39 days in Italy Itinerary

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.

Kick off your visit on the 28th (Tue): admire the striking features of Galleria Vittorio Emanuele II, then take in the spiritual surroundings of Duomo di Milano, then get engrossed in the history at Basilica di Sant'Ambrogio, and finally explore the historical opulence of Castello Sforzesco.

For where to stay, photos, ratings, and other tourist information, refer to the Milan day trip planning site .

Toronto, Canada to Milan is an approximately 11.5-hour flight. You can also do a combination of flight and train. Due to the time zone difference, you'll lose 6 hours traveling from Toronto to Milan. When traveling from Toronto in May, plan for a bit warmer days in Milan, with highs around 26°C, while nights are about the same with lows around 15°C. Wrap up your sightseeing on the 28th (Tue) to allow time to take a train to Rome.

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.

Let the collections at Vatican Museums and Museo Nazionale di Castel Sant'Angelo capture your imagination. Do some cultural sightseeing at Palatine Hill and St. Peter's Basilica. You'll find plenty of places to visit near Rome: Tivoli (Villa Adriana & Villa d'Este). The adventure continues: explore the ancient world of Colosseum, admire the masterpieces at Galleria Borghese, take a stroll through Trastevere, and make a trip to Pantheon.

To find ratings, reviews, more things to do, and other tourist information, you can read our Rome trip itinerary planner.

Traveling by train from Milan to Rome takes 3 hours. Alternatively, you can fly; or drive. In May, daytime highs in Rome are 28°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 3rd (Mon) to allow time to take a train to Naples.

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Visit Gli Scavi Archeologici di Pompei and Museo Cappella Sansevero for their historical value. Shop till you drop at Archivio Fotografico Parisio and I Presepi da Guinness. There's still lots to do: brush up on your military savvy at Galleria Borbonica, engage your brain at MUSA - Museo Universitario delle Scienze e delle Arti, explore the ancient world of Parco Archeologico Pausilypon, and contemplate the long history of Catacombe di San Gaudioso.

For traveler tips, where to stay, other places to visit, and tourist information, use the Naples trip planning app .

You can take a train from Rome to Naples in 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 32°C in June, and nighttime lows around 22°C. Finish up your sightseeing early on the 8th (Sat) so you can go by car to Positano.

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.

Get some cultural insight at Sol’Art Ceramiche and Ceramiche D'Arte Pascal. Your inner history buff will appreciate Duomo di Ravello and Cappella Sant'Angelo all'Ospedale. Explore the numerous day-trip ideas around Positano: Vietri sul Mare (Le Vigne di Raito & Parrocchia San Giovanni), Castiglione (Spiaggia di castiglione & Lido di Ravello) and Ravello (Ceramiche d'Arte Carmela & Villa Cimbrone Gardens). The adventure continues: kick back and relax at Fornillo, stroll through Lido Capo di Conca, soothe aching muscles at Otium Spa Costa d'Amalfi, and take in the spiritual surroundings of Duomo di Sant'Andrea.

For more things to do, reviews, photos, and tourist information, read Positano attractions planner.

Drive from Naples to Positano in 1.5 hours. Alternatively, you can take a bus; or do a combination of subway and bus. In June, daily temperatures in Positano can reach 32°C, while at night they dip to 23°C. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Assisi.

Rich in culture and religious tradition, Assisi is known as the birthplace of St.

Museum-lovers will get to explore Museo della Porziuncola and Museo del Pianoforte Storico e del Suono. Shop till you drop at B.A.T. Assisi and Gambacorta Bottega del Buongustaio. Get out of town with these interesting Assisi side-trips: Montioni Frantoio e Cantina (in Montefalco), Azienda Agraria Guerrieri (in Piagge) and Vineria del Carmine (in La Bruna). There's much more to do: pause for some serene contemplation at Basilica inferiore di San Francesco d'Assisi, contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli - Porziuncola, steep yourself in history at Basilica di Santa Chiara, and make a trip to Eremo delle Carceri.

To find where to stay, photos, traveler tips, and other tourist information, use the Assisi trip itinerary maker app .

You can drive from Positano to Assisi in 5 hours. Alternatively, you can do a combination of bus, subway, and train; or take a bus. Plan for slightly colder nights when traveling from Positano in June since evenings lows in Assisi dip to 18°C. Cap off your sightseeing on the 18th (Tue) early enough to go by car to Florence.

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.

Get some cultural insight at Galleria dell'Accademia and Cathedral of Santa Maria del Fiore. The Baptistery of St. John and Campanile di Giotto will appeal to history buffs. Explore the numerous day-trip ideas around Florence: Siena Cathedral (in Siena), Guardastelle Vineyard (in San Gimignano) and Castello del Trebbio (in Santa Brigida). The adventure continues: explore the world behind art at Uffizi Galleries, get engrossed in the history at Basilica di Santa Croce, ponder the world of politics at Museo Nazionale del Bargello, and get to know the fascinating history of Piazza della Signoria.

For traveler tips, other places to visit, reviews, and other tourist information, refer to the Florence journey website .

Drive from Assisi to Florence in 2.5 hours. Alternatively, you can take a train. In June in Florence, expect temperatures between 33°C during the day and 21°C at night. Wrap up your sightseeing on the 23rd (Sun) to allow time to take a train to Verona.

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.

Deepen your sense of the past at sights like Arena di Verona and Basilica di San Zeno Maggiore. For shopping fun, head to Piazza delle Erbe or Libreria Antiquaria Perini. There's lots more to do: wander the streets of Quinzano, do a tasting at Villa Mosconi Bertani, take in the architecture and atmosphere at Chiesa di San Fermo, and admire the striking features of Casa di Giulietta.

For where to stay, ratings, photos, and tourist information, use the Verona day trip planner.

Traveling by train from Florence to Verona takes 2 hours. Alternatively, you can drive; or take a bus. In June, daily temperatures in Verona can reach 34°C, while at night they dip to 20°C. Finish up your sightseeing early on the 28th (Fri) so you can catch the train to Venice.

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.

For shopping fun, head to Galleria S.Eufemia or Il Forcolaio Matto. Deepen your sense of the past at sights like Basilica di San Marco and Doge's Palace. Change things up with these side-trips from Venice: Padua (Scrovegni Chapel, Chiesa degli Eremitani, & more). There's still lots to do: get to know the fascinating history of St. Mark's Square, take in the spiritual surroundings of Campo del Ghetto, explore the world behind art at Peggy Guggenheim Collection, and pause for some serene contemplation at San Giorgio Maggiore.

To see traveler tips, where to stay, and tourist information, go to the Venice day trip planning tool .

Take a train from Verona to Venice in 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 32°C in June, and nighttime lows around 20°C. Finish your sightseeing early on the 4th (Thu) so you can travel back home.