18 days in Italy Itinerary

18 days in Italy Itinerary

Created using Inspirock Italy trip planner

Make it your trip
Fly
1
Milan
— 1 night
Train
2
Florence
— 3 nights
Drive
3
Siena
— 3 nights
Drive
4
Rome
— 3 nights
Train
5
Pompeii
— 1 night
Drive
6
Positano
— 3 nights
Fly
7
Venice
— 3 nights
Fly

S M T W T F S
29
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31
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5
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18

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 2nd (Thu), don't miss a visit to Galleria Vittorio Emanuele II, then contemplate in the serene atmosphere at Duomo di Milano, then examine the collection at Civic Archaeological Museum, and finally get engrossed in the history at Pinacoteca Ambrosiana.

To find where to stay, reviews, and tourist information, you can read our Milan road trip app.

Montreal, Canada to Milan is an approximately 13.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. September in Milan sees daily highs of 28°C and lows of 16°C at night. Wrap up your sightseeing on the 2nd (Thu) to allow time to take a train to Florence.

Things to do in Milan

Museums · Historic Sites · Shopping
Find places to stay Sep 1 — 2:

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.
Florence is known for museums, historic sites, and shopping. Your trip includes some of its best attractions: admire the masterpieces at Florence Academy of Fine Arts, pause for some serene contemplation at Basilica of Santa Croce, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and admire the natural beauty at The Boboli Gardens.

For photos, traveler tips, more things to do, and more tourist information, you can read our Florence journey planner.

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. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Siena.

Things to do in Florence

Historic Sites · Museums · Tours · Parks
Find places to stay Sep 2 — 5:

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.
Change things up with these side-trips from Siena: San Gimignano (Guardastelle Vineyard, Podere La Marronaia- Sosta Alle Colonne, &more). There's lots more to do: gain insight at Scuola di Cucina di Lella, don't miss a visit to Piazza del Campo, take in the spiritual surroundings of San Francesco, and awaken your taste buds at some of the top wineries in the area.

To see traveler tips, where to stay, more things to do, and more tourist information, read Siena visit planner.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. September in Siena sees daily highs of 32°C and lows of 19°C at night. Wrap up your sightseeing on the 8th (Wed) to allow time to drive to Rome.

Things to do in Siena

Wineries · Historic Sites · Tours · Museums

Side Trip

Find places to stay Sep 5 — 8:

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, nightlife, and museums. Your trip includes some of its best attractions: take in the architecture and atmosphere at St. Peter's Basilica, make a trip to Trevi Fountain, explore the ancient world of Colosseum, and admire the landmark architecture of Pantheon.

To see photos, more things to do, maps, and other tourist information, you can read our Rome journey website.

Traveling by car from Siena to Rome takes 2.5 hours. Alternatively, you can take a bus; or take a train. In September, daytime highs in Rome are 32°C, while nighttime lows are 18°C. Wrap up your sightseeing on the 11th (Sat) to allow time to take a train to Pompeii.

Things to do in Rome

Historic Sites · Museums · Neighborhoods

Side Trip

Find places to stay Sep 8 — 11:

Pompeii

— 1 night

Underground City

Pompeii has been a tourist destination for more than 250 years.
On the 12th (Sun), admire the striking features of Villa dei Misteri, explore the ancient world of House of Menander (Casa del Menandro), then learn about winemaking at Bosco de Medici Winery, and finally delve into the distant past at Pompeii Archaeological Park.

To find other places to visit, reviews, ratings, and other tourist information, refer to the Pompeii road trip planning tool.

You can take a train from Rome to Pompeii in 2.5 hours. Other options are to drive; or take a bus. In September in Pompeii, expect temperatures between 31°C during the day and 20°C at night. Finish your sightseeing early on the 12th (Sun) so you can drive to Positano.

Things to do in Pompeii

Historic Sites · Wineries
Find places to stay Sep 11 — 12:

Positano

— 3 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.
Venture out of the city with trips to Amalfi (Antichi Sapori d'Amalfi, Duomo di Sant'Andrea, &more) and Ravello (Villa Cimbrone Gardens, Villa Rufolo, &more). And it doesn't end there: get a new perspective on things with Boat Tours & Water Sports, get great views at Il Sentiero Degli Dei, enjoy the sand and surf at Fornillo, and enjoy breathtaking views from Torre di Grado.

To see other places to visit, ratings, photos, and more tourist information, use the Positano online sightseeing planner.

Getting from Pompeii to Positano by car takes about 1.5 hours. Other options: take a bus. In September in Positano, expect temperatures between 31°C during the day and 23°C at night. Finish up your sightseeing early on the 15th (Wed) so you can catch the flight to Venice.

Things to do in Positano

Outdoors · Historic Sites · Parks · Tours

Side Trips

Find places to stay Sep 12 — 15:

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.
When in Venice, make a side trip to see Basilica of St. Anthony in Padua, approximately Padua away. Next up on the itinerary: contemplate the waterfront views at Canal Grande, savor the flavors at Food & Drink, take in the views from Ponte dei Sospiri, and take in the architecture and atmosphere at Basilica di San Marco.

For traveler tips, ratings, other places to visit, and other tourist information, read Venice trip planning app.

Getting from Positano to Venice by flight takes about 3 hours. Other options: drive; or do a combination of bus and train. Expect little chillier evenings in Venice when traveling from Positano in September, with lows around 17°C. Finish your sightseeing early on the 18th (Sat) so you can fly back home.

Things to do in Venice

Historic Sites · Museums · Tours · Nature

Side Trip

Find places to stay Sep 15 — 18:

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.