17 days in Northwest Italy Itinerary

Created using Inspirock Northwest Italy holiday planner
Make it your trip
Fly
1
Milan
— 1 night
Drive
2
Portofino
— 1 night
Train
3
Cinque Terre
— 1 night
Train
4
Pisa
— 1 night
Drive
5
Florence
— 2 nights
Drive
6
Siena
— 3 nights
Drive
7
Assisi
— 1 night
Drive
8
Rome
— 3 nights
Fly
9
Verona
— 1 night
Drive
10
Venice
— 2 nights
Fly

S M T W T F S
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Milan — 1 night

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.
Start off your visit on the 7th (Thu): take an in-depth tour of Basilica di Sant'Ambrogio, explore the world behind art at Pinacoteca Ambrosiana, then contemplate in the serene atmosphere at Duomo di Milano, and finally admire the landmark architecture of Galleria Vittorio Emanuele II.

For photos, more things to do, and other tourist information, you can read our Milan road trip planner.

Toronto, Canada to Milan is an approximately 11.5-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from Toronto to Milan. Expect a daytime high around 28°C in September, and nighttime lows around 16°C. Wrap up your sightseeing on the 7th (Thu) early enough to drive to Portofino.
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Museums · Historic Sites · Shopping
Find places to stay Sep 6 — 7:

Portofino — 1 night

Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. On the 8th (Fri), get a new perspective on things with Boat Tours & Water Sports, then look for all kinds of wild species at Area Marina Protetta Portofino, then explore the historical opulence of Castello Brown, and finally take in the architecture and atmosphere at Parrocchia Di San Martino.

For reviews, ratings, traveler tips, and tourist information, refer to the Portofino travel itinerary planner.

Traveling by car from Milan to Portofino takes 2.5 hours. Alternatively, you can take a train. Plan for a bit warmer nights when traveling from Milan in September since evenings lows in Portofino dip to 22°C. Wrap up your sightseeing on the 8th (Fri) early enough to take a train to Cinque Terre.
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Historic Sites · Wildlife · Adventure · Outdoors
Find places to stay Sep 7 — 8:

Cinque Terre — 1 night

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Start off your visit on the 9th (Sat): contemplate in the serene atmosphere at Chiesa di San Lorenzo, head outdoors with 5 Terre Pelagos Boat Tours, then tour the pleasant surroundings at Cinque Terre footpaths, and finally get great views at View Point Corniglia.

To find more things to do, traveler tips, reviews, and tourist information, read Cinque Terre road trip planner.

You can take a train from Portofino to Cinque Terre in 1.5 hours. Alternatively, you can drive. Traveling from Portofino in September, plan for little chillier nights in Cinque Terre, with lows around 17°C. Finish your sightseeing early on the 9th (Sat) so you can take a train to Pisa.
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Outdoors · Tours · Wildlife · Historic Sites
Find places to stay Sep 8 — 9:

Pisa — 1 night

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Start off your visit on the 10th (Sun): contemplate the long history of Le mura di Lucca, admire the striking features of St Martin Cathedral, take in the spiritual surroundings of Duomo di Pisa, then make a trip to Piazza dei Miracoli, and finally make a trip to Leaning Tower of Pisa.

To find more things to do, traveler tips, ratings, and tourist information, you can read our Pisa day trip planning tool.

You can take a train from Cinque Terre to Pisa in 2 hours. Another option is to drive. In September, daytime highs in Pisa are 30°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 10th (Sun) early enough to drive to Florence.
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Historic Sites
Side Trip
Find places to stay Sep 9 — 10:

Florence — 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 11th (Mon), indulge your senses at Scenic wine tours in Tuscany, steep yourself in history at Cathedral of Santa Maria del Fiore, then get to know the fascinating history of Piazza del Duomo, and finally take in panoramic vistas at Campanile di Giotto. Keep things going the next day: don't miss a visit to Piazza della Signoria, snap pictures at Ponte Vecchio, don't miss a visit to Piazzale Michelangelo, then admire the masterpieces at Florence Academy of Fine Arts, and finally pause for some serene contemplation at Basilica of Santa Croce.

To see photos and more tourist information, you can read our Florence trip planner.

