26 days in Northwest Italy Itinerary

26 days in Northwest Italy Itinerary

Created using Inspirock Northwest Italy holiday planner

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Route & dates

26 days in Northwest Italy Itinerary

Start: Portland
Fly:  16 h
1
Venice
— 3 nights
Bus:  1 h 30 min
2
Verona
— 3 nights
Train:  1 h 15 min
3
Milan
— 2 nights
Train:  1 h 45 min
4
Florence
— 4 nights
Bus:  1 h 15 min
5
Siena
— 4 nights
Drive:  1 h 45 min
6
Assisi
— 3 nights
Drive:  2 h 15 min
7
Rome
— 5 nights
Fly:  17 h
End: Portland

3
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.
Venture out of the city with trips to Padua (Scrovegni Chapel & Basilica di Sant’Antonio). Next up on the itinerary: explore the activities along Canal Grande, snap pictures at Ponte dei Sospiri, admire the striking features of Basilica di San Marco, and examine the collection at Doge's Palace.

To find more things to do, maps, ratings, and tourist information, use the Venice vacation maker tool.

Portland, USA to Venice is an approximately 16- hour flight. You can also do a combination of flight and train; or do a combination of train and flight. You'll lose 9 hours traveling from Portland to Venice due to the time zone difference. In September, daytime highs in Venice are 77°F, while nighttime lows are 59°F. Finish up your sightseeing early on the 2nd (Fri) so you can catch the bus to Verona.

Things to do in Venice

Historic Sites Museums Parks

Side Trip

Padua
Find places to stay Sep 29 — Oct 2:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Piazza San Marco ©
Piazza San Marco

3
nights
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.
Go for a jaunt from Verona to Garda to see Lago di Garda about 1h 20 min away. There's still lots to do: enjoy some music at Arena di Verona, indulge your senses at some of the top wineries in the area, enjoy breathtaking views from Torre dei Lamberti, and visit Quinzano.

For ratings, reviews, traveler tips, and more tourist information, read Verona travel itinerary planner.

Getting from Venice to Verona by bus takes about 1.5 hours. Other options: drive; or take a shuttle. In October, daytime highs in Verona are 66°F, while nighttime lows are 50°F. Cap off your sightseeing on the 5th (Mon) early enough to catch the train to Milan.

Things to do in Verona

Tours Historic Sites Parks

Side Trip

Lago di Garda
Find places to stay Oct 2 — 5:
Highlights from your plan
Wine Tours & Tastings
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe

2
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.
Kick off your visit on the 6th (Tue): browse the different shops at Galleria Vittorio Emanuele II, take in the spiritual surroundings of Duomo di Milano, then admire the masterpieces at Pinacoteca Ambrosiana, and finally stroll the grounds of Monumental Cemetery. On your second day here, browse the fresh offerings at Micromercato Moltrasio, get outside with Aero Club Monte Cornizzolo, and then step into the grandiose world of Castello Sforzesco.

To see reviews, traveler tips, maps, and more tourist information, go to the Milan day trip tool.

Take a train from Verona to Milan in 1.5 hours. Alternatively, you can drive. October in Milan sees daily highs of 65°F and lows of 52°F at night. Wrap up your sightseeing on the 7th (Wed) to allow time to take a train to Florence.

Things to do in Milan

Historic Sites Museums Shopping

Side Trips

Aero Club Monte Cornizzolo, Micromercato Moltrasio
Find places to stay Oct 5 — 7:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

4
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for museums, historic sites, and shopping. Your plan includes some of its best attractions: explore the world behind art at Academy Of Florence Art Gallery, take in the spiritual surroundings of The Baptistery of St. John, steep yourself in history at Basilica of Santa Croce, and awaken your taste buds at some of the top wineries in the area.

For other places to visit, traveler tips, photos, and other tourist information, read Florence sightseeing app.

Traveling by train from Milan to Florence takes 2 hours. Alternatively, you can drive; or fly. When traveling from Milan in October, plan for a bit warmer days and about the same nights in Florence: temperatures range from 71°F by day to 54°F at night. Finish your sightseeing early on the 11th (Sun) to allow enough time to take a bus to Siena.

Things to do in Florence

Tours Museums Historic Sites
Find places to stay Oct 7 — 11:
Highlights from your plan
Food Tours
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

4
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore the numerous day-trip ideas around Siena: Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate), Winery Solaria Patrizia Cencioni (in Montalcino) and Guardastelle Vineyard (in San Gimignano). There's still lots to do: awaken your taste buds at some of the top wineries in the area, gain insight at Scuola di Cucina di Lella, get a sense of history and politics at Palazzo Pubblico and Museo Civico, and don't miss a visit to Centro Storico di Siena.

For where to stay, other places to visit, maps, and more tourist information, use the Siena attractions planning site.

Traveling by bus from Florence to Siena takes 1.5 hours. Alternatively, you can drive; or take a train. In October in Siena, expect temperatures between 73°F during the day and 56°F at night. Cap off your sightseeing on the 15th (Thu) early enough to go by car to Assisi.

Things to do in Siena

Historic Sites Wineries Tours

Side Trips

Montalcino, Guardastelle Vineyard
Find places to stay Oct 11 — 15:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Guardastelle Vineyard ©
Guardastelle Vineyard

3
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: Montioni Frantoio e Cantina (in Montefalco) and Vineria del Carmine (in La Bruna). There's lots more to do: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, walk around Mount Subasio, learn about winemaking at Tili Vini Societa Agricola, and take in the spiritual surroundings of Eremo delle Carceri.

For where to stay, reviews, maps, and other tourist information, go to the Assisi travel route planning site.

Drive from Siena to Assisi in 2 hours. Alternatively, you can take a bus; or take a train. Expect little chillier evenings in Assisi when traveling from Siena in October, with lows around 51°F. Finish up your sightseeing early on the 18th (Sun) so you can go by car to Rome.

Things to do in Assisi

Wineries Historic Sites Museums

Side Trips

Vineria del Carmine, Montioni Frantoio e Cantina
Find places to stay Oct 15 — 18:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

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.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: delve into the distant past at Colosseum, take in the architecture and atmosphere at Pantheon, admire the masterpieces at Galleria Borghese, and contemplate the long history of St. Peter's Basilica.

For maps, more things to do, traveler tips, and other tourist information, read our Rome trip itinerary builder app.

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. October in Rome sees daily highs of 73°F and lows of 55°F at night. Finish up your sightseeing early on the 23rd (Fri) so you can travel back home.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Oct 18 — 23:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

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