22 days in Italy Itinerary

22 days in Italy Itinerary

Created using Inspirock Italy trip itinerary maker

This plan was created by another user.  Make it your plan

Route & dates

22 days in Italy Itinerary

Start: Chicago
Fly:  14​h 15​min
1
Milan
— 1 night
train:  45​min
2
Como
— 4 nights
Drive:  1​h 15​min
3
Introzzo
— 2 nights
Drive:  3​h
4
Bolzano
— 1 night
Drive:  4​h 30​min
5
Cinque Terre
— 3 nights
Drive:  2​h 30​min
6
Florence
— 4 nights
7
Venice
— 5 nights
Fly:  14​h
End: Chicago

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.
On the 13th (Sat), admire the striking features of Galleria Vittorio Emanuele II, explore the world behind art at Pinacoteca Ambrosiana, and then see the interesting displays at Castello Sforzesco. Keep things going the next day: stroll the grounds of Monumental Cemetery, then explore the world behind art at Pinacoteca di Brera, and then contemplate in the serene atmosphere at Duomo di Milano.

To see photos, more things to do, reviews, and more tourist information, read our Milan trip itinerary planning app .

Chicago, USA to Milan is an approximately 14.5-hour flight. You can also do a combination of flight and train; or do a combination of train and flight. The time zone difference moving from Central Standard Time (CST) to Central European Time (CET) is 7 hours. In October, daytime highs in Milan are 65°F, while nighttime lows are 52°F. Finish up your sightseeing early on the 14th (Sun) so you can catch the train to Como.

Things to do in Milan

Museums Historic Sites Shopping
Find places to stay Oct 13 — 14:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

4
nights
Como

Como ©
Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.
Venture out of the city with trips to Il Giardino della Valle (in Cernobbio), Villa del Balbianello (in Tremezzina) and Turati Centro Nautico Lario (in Argegno). There's lots more to do: look for all kinds of wild species at I Falconieri del Feudo, make a trip to Palazzo Terragni, pause for some serene contemplation at Cathedral of Como (Duomo), and head outdoors with Lake Como Adventures.

For other places to visit, ratings, reviews, and tourist information, read our Como tour app .

You can take a train from Milan to Como in an hour. Another option is to drive. October in Como sees daily highs of 64°F and lows of 49°F at night. Finish up your sightseeing early on the 18th (Thu) so you can travel to Introzzo.

Things to do in Como

Outdoors Parks Historic Sites

Side Trips

Villa del Balbianello, Il Giardino della Valle, Turati Centro Nautico Lario
Find places to stay Oct 14 — 18:
Highlights from your plan
Turati Centro Nautico Lario ©
Turati Centro Nautico Lario
Villa del Balbianello ©
Villa del Balbianello
I Falconieri del Feudo ©
I Falconieri del Feudo

2
nights
Introzzo

Introzzo ©
Start off your visit on the 19th (Fri): take in the awesome beauty at Monte Legnoncino and then take your sightseeing to a higher altitude at Monte Grona.

Quickly create a custom-made itinerary for Introzzo using our trip planner.

You can drive from Como to Introzzo in 1.5 hours. In October, plan for daily highs up to 63°F, and evening lows to 49°F. Finish your sightseeing early on the 20th (Sat) so you can travel to Bolzano.

Things to do in Introzzo

Nature Parks

Side Trip

Monte Grona
Find places to stay Oct 18 — 20:
Highlights from your plan
Monte Grona ©
Monte Grona
Monte Legnoncino ©
Monte Legnoncino

1
night
Bolzano

Bolzano ©
South Tyrol's capital, Bolzano, has been named the Italian city with the highest quality of life.
Kick off your visit on the 20th (Sat): admire all the interesting features of Kaserhof, then tour the pleasant surroundings at Puez-Geisler Nature Park, and then make a trip to Piazza Walther.

To see other places to visit, photos, reviews, and tourist information, read our Bolzano road trip planner.

Traveling by car from Introzzo to Bolzano takes 4 hours. In October, daytime highs in Bolzano are 66°F, while nighttime lows are 47°F. Wrap up your sightseeing on the 21st (Sun) early enough to drive to Cinque Terre.

