landmark architecture of Scala Contarini del Bovolo, and hit the best photo ops around with an inspiring photography tour.

For other places to visit, reviews, more things to do, and other tourist information, read Venice online trip itinerary maker .

You can take a train from Milan to Venice in 2.5 hours. Other options are to drive; or do a combination of flight and train. In November, daily temperatures in Venice can reach 15°C, while at night they dip to 7°C. On the 18th (Mon), you'll have the morning to explore before heading back home.

Things to do in Venice

Historic Sites Parks Nature
Highlights from your plan
San Giorgio Maggiore ©
San Giorgio Maggiore
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

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