32 days in Italy Itinerary

32 days in Italy Itinerary

Created using Inspirock Italy trip planner

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

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Milan

— 5 nights

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.
La Libreria Del Mare has been added to your itinerary. Family-friendly places like Duomo di Milano and Castello Sforzesco will thrill your kids. Change things up with these side-trips from Milan: La Citta Alta (in Bergamo), Tremezzina (Villa del Balbianello & Villa Carlotta) and Leolandia (in Capriate San Gervasio). The adventure continues: admire the striking features of Galleria Vittorio Emanuele II, examine the collection at Museo Della Scienza E Della Tecnologia Leonardo da Vinci, explore the different monuments and memorials at Monumental Cemetery, and contemplate in the serene atmosphere at Il Cenacolo.

To find where to stay, photos, traveler tips, and more tourist information, refer to the Milan trip planning website.

Montreal, Canada to Milan is an approximately 13.5-hour flight. Due to the time zone difference, you'll lose 6 hours traveling from Montreal to Milan. In May, daily temperatures in Milan can reach 26°C, while at night they dip to 15°C. Wrap up your sightseeing on the 6th (Fri) early enough to drive to Verona.

Things to do in Milan

Historic Sites · Museums · Shopping · Theme Parks

Side Trips

Find places to stay May 1 — 6:

Verona

— 5 nights

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.
Kids will appreciate attractions like Gardaland Park and Lago di Garda. Explore the numerous day-trip ideas around Verona: Basilica di Sant'Andrea di Mantova (in Mantua), Gardaland SEA LIFE Aquarium (in Castelnuovo del Garda) and Parco Giardino Sigurta (in Valeggio Sul Mincio). Next up on the itinerary: experience the emotional art of opera at Arena di Verona, admire the landmark architecture of Casa di Giulietta, contemplate in the serene atmosphere at Basilica di San Zeno Maggiore, and soak in style at Spa Termale Aquaria.

To find more things to do, other places to visit, traveler tips, and other tourist information, read our Verona day trip planning app.

Traveling by car from Milan to Verona takes 2 hours. Alternatively, you can take a train. Expect a daytime high around 27°C in May, and nighttime lows around 13°C. Finish your sightseeing early on the 11th (Wed) to allow enough time to take a train to Florence.

Things to do in Verona

Parks · Theme Parks · Historic Sites · Zoos & Aquariums

Side Trips

Find places to stay May 6 — 11:

Florence

— 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Attractions like Florence Academy of Fine Arts and Ponte Vecchio make great kid-friendly stops. Change things up with these side-trips from Florence: Pisa (Leaning Tower of Pisa & Museo Aviotruppe Esercito Italiano) and San Michele in Foro (in Lucca). There's lots more to do: don't miss a visit to Piazzale Michelangelo, admire the striking features of The Baptistery of St. John, ponder the world of politics at Palazzo Vecchio, and get to know the fascinating history of Piazza del Duomo.

For more things to do, other places to visit, reviews, and other tourist information, you can read our Florence trip itinerary builder tool.

Getting from Verona to Florence by train takes about 2.5 hours. Other options: drive. May in Florence sees daily highs of 25°C and lows of 13°C at night. Finish up your sightseeing early on the 16th (Mon) so you can catch the train to Rome.

Things to do in Florence

Historic Sites · Museums · Tours · Parks

Side Trips

Find places to stay May 11 — 16:

Rome

— 5 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Kids will appreciate attractions like Colosseum and Palatine Hill. There's much more to do: explore the ancient world of Pantheon, admire the masterpieces at Galleria Borghese, don't miss a visit to Spanish Steps, and get engrossed in the history at Musei Capitolini.

For more things to do, reviews, other places to visit, and more tourist information, read Rome trip planner.

Traveling by train from Florence to Rome takes 2.5 hours. Alternatively, you can fly; or drive. Plan for somewhat warmer nights when traveling from Florence in May since evenings lows in Rome dip to 17°C. Wrap up your sightseeing on the 21st (Sat) early enough to drive to Positano.

Things to do in Rome

Historic Sites · Museums · Tours · Neighborhoods

Side Trip

Find places to stay May 16 — 21:

Positano

— 5 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.
Fornillo has been added to your itinerary. Bring the kids along to Villa Cimbrone Gardens and Il Sentiero Degli Dei. Get out of town with these interesting Positano side-trips: Ravello (Ceramiche Cosmolena di Margherita di Palma, Villa Rufolo, &more), Amalfi (Museo della Carta, Cloister del Paradiso, &more) and Sorrento (St Francis Church and Convent, Piazza Tasso, &more). Next up on the itinerary: take a memorable drive along Amalfi Coast, head outdoors with Walk of the Gods, take a tour by water with Boat Tours & Water Sports, and take in the spiritual surroundings of Church of Santa Maria Assunta.

For other places to visit, photos, maps, and tourist information, refer to the Positano trip planning website.

Getting from Rome to Positano by car takes about 3.5 hours. Other options: do a combination of train and bus; or take a bus. May in Positano sees daily highs of 27°C and lows of 18°C at night. Cap off your sightseeing on the 26th (Thu) early enough to catch the flight to Venice.

Things to do in Positano

Outdoors · Parks · Historic Sites · Beaches

Side Trips

Find places to stay May 21 — 26:

Venice

— 5 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.
Attractions like Canal Grande and Basilica di San Marco make great kid-friendly stops. Explore Venice's surroundings by going to Padua (Chiesa degli Eremitani - World Heritage Site, Basilica of St. Anthony, &more). There's much more to do: admire the striking features of Doge's Palace, take in the views from Ponte di Rialto, explore the galleries of Peggy Guggenheim Collection, and get the lay of the land with Walking tours.

To see ratings, reviews, photos, and tourist information, read our Venice vacation maker app.

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 May, expect slightly colder with lows of 15°C in Venice. Finish your sightseeing early on the 31st (Tue) to allow enough time to fly back home.

Things to do in Venice

Historic Sites · Museums · Parks · Tours

Side Trip

Find places to stay May 26 — 31:

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.