Things to do in Bolzano

Parks

Side Trip

Kaserhof
Find places to stay Oct 20 — 21:
Highlights from your plan
Kaserhof ©
Kaserhof
Piazza Walther ©
Piazza Walther

3
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.
Cinque Terre is known for trails, shopping, historic sites, nature, and beaches. Your plan includes some of its best attractions: trek along Footpath Monterosso - Vernazza, appreciate the extensive heritage of Borgo Storico di Corniglia, learn about winemaking at Terra di Bargon, and pause for some serene contemplation at Convento dei Cappuccini e Chiesa di San Francesco.

For other places to visit, more things to do, where to stay, and more tourist information, you can read our Cinque Terre trip planner .

Traveling by car from Bolzano to Cinque Terre takes 4.5 hours. Alternatively, you can do a combination of train and car; or take a train. Traveling from Bolzano in October, expect somewhat warmer with lows of 54°F in Cinque Terre. Finish your sightseeing early on the 24th (Wed) to allow enough time to drive to Florence.

Things to do in Cinque Terre

Historic Sites Outdoors Parks
Find places to stay Oct 21 — 24:
Highlights from your plan
Cinque Terre Trails ©
Cinque Terre Trails
Footpath Monterosso - Vernazza ©
Footpath Monterosso - Vernazza

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll find plenty of places to visit near Florence: Siena Cathedral (in Siena) and Guardastelle Vineyard (in San Gimignano). Next up on the itinerary: admire the masterpieces at Uffizi Galleries, take in the spiritual surroundings of The Baptistery of St. John, get a sense of history and politics at Palazzo Vecchio, and take in the views from Ponte Vecchio.

Take the guesswork out of planning a Florence vacation by using our trip itinerary maker.

Getting from Cinque Terre to Florence by car takes about 2.5 hours. Other options: take a train. In October, plan for daily highs up to 71°F, and evening lows to 54°F. Wrap up your sightseeing on the 28th (Sun) early enough to take a train to Venice.

Things to do in Florence

Museums Historic Sites Parks

Side Trips

Guardastelle Vineyard, Siena Cathedral
Find places to stay Oct 24 — 28:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Uffizi Galleries ©
Uffizi Galleries
Galleria dell'Accademia ©
Galleria dell'Accademia

5
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 (Basilica di Sant’Antonio & Scrovegni Chapel). There's still lots to do: explore the activities along Canal Grande, admire the landmark architecture of Basilica di San Marco, see the interesting displays at Doge's Palace, and take in the local highlights with Walking tours.

To find more things to do, where to stay, maps, and tourist information, refer to the Venice trip builder .

Take a train from Florence to Venice in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Florence in October, expect nights in Venice to be about the same, around 51°F, while days are slightly colder, around 66°F. Wrap up your sightseeing on the 2nd (Fri) to allow time to travel back home.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay Oct 28 — Nov 2:
Highlights from your plan
Canal Grande ©
Canal Grande
St. Mark's Square
St. Mark's Square
Basilica di San Marco
Basilica di San Marco

Similar Plans

24 days in Italy & Prague BY A USER FROM AUSTRALIA May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 24 days in Italy BY A USER FROM MEXICO September, culture, relaxing, romantic, historic sites, popular & hidden gems PREFERENCES: September, culture, relaxing, romantic, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in Milan BY A USER FROM AUSTRALIA May, culture, outdoors, relaxing, beaches, historic sites, hidden gems PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 23 days in Italy BY A USER FROM UNITED STATES June, culture, relaxing, romantic, beaches, historic sites, popular & hidden gems PREFERENCES: June, culture, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Milan, Florence & Venice BY A USER FROM UNITED KINGDOM October, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: October, teens, kids, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in Italy BY A USER FROM BRAZIL September, culture, beaches, historic sites, museums, slow & easy, popular sights PREFERENCES: September, culture, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Slow & easy 6 days in Venice BY A USER FROM UNITED KINGDOM July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 11 days in Italy BY A USER FROM QATAR June, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, teens, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 18 days in Italy & London BY A USER FROM UNITED STATES July, teens, kids, culture, relaxing, beaches, historic sites, shopping, wildlife, popular & hidden gems PREFERENCES: July, teens, kids, culture, relaxing, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in Europe BY A USER FROM PORTUGAL July, culture, relaxing, beaches, museums, popular sights PREFERENCES: July, culture, relaxing, beaches, museums ATTRACTION STYLE: Popular sights PACE: Medium 28 days in Italy BY A USER FROM CANADA August, culture, outdoors, relaxing, romantic, beaches, historic sites, popular & hidden gems PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 8 days in Milan, Lake Como & Venice BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans