26 days in Italy Itinerary

Created using Klarna Trips Italy trip builder
Make it your trip
1
Venice
— 1 night
Drive
2
Verona
— 1 night
Train
3
Bologna
— 1 night
Drive
4
Parma
— 1 night
Train
5
Bellagio
— 1 night
Drive
6
Arona
Drive
7
Alba
— 3 nights
Drive
8
Finale Ligure
— 1 night
Drive
9
Genoa
— 1 night
Foot to Recco, Train to Portofino
10
Portofino
Train
11
Cinque Terre
Drive
12
Porto Venere
Drive
13
Viareggio
— 1 night
Drive
14
Livorno
— 1 night
Shuttle
15
Florence
Drive
16
San Gimignano
— 1 night
Drive
17
Monteriggioni
— 1 night
Drive
18
Arezzo
— 2 nights
Drive
19
Montalcino
— 2 nights
Drive
20
Montepulciano
— 4 nights
Drive
21
Rome
— 3 nights

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Venice — 1 night

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 30th (Sat): see the interesting displays at Doge's Palace, then appreciate the extensive heritage of Piazza San Marco, then make a trip to Basilica di San Marco, and finally explore the activities along Canal Grande.

To see maps, ratings, photos, and more tourist information, refer to the Venice online trip itinerary builder.

If you are flying in from Canada, the closest major aiports are Venice Marco Polo Airport, Treviso-Sant'Angelo Airport and Trieste–Friuli Venezia Giulia Airport. September in Venice sees daily highs of 29°C and lows of 17°C at night. Finish your sightseeing early on the 1st (Sun) so you can drive to Verona.
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Historic Sites · Museums · Parks · Nature
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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 1st (Sun), don't miss a visit to Piazza Bra, step into the grandiose world of Museo di Castelvecchio, take in the architecture and atmosphere at Basilica di San Zeno Maggiore, examine the collection at Casa di Giulietta, then take a stroll through Piazza delle Erbe, and finally take in panoramic vistas at Torre dei Lamberti.

To find traveler tips, more things to do, reviews, and other tourist information, read Verona trip itinerary maker.

You can drive from Venice to Verona in 1.5 hours. Other options are to take a shuttle; or take a train. In October in Verona, expect temperatures between 22°C during the day and 11°C at night. Finish up your sightseeing early on the 2nd (Mon) so you can catch the train to Bologna.
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Historic Sites · Shopping · Neighborhoods · Museums
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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.
Kick off your visit on the 2nd (Mon): take in the architecture and atmosphere at Chiesa di San Giacomo Maggiore, take in the architecture and atmosphere at Basilica - Santuario di Santo Stefano, steep yourself in history at Basilica di San Petronio, then take an in-depth tour of Museo Civico Archeologico, then make a trip to Piazza Maggiore, and finally enjoy breathtaking views from Le Due Torri Torre degli Asinell.

To find other places to visit, traveler tips, photos, and more tourist information, you can read our Bologna trip itinerary maker website.

Getting from Verona to Bologna by train takes about 1.5 hours. Other options: drive; or take a bus. In October, daytime highs in Bologna are 22°C, while nighttime lows are 13°C. Finish your sightseeing early on the 3rd (Tue) so you can drive to Parma.
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Parma — 1 night

Capital of Italian Food Valley

Parma is famous for its prosciutto, cheese, and architecture.
Start off your visit on the 3rd (Tue): contemplate in the serene atmosphere at Battistero di Parma, walk around Parco Ducale, then savor the flavors at Food & Drink, and finally contemplate in the serene atmosphere at Cattedrale di Parma.

For other places to visit, more things to do, where to stay, and other tourist information, read Parma travel route planning tool.

You can drive from Bologna to Parma in 1.5 hours. Other options are to take a train; or take a shuttle. In October, daily temperatures in Parma can reach 21°C, while at night they dip to 12°C. Wrap up your sightseeing on the 4th (Wed) early enough to take a train to Bellagio.
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Tours · Parks · Historic Sites
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Bellagio — 1 night

Pearl of Lake Como

Known as the pearl of Lake Como for its luxury accommodations, high-end shops, and fine dining options, Bellagio serves as the lake's premiere resort town.
On the 4th (Wed), pause for some serene contemplation at Chiesa di S. Leonardo, take in the architecture and atmosphere at Basilica di San Giacomo, look for gifts at Azalea - Silk of Como, then paddle through the water with a kayaking and canoeing tour, then take in nature's colorful creations at I Giardini di Villa Melzi, and finally walk around La Punta Spartivento.

To find ratings, photos, reviews, and other tourist information, read our Bellagio trip planner.

Getting from Parma to Bellagio by train takes about 2.5 hours. Other options: drive; or take a bus. In October, daily temperatures in Bellagio can reach 20°C, while at night they dip to 11°C. Finish up your sightseeing early on the 5th (Thu) so you can go by car to Arona.
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Parks · Adventure · Outdoors · Tours
Side Trip
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Arona

Arona is a town and comune on Lake Maggiore, in the province of Novara (northern Italy). To find other places to visit, ratings, reviews, and more tourist information, refer to the Arona day trip planning app.

Traveling by car from Bellagio to Arona takes 2 hours. Alternatively, you can take a train; or do a combination of bus and train. Expect a daytime high around 21°C in October, and nighttime lows around 9°C. On the 5th (Thu), you'll travel to Alba.
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Historic Sites · Nightlife · Parks · Outdoors
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Alba — 3 nights

Alba is a town and comune of Piedmont, Italy, in the province of Cuneo. Alba is known for sightseeing, historic sites, and wineries. Your trip includes some of its best attractions: admire the verdant scenery at Langhe landscapes, learn about winemaking at Ceretto Aziende Vitivinicole, examine the collection at WiMu - Museo del Vino a Barolo, and indulge your senses at Travel Langhe Wine Tours.

To find ratings, where to stay, reviews, and tourist information, read Alba driving holiday website.

Drive from Arona to Alba in 2 hours. Alternatively, you can take a train; or take a bus. In October, daytime highs in Alba are 20°C, while nighttime lows are 9°C. Cap off your sightseeing on the 8th (Sun) early enough to go by car to Finale Ligure.
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Wineries · Parks · Nature · Historic Sites
Side Trips
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Finale Ligure — 1 night

Finale Ligure is a comune on the Gulf of Genoa in the Province of Savona in Liguria, Italy. On the 8th (Sun), don't miss a visit to Finalborgo, kick back and relax at Bagni Garibaldi, then Head underground at Grotte di Toirano, and finally enjoy the sand and surf at Varigotti Beach.

For where to stay, reviews, other places to visit, and more tourist information, refer to the Finale Ligure trip planner.

You can drive from Alba to Finale Ligure in 2 hours. Other options are to take a bus; or take a train. Traveling from Alba in October, expect Finale Ligure to be somewhat warmer, temps between 24°C and 14°C. Wrap up your sightseeing on the 9th (Mon) to allow time to drive to Genoa.
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Parks · Beaches · Outdoors · Nature
Side Trip
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Genoa — 1 night

Once the most important harbor in the Mediterranean Sea, Genoa has a long history as a rich and powerful trade center in northern Italy.
Kick off your visit on the 9th (Mon): contemplate in the serene atmosphere at Cattedrale di San Lorenzo - Duomo di Genova, then observe the fascinating underwater world at Aquarium of Genoa, then take a leisurely stroll along Old Port, and finally visit Boccadasse.

To see more things to do, maps, traveler tips, and other tourist information, read Genoa itinerary planning site.

Drive from Finale Ligure to Genoa in 1.5 hours. Alternatively, you can take a train; or take a bus. October in Genoa sees daily highs of 24°C and lows of 17°C at night. Finish up your sightseeing early on the 10th (Tue) so you can travel to Portofino.
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Neighborhoods · Parks · Zoos & Aquariums · Historic Sites
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Portofino

Portofino is an Italian fishing village and holiday resort famous for its picturesque harbour and historical association with celebrity and artistic visitors. On the 10th (Tue), identify plant and animal life at Area Marina Protetta Portofino, then enjoy the sea views from Faro Di Portofino, and then step into the grandiose world of Castello Brown.

To find more things to do, ratings, traveler tips, and other tourist information, read our Portofino trip planner.

Getting from Genoa to Portofino by train takes about an hour. Other options: drive; or take a train. In October, daily temperatures in Portofino can reach 24°C, while at night they dip to 17°C. Wrap up your sightseeing on the 10th (Tue) to allow time to take a train to Cinque Terre.
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Historic Sites · Wildlife · Parks
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Cinque Terre

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
On the 10th (Tue), get great views at View Point Corniglia.

To see more things to do and other tourist information, read Cinque Terre trip itinerary planner.

Take a train from Portofino to Cinque Terre in 1.5 hours. Alternatively, you can drive. Traveling from Portofino in October, expect little chillier with lows of 14°C in Cinque Terre. Wrap up your sightseeing on the 10th (Tue) to allow time to drive to Porto Venere.
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Highlights from your trip

Porto Venere

Porto Venere is a town and comune (municipality) located on the Ligurian coast of Italy in the province of La Spezia. To see ratings, photos, and tourist information, go to the Porto Venere trip planner.

Traveling by car from Cinque Terre to Porto Venere takes 1.5 hours. Alternatively, you can ride a ferry. October in Porto Venere sees daily highs of 25°C and lows of 14°C at night. You'll set off for Viareggio on the 10th (Tue).
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Outdoors · Parks · Nature · Tours
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Viareggio — 1 night

Viareggio is a city and comune in northern Tuscany, Italy, on the coast of the Tyrrhenian Sea. On the 11th (Wed), tour the pleasant surroundings at Bagno Irene, don't miss a visit to Villa Argentina, then don't miss a visit to La Passeggiata, and finally see the interesting displays at Museo Villa Puccini.

To see other places to visit, more things to do, ratings, and tourist information, you can read our Viareggio road trip app.

Drive from Porto Venere to Viareggio in 1.5 hours. Alternatively, you can do a combination of bus and train. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Wrap up your sightseeing on the 11th (Wed) early enough to drive to Livorno.
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Beaches · Outdoors · Parks · Museums
Side Trip
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Livorno — 1 night

Naples of the North

Considered one of Tuscany's newer cities, the busy port city of Livorno boasts modern charm uncharacteristic of the region.
For where to stay, photos, more things to do, and tourist information, go to the Livorno trip itinerary builder.

You can drive from Viareggio to Livorno in an hour. Another option is to take a train. In October, daytime highs in Livorno are 25°C, while nighttime lows are 14°C. On the 12th (Thu), you'll travel to Florence.
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Outdoors · Parks · Historic Sites · Tours
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Florence

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Plan a Florence trip in moments using our itinerary builder.

You can take a shuttle from Livorno to Florence in 1.5 hours. Alternatively, you can drive; or take a train. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. On the 12th (Thu), you'll travel to San Gimignano.
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Tours · Historic Sites · Shopping · Wineries
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San Gimignano — 1 night

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
On the 12th (Thu), learn about winemaking at Guardastelle Vineyard, take in the architecture and atmosphere at Duomo di San Gimignano, then contemplate the long history of Historic Centre of San Gimignano, and finally make a trip to San Gimignano Bell Tower.

For traveler tips, more things to do, ratings, and more tourist information, you can read our San Gimignano trip itinerary planner.

You can drive from Florence to San Gimignano in 1.5 hours. Other options are to take a train; or take a bus. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. Finish up your sightseeing early on the 13th (Fri) so you can go by car to Monteriggioni.
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Wineries · Historic Sites
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Monteriggioni — 1 night

Start off your visit on the 13th (Fri): contemplate in the serene atmosphere at Chiesa di Santa Maria Assunta, step into the grandiose world of Castello di Monteriggioni, admire the striking features of Walls of Monteriggioni, then see the interesting displays at Museo Delle Armature, then appreciate the extensive heritage of Centro storico di Monteriggioni, and finally do a tasting at Sant'Agnese Farm.

To find ratings, reviews, other places to visit, and tourist information, go to the Monteriggioni trip planner.

You can drive from San Gimignano to Monteriggioni in an hour. Alternatively, you can take a bus. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Finish up your sightseeing early on the 14th (Sat) so you can go by car to Arezzo.
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Historic Sites · Wineries · Museums
Side Trips
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Arezzo — 2 nights

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Start off your visit on the 14th (Sat): steep yourself in history at Museo Casa di Giorgio Vasari, take in the architecture and atmosphere at San Domenico Church, take in the architecture and atmosphere at Arezzo Cathedral, take in the spiritual surroundings of San Francesco, Arezzo, then don't miss a visit to Piazza Grande, and finally contemplate in the serene atmosphere at Santa Maria della Pieve. Keep things going the next day: contemplate in the serene atmosphere at Eremo di Camaldoli, then explore the historical opulence of Castello di Poppi dei Conti Guidi, then examine the collection at Anghiari, and finally appreciate the history behind La Madonna di Citerna di Donatello.

To find out how to plan a trip to Arezzo, use our trip itinerary maker.

Traveling by car from Monteriggioni to Arezzo takes 1.5 hours. Alternatively, you can take a bus; or take a train. Cap off your sightseeing on the 16th (Mon) early enough to go by car to Montalcino.
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Side Trips
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Montalcino — 2 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 16th (Mon), take in panoramic vistas at Fortezza di Montalcino, then learn about winemaking at il Cocco, then learn about winemaking at Ciacci Piccolomini d'Aragona, and finally pause for some serene contemplation at Abbazia di Sant'Antimo. On your second day here, contemplate the long history of San Quirico d'Orcia, contemplate the long history of Terme Bagno Vignoni, then contemplate in the serene atmosphere at Abbazia di Monte Oliveto Maggiore, and finally do a tasting at Winery Solaria Patrizia Cencioni.

For more things to do, traveler tips, and tourist information, read Montalcino travel route planner.

Drive from Arezzo to Montalcino in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Finish your sightseeing early on the 18th (Wed) to allow enough time to drive to Montepulciano.
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Historic Sites · Wineries · Shopping
Side Trips
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Montepulciano — 4 nights

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Change things up with these side-trips from Montepulciano: Orvieto (Pozzo di San Patrizio, Duomo di Orvieto, &more), Civita di Bagnoregio (in Bagnoregio) and Cortona (Piazza della Repubblica, Museo Diocesano, &more). There's much more to do: do a tasting at Icario Winery, contemplate in the serene atmosphere at Tempio di San Biagio, make a trip to Piazza Grande a Montepulciano, and view the masterpieces at Quinteaquadri Lab Gallery.

To see more things to do, reviews, maps, and other tourist information, read our Montepulciano online route maker.

Getting from Montalcino to Montepulciano by car takes about an hour. Other options: take a bus. In October, daytime highs in Montepulciano are 26°C, while nighttime lows are 15°C. Finish up your sightseeing early on the 22nd (Sun) so you can go by car to Rome.
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Wineries · Historic Sites · Museums · Spas
Side Trips
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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: make a trip to St. Peter's Basilica, steep yourself in history at Roman Forum, admire the landmark architecture of Pantheon, and admire the masterpieces at Galleria Borghese.

To find other places to visit, traveler tips, maps, and other tourist information, refer to the Rome online tour builder.

You can drive from Montepulciano to Rome in 2 hours. Other options are to take a train; or take a bus. In October in Rome, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 25th (Wed) so you can travel back home.
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Side Trip
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Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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