21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy journey planner

Make it your trip
Fly
1
Venice
— 3 nights
Drive
2
Canazei
— 1 night
Drive
3
Verona
— 1 night
Train
4
Bologna
— 1 night
Train
5
Florence
— 3 nights
Train
6
Rome
— 4 nights
Train
7
Naples
— 3 nights
Fly
8
Cinque Terre
— 3 nights
Drive
9
Milan
— 1 night
Fly

S M T W T F S
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13

Venice

— 3 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.
Venture out of the city with trips to Padua (Chiesa degli Eremitani - World Heritage Site, Scrovegni Chapel, &more). There's still lots to do: contemplate the waterfront views at Canal Grande, steep yourself in history at Ponte dei Sospiri, make a trip to Peggy Guggenheim Collection, and pick up a one of a kind souvenir at Gioielleria Eredi Jovon.

To find ratings, other places to visit, where to stay, and other tourist information, use the Venice road trip app.

New York City, USA to Venice is an approximately 11.5-hour flight. Traveling from New York City to Venice, you'll lose 6 hours due to the time zone difference. Traveling from New York City in October, expect little chillier with lows of 51°F in Venice. Wrap up your sightseeing on the 25th (Mon) early enough to drive to Canazei.

Things to do in Venice

Historic Sites · Museums · Parks · Nature

Side Trip

Find places to stay Oct 22 — 25:

Canazei

— 1 night
Canazei is a comune (municipality) in Trentino in the northern Italian region Trentino-Alto Adige/Südtirol, located in the upper part of the Val di Fassa, about 110km northeast of Trento. Kick off your visit on the 26th (Tue): take in the dramatic natural features at Seiser Alm, take your sightseeing to a higher altitude at Sass Pordoi, and then appreciate the history behind Monumento a Fausto Coppi.

For ratings, traveler tips, and other tourist information, refer to the Canazei trip planner.

You can drive from Venice to Canazei in 2.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 66°F, and evening lows to 47°F. Finish your sightseeing early on the 26th (Tue) so you can drive to Verona.

Things to do in Canazei

Parks · Nature · Outdoors · Trails

Side Trips

Find places to stay Oct 25 — 26:

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.
Kick off your visit on the 27th (Wed): make a trip to I Portoni della Bra, catch a live event at Arena di Verona, take a stroll through Piazza delle Erbe, browse the exhibits of Casa di Giulietta, then take in the architecture and atmosphere at Basilica di San Zeno Maggiore, and finally step into the grandiose world of Museo di Castelvecchio.

Plan my day in Verona using traveler tips and tourist information provided by Inspirock.

Getting from Canazei to Verona by car takes about 2.5 hours. Other options: take a shuttle; or do a combination of taxi and train. In October in Verona, expect temperatures between 66°F during the day and 50°F at night. Wrap up your sightseeing on the 27th (Wed) to allow time to take a train to Bologna.

Things to do in Verona

Historic Sites · Shopping · Neighborhoods · Museums
Find places to stay Oct 26 — 27:

Bologna

— 1 night

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Start off your visit on the 28th (Thu): admire the landmark architecture of Palazzo Comunale, get engrossed in the history at Museo Civico Medievale, then pause for some serene contemplation at Basilica - Santuario di Santo Stefano, then enjoy breathtaking views from Le Due Torri Torre degli Asinell, and finally admire the masterpieces at Pinacoteca Nazionale di Bologna.

For ratings, where to stay, and other tourist information, you can read our Bologna visit planner.

You can take a train from Verona to Bologna in 1.5 hours. Alternatively, you can drive; or take a bus. In October in Bologna, expect temperatures between 67°F during the day and 52°F at night. Wrap up your sightseeing on the 28th (Thu) early enough to take a train to Florence.

Things to do in Bologna

Museums · Historic Sites
Find places to stay Oct 27 — 28:

Florence

— 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Castello del Trebbio (in Santa Brigida), Duomo di Siena (in Siena) and Leaning Tower of Pisa (in Pisa). There's much more to do: admire the masterpieces at Florence Academy of Fine Arts, make a trip to Piazzale Michelangelo, appreciate the extensive heritage of Piazza della Signoria, and examine the collection at Pitti Palace.

To find ratings, reviews, and tourist information, you can read our Florence route builder tool.

Getting from Bologna to Florence by train takes about 1.5 hours. Other options: drive; or take a bus. In October, plan for daily highs up to 71°F, and evening lows to 54°F. Wrap up your sightseeing on the 31st (Sun) early enough to take a train to Rome.

Things to do in Florence

Historic Sites · Museums · Wineries

Side Trips

Find places to stay Oct 28 — 31:

Rome

— 4 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, nightlife, and museums. Your trip includes some of its best attractions: take in the architecture and atmosphere at St. Peter's Basilica, explore the ancient world of Palatine Hill, admire the local landmark of Trevi Fountain, and contemplate the long history of Colosseum.

To see maps, ratings, reviews, and more tourist information, use the Rome route planning tool.

You can take a train from Florence to Rome in 2.5 hours. Alternatively, you can fly; or drive. Expect a daytime high around 73°F in October, and nighttime lows around 55°F. Wrap up your sightseeing on the 4th (Thu) to allow time to take a train to Naples.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trip

Find places to stay Oct 31 — Nov 4:

Naples

— 3 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You'll find plenty of places to visit near Naples: Giardino della Minerva (in Salerno), Walk of the Gods (in Positano) and Lupanar (in Pompeii). The adventure continues: delve into the distant past at Pompeii Archaeological Park, admire the striking features of Villa Rufolo, do sightseeing your way with Amalfi Coast Drive, and examine the collection at Museo Archeologico Nazionale di Napoli.

To find traveler tips, photos, and other tourist information, you can read our Naples trip maker.

Traveling by train from Rome to Naples takes 2 hours. Alternatively, you can drive; or fly. Expect a daytime high around 66°F in November, and nighttime lows around 50°F. Wrap up your sightseeing on the 7th (Sun) early enough to fly to Cinque Terre.

Things to do in Naples

Historic Sites · Museums · Parks · Outdoors

Side Trips

Find places to stay Nov 4 — 7:

Cinque Terre

— 3 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Change things up with these side-trips from Cinque Terre: Genoa (Cattedrale di San Lorenzo - Duomo di Genova, Aquarium of Genoa, &more), Parco Naturale Regionale di Porto Venere (in La Spezia) and Hike the Punta Manara (in Sestri Levante). It doesn't end there: discover the deep blue sea with Enjoy Cinqueterre Boat Tours.

To find photos, other places to visit, where to stay, and tourist information, use the Cinque Terre route planning website.

You can fly from Naples to Cinque Terre in 3 hours. Other options are to drive; or take a train. When traveling from Naples in November, plan for slightly colder days in Cinque Terre, with highs around 61°F, while nights are about the same with lows around 46°F. Finish your sightseeing early on the 10th (Wed) so you can drive to Milan.

Things to do in Cinque Terre

Parks · Outdoors · Historic Sites · Museums

Side Trips

Find places to stay Nov 7 — 10:

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.
On the 11th (Thu), admire the striking features of Galleria Vittorio Emanuele II, then take in the architecture and atmosphere at Duomo di Milano, and then stroll the grounds of Monumental Cemetery.

To find reviews and other tourist information, use the Milan day trip planner.

You can drive from Cinque Terre to Milan in 3 hours. Another option is to take a train. When traveling from Cinque Terre in November, plan for a bit cooler days and about the same nights in Milan: temperatures range from 55°F by day to 42°F at night. Finish your sightseeing early on the 11th (Thu) to allow enough time to fly back home.

Things to do in Milan

Historic Sites · Shopping
Find places to stay Nov 10 — 11:

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.