22 days in Italy Itinerary

Created using Inspirock Italy vacation planner
Make it your trip
Fly
1
Milan
— 1 night
Train
2
Florence
— 3 nights
Drive
3
Siena
— 3 nights
Drive
4
Assisi
— 2 nights
Drive
5
Rome
— 4 nights
Drive
6
Positano
— 4 nights
Fly
7
Venice
— 4 nights
Fly

S M T W T F S
27
28
29
30
31
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2
3
4
5
6
7
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9
10
11
12
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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.
Start off your visit on the 2nd (Sat): sample some tasty brews at a beer tour and tasting, contemplate in the serene atmosphere at Chiesa di San Cristoforo sul Naviglio, get a new perspective on things with Boat Tours & Water Sports, then admire the masterpieces at Museum of Decorative Arts, and finally explore the world behind art at Museum of Ancient Art.

For other places to visit, where to stay, more things to do, and tourist information, refer to the Milan road trip website.

Ottawa, Canada to Milan is an approximately 14-hour flight. Traveling from Ottawa to Milan, you'll lose 6 hours due to the time zone difference. Traveling from Ottawa in September, Milan is a bit warmer at night with lows of 16°C. Finish up your sightseeing early on the 2nd (Sat) so you can catch the train to Florence.
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Museums · Tours · Wineries · Historic Sites

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.
Get a sense of the local culture at Corridoio Vasariano and Mus.e Firenze Palazzo Vecchio. Discover out-of-the-way places like Fountain of Neptune and Castello di Montefioralle. Venture out of the city with trips to Greve in Chianti (Piazza Matteotti, Enoteca Falorni, &more). The adventure continues: tour the pleasant surroundings at Giardino Bardini, see the interesting displays at Convento di San Francesco, take in the architecture and atmosphere at Basilica di San Lorenzo, and contemplate in the serene atmosphere at Holy Trinity.

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

You can take a train from Milan to Florence in 2.5 hours. Other options are to drive; or take a bus. September in Florence sees daily highs of 30°C and lows of 17°C at night. Finish your sightseeing early on the 5th (Tue) so you can drive to Siena.
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Museums · Historic Sites · Wineries · Neighborhoods
Side Trips

Siena — 3 nights

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Get a sense of the local culture at Azienda Agricola La Lastra and Fattoria San Donato. You'll discover tucked-away gems like Truffle Hunting in Tuscany and Cappella di Piazza. Venture out of the city with trips to Montepulciano (Bottega del Rame, Via di Gracciano nel Corso, &more) and San Gimignano (Mura di San Gimignano, Balducci Ceramica, &more). There's still lots to do: see the interesting displays at Museo dell'Acqua, pause for some serene contemplation at Basilica di San Clemente in Santa Maria dei Servi, make a trip to Via di Citta, and admire the landmark architecture of Palazzo Sansedoni.

Use Inspirock's suggestions to plan your Siena trip and find the best activities and attractions for your vacation.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Finish your sightseeing early on the 8th (Fri) to allow enough time to drive to Assisi.
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Historic Sites · Museums · Shopping · Wineries
Side Trips

Assisi — 2 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 9th (Sat): relax and rejuvenate at Nun Spa Museum, take in the architecture and atmosphere at St. Peter's Abbey, then take in the spiritual surroundings of Cripta di San Francesco, then pause for some serene contemplation at Chiesa Santo Stefano, and finally take in the spiritual surroundings of Oratorio dei Pellegrini. Keep things going the next day: pause for some serene contemplation at Saint Andrea, see the interesting displays at Villa dei Mosaici, contemplate the long history of Borgo Antico di Colle Pino, then explore the ancient world of Parrocchia Santa Maria Maggiore - Frati Cappuccini Assisi, and finally view the masterpieces at Chiesa di Santa Maria delle Rose. Mostra Maria.

For ratings, maps, traveler tips, and more tourist information, use the Assisi trip itinerary builder app.

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. In September, plan for daily highs up to 30°C, and evening lows to 16°C. Wrap up your sightseeing on the 10th (Sun) to allow time to drive to Rome.
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Historic Sites · Museums · Spas · Shopping
Side Trip

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.
Take a break from the city and head to Colle Aventino and Lido Ganimede. You'll explore the less-touristy side of things at Necropoli della Banditaccia and Villa Di Tiberio. Venture out of the city with trips to Bau Beach (in Maccarese), Bunker Soratte (in Sant'Oreste) and Cerite National Museum (in Cerveteri). Next up on the itinerary: appreciate the history behind Trajan's Column, take in nature's colorful creations at Monte Pincio, glide through the air with a parasailing or paragliding tour, and pause for some serene contemplation at Basilica dei SS. Ambrogio e Carlo al Corso.

For ratings, maps, and tourist information, read our Rome online route planner.

You can drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. In September in Rome, expect temperatures between 32°C during the day and 18°C at night. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Positano.
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Historic Sites · Parks · Outdoors · Beaches
Side Trips

Positano — 4 nights

Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
Eschew the tourist crowds and head to Marina di Praia Beach and Duomo dei San Filippo e Giacomo. We've included these beaches for you: Marina of Lobra and Lido di Ravello. Change things up with these side-trips from Positano: Valle dei Mulini (in Amalfi), Sorrento (Gallery Raffaele Celentano, Limonoro, &more) and Chiesa di San Prisco e Agnello (in Sant'Agnello). The adventure continues: contemplate in the serene atmosphere at Basilica della SS. Trinita, look for all kinds of wild species at Le Ali nel Vento - Birds of Prey Experience, make a trip to Parrocchia Di San Gennaro, and take an in-depth tour of MAR - Museo Archeologico Romano Positano.

To find other places to visit, where to stay, reviews, and tourist information, read Positano online journey builder.

Drive from Rome to Positano in 3.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. Traveling from Rome in September, expect somewhat warmer with lows of 23°C in Positano. Wrap up your sightseeing on the 18th (Mon) early enough to fly to Venice.
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Outdoors · Parks · Beaches · Museums
Side Trips

Venice — 4 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.
You'll discover tucked-away gems like Venetian Arsenal and Creature di Gomma - Venice Vintage Toys. Get some cultural insight at Church of San Pantalon and Chiesa di San Giorgio dei Greci. Next up on the itinerary: take in the spiritual surroundings of Chiesa di San Salvador, take a tour by water with Like a Venetian, pause for some serene contemplation at Chiesa di San Zulian (Giuliano), and make a trip to Chiesa di Santa Maria del Giglio (Zobenigo).

To find maps, traveler tips, where to stay, and other tourist information, read Venice journey planner.

Getting from Positano to Venice by flight takes about 3 hours. Other options: drive; or do a combination of bus and train. Traveling from Positano in September, expect little chillier with lows of 17°C in Venice. Wrap up your sightseeing on the 22nd (Fri) to allow time to fly back home.
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Historic Sites · Museums · Neighborhoods · Tours

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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