Traveling by car from Pisa to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. In September in Florence, expect temperatures between 30°C during the day and 17°C at night. Finish up your sightseeing early on the 12th (Tue) so you can go by car to Siena.
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Historic Sites · Wineries · Tours · Museums
Side Trip
Find places to stay Sep 10 — 12:

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.
Take a break from Siena with a short trip to Guardastelle Vineyard in San Gimignano, about 52 minutes away. There's much more to do: indulge your senses at some of the top wineries in the area, indulge in some culinary diversions at a local gastronomic tour, deepen your understanding at Scuola di Cucina di Lella, and contemplate in the serene atmosphere at San Francesco.

For more things to do, traveler tips, photos, and more tourist information, use the Siena trip builder site.

You can drive from Florence to Siena in 1.5 hours. Other options are to take a bus; or take a train. In September, daily temperatures in Siena can reach 32°C, while at night they dip to 19°C. Wrap up your sightseeing on the 15th (Fri) early enough to drive to Assisi.
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Tours · Wineries · Historic Sites · Museums
Side Trip
Find places to stay Sep 12 — 15:

Assisi — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 16th (Sat): do a tasting at Tili Vini Societa Agricola, contemplate in the serene atmosphere at Eremo delle Carceri, then step into the grandiose world of Rocca Maggiore, then take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, and finally learn about winemaking at Azienda Agraria Saio.

To see maps, other places to visit, ratings, and more tourist information, read Assisi trip builder.

You can drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. September in Assisi sees daily highs of 30°C and lows of 16°C at night. Finish your sightseeing early on the 16th (Sat) to allow enough time to drive to Rome.
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Historic Sites · Wineries
Find places to stay Sep 15 — 16:

Rome — 3 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, sightseeing, and nightlife. Your trip includes some of its best attractions: take in the architecture and atmosphere at St. Peter's Basilica, stop by Trastevere, steep yourself in history at Roman Forum, and explore the ancient world of Colosseum.

For other places to visit, traveler tips, and more tourist information, you can read our Rome trip planner.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. September in Rome sees daily highs of 32°C and lows of 18°C at night. Wrap up your sightseeing on the 19th (Tue) to allow time to fly to Verona.
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Historic Sites · Museums · Neighborhoods
Side Trip
Find places to stay Sep 16 — 19:

Verona — 1 night

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 20th (Wed), pause for some serene contemplation at Chiesa di San Zeno in Oratorio, step into the grandiose world of Museo di Castelvecchio, contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, then examine the collection at Casa di Giulietta, then take in the architecture and atmosphere at Cappella dei Notai, and finally enjoy breathtaking views from Torre dei Lamberti.

For more things to do, maps, other places to visit, and tourist information, use the Verona trip app.

Fly from Rome to Verona in 2.5 hours. Alternatively, you can take a train; or drive. In September, daytime highs in Verona are 30°C, while nighttime lows are 17°C. Finish up your sightseeing early on the 20th (Wed) so you can go by car to Venice.
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Historic Sites · Neighborhoods · Shopping · Museums
Find places to stay Sep 19 — 20:

Venice — 2 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.
Kick off your visit on the 21st (Thu): take in panoramic vistas at St Mark's Campanile, admire the landmark architecture of Basilica di San Marco, snap pictures at Ponte di Rialto, then explore the activities along Canal Grande, and finally contemplate the long history of Squero di San Trovaso. Get ready for a full day of sightseeing on the next day: take in the spiritual surroundings of Chiesa del Santissimo Redentore, steep yourself in history at Ponte dei Sospiri, get to know the fascinating history of Piazza San Marco, then see the interesting displays at Doge's Palace, and finally admire the masterpieces at Peggy Guggenheim Collection.

To see where to stay, maps, traveler tips, and other tourist information, you can read our Venice trip planner.

Getting from Verona to Venice by car takes about 1.5 hours. Other options: take a shuttle; or take a train. In September, plan for daily highs up to 29°C, and evening lows to 17°C. Wrap up your sightseeing on the 22nd (Fri) to allow time to fly back home.
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Historic Sites · Museums · Nature · Parks
Find places to stay Sep 20 — 22: