21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy vacation builder

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Route & dates

21 days in Italy Itinerary

Start: Chicago
Fly:  15​h
1
Naples
— 2 nights
Drive:  1​h 15​min
2
Furore
— 4 nights
car and train:  6​h
3
Florence
— 2 nights
Drive:  1​h 30​min
4
Arezzo
— 5 nights
Drive:  1​h 45​min
5
Pisa
— 4 nights
train:  3​h
6
Milan
— 1 night
Fly:  14​h 45​min
End: Chicago

2
nights
Naples

Naples
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. To find photos, where to stay, traveler tips, and other tourist information, you can read our Naples travel route site .

Chicago, USA to Naples is an approximately 14-hour combination of flight and train. You can also fly; or do a combination of flight and bus. The time zone difference moving from Central Standard Time to Central European Time is 7 hours. In October, Naples is a bit warmer than Chicago - with highs of 74°F and lows of 58°F. You will leave for Furore on the 16th (Wed).

Things to do in Naples

Tours Outdoors Historic Sites
Find places to stay Oct 14 — 16:

4
nights
Furore

Furore ©
Furore is a town and comune in the province of Salerno in the Campania region of south-western Italy. Get outdoors at Ravello-Minori Walk and Ravello - Atrani Walk. Get some historical perspective at Centro Storico Ravello and Castello di San Nicola de Thoro-Plano. Get out of town with these interesting Furore side-trips: Grotte di Castelcivita (in Castelcivita) and Ceramiche Cosmolena di Margherita di Palma (in Ravello). It doesn't end there: appreciate the history behind Fontana sant'Andrea.

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

You can drive from Naples to Furore in 1.5 hours. In October, plan for daily highs up to 73°F, and evening lows to 63°F. On the 20th (Sun), you're off toFlorence.

Things to do in Furore

Parks Trails Outdoors

Side Trips

Ravello, Castello di San Nicola de Thoro-Plano, Grotte di Castelcivita, Fontana sant'Andrea
Find places to stay Oct 16 — 20:
Highlights from your plan
Ravello - Atrani Walk ©
Ravello - Atrani Walk
Castello di San Nicola de Thoro-Plano ©

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Start off your visit on the 20th (Sun): admire the landmark architecture of The Baptistery of St. John and then contemplate the long history of Loggia dei Lanzi. On the 21st (Mon), you'll have a packed day of sightseeing: get engrossed in the history at Basilica di Santa Croce, see the interesting displays at Academy Of Florence Art Gallery, take in the views from Ponte Vecchio, make a trip to Piazzale Michelangelo, then get great views at Basilica San Miniato al Monte, and finally take in the architecture and atmosphere at Cathedral of Santa Maria del Fiore.

To find photos, ratings, where to stay, and other tourist information, use the Florence trip itinerary planning app .

Getting from Furore to Florence by car takes about 6 hours. Other options: do a combination of car and flight. Traveling from Furore in October, plan for slightly colder nights in Florence, with lows around 54°F. Wrap up your sightseeing by early afternoon on the 22nd (Tue) to allow time for the car ride to Arezzo.

Things to do in Florence

Historic Sites Museums

Side Trip

Castello di Monteriggioni
Find places to stay Oct 20 — 22:
Highlights from your plan
The Baptistery of St. John ©
The Baptistery of St. John
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©

5
nights
Arezzo

Arezzo ©
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Popular historic sites such as Duomo San Donato and San Domenico Church are in your itinerary. Winery Solaria Patrizia Cencioni and Poggio Rubino are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Arezzo: Sansepolcro (Museo Civico di Sansepolcro & Cattedrale di san Giovanni Evangelista), Anghiari (in Anghiari) and Cantalici (in Gaiole in Chianti). The adventure continues: take in the spiritual surroundings of San Francesco, Arezzo, see the interesting displays at Ivan Bruschi House & Museum, pause for some serene contemplation at Chiesa dei SS Michele e Adriano, and explore the world behind art at Museo Madonna del Parto.

To find where to stay, more things to do, maps, and other tourist information, you can read our Arezzo trip site .

Traveling by car from Florence to Arezzo takes 1.5 hours. Alternatively, you can take a train; or take a bus. Wrap up your sightseeing on the 27th (Sun) early enough to drive to Pisa.

Things to do in Arezzo

Museums Historic Sites Wineries

Side Trips

Sansepolcro, Montalcino, Cantalici, Museo Madonna del Parto, Anghiari
Find places to stay Oct 22 — 27:
Highlights from your plan
Anghiari ©
Anghiari
Duomo San Donato ©
Duomo San Donato
Winery Solaria Patrizia Cencioni ©
Winery Solaria Patrizia Cencioni

4
nights
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Give yourself a bit of retail therapy at Borgo Stretto and Corso Italia. Popular historic sites such as Duomo di Pisa and Battistero are in your itinerary. Explore Pisa's surroundings by going to Sacro Monte San Vivaldo (in San Vivaldo) and Volterra (Cathedral of Santa Maria Assunta & Palazzo Viti). There's still lots to do: contemplate the long history of Camposanto, admire the landmark architecture of Leaning Tower of Pisa, get to know the fascinating history of Piazza Martiri della Liberta, and explore the galleries of Museo Nazionale della Certosa Monumentale di Calci.

To find reviews, more things to do, maps, and more tourist information, refer to the Pisa trip planner.

Drive from Arezzo to Pisa in 2 hours. Alternatively, you can take a train. October in Pisa sees daily highs of 71°F and lows of 54°F at night. Wrap up your sightseeing on the 31st (Thu) to allow time to take a train to Milan.

Things to do in Pisa

Historic Sites Museums Neighborhoods

Side Trips

Volterra, Sacro Monte San Vivaldo, Museo Nazionale della Certosa Monumentale di Calci
Find places to stay Oct 27 — 31:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Battistero ©
Battistero
Knights’ Square ©
Knights’ Square

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.
Start off your visit on the 31st (Thu): take in the spiritual surroundings of Duomo di Milano, then steep yourself in history at Certosa di Pavia, and then take in the architecture and atmosphere at Chiesa di Santa Maria presso San Satiro.

To find ratings, reviews, photos, and tourist information, read Milan road trip planning site .

Getting from Pisa to Milan by train takes about 3 hours. Other options: drive; or fly. While traveling from Pisa, expect slightly colder days and about the same nights in Milan, ranging from highs of 65°F to lows of 52°F. Wrap up your sightseeing on the 1st (Fri) to allow time to travel back home.

Things to do in Milan

Historic Sites

Side Trips

Bergamo, Certosa di Pavia
Find places to stay Oct 31 — Nov 1:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Certosa di Pavia ©
Certosa di Pavia

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