39 days in Italy Itinerary

39 days in Italy Itinerary

Created using Inspirock Italy holiday planner

This plan was created by another inspirock user.  Make it your plan

Route & dates

39 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Milan
— 1 day
train:  3​h
2
Rome
— 6 nights
train:  1​h 15​min
3
Naples
— 5 nights
bus:  1​h 15​min
4
Positano
— 5 nights
Drive:  4​h 45​min
5
Assisi
— 5 nights
Drive:  2​h 15​min
6
Florence
— 5 nights
train:  1​h 45​min
7
Verona
— 5 nights
bus:  1​h 15​min
8
Venice
— 6 nights
Fly:  11​h 15​min
End: Toronto

1
day
Milan

Milan ©
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.

Things to do in Milan

Historic Sites Shopping Museums
Find places to stay May 28 — 29:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Castello Sforzesco ©
Castello Sforzesco
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II

6
nights
Rome

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.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trips

Vatican City, Tivoli
Find places to stay May 28 — Jun 3:
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums
Pantheon ©
Pantheon

5
nights
Naples

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.

Things to do in Naples

Historic Sites Museums Shopping

Side Trips

Pompeii Archaeological Park, Parco Acheologico di Ercolano
Find places to stay Jun 3 — 8:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Museo Cappella Sansevero ©
Museo Cappella Sansevero

5
nights
Positano

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.

Things to do in Positano

Parks Beaches Outdoors

Side Trips

Ravello, Vietri sul Mare, Il Gusto della Costa, Lido Capo di Conca, Duomo di Sant'Andrea
Find places to stay Jun 8 — 13:
Highlights from your plan
Spiaggia di castiglione ©
Spiaggia di castiglione
Duomo di Ravello ©
Duomo di Ravello
Lido di Ravello ©
Lido di Ravello

5
nights
Assisi

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.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Azienda Agraria Guerrieri, Museo del Pianoforte Storico e del Suono, Vineria del Carmine, Montioni Frantoio e Cantina
Find places to stay Jun 13 — 18:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Museo della Porziuncola ©
Museo della Porziuncola

5
nights
Florence

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.

Things to do in Florence

Historic Sites Museums Wineries

Side Trips

Guardastelle Vineyard, Duomo di Siena, Castello del Trebbio
Find places to stay Jun 18 — 23:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

5
nights
Verona

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.

Things to do in Verona

Historic Sites Wineries Museums
Find places to stay Jun 23 — 28:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore
Museo di Castelvecchio ©
Museo di Castelvecchio

6
nights
Venice

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.

Things to do in Venice

Historic Sites Museums Shopping

Side Trip

Padua
Find places to stay Jun 28 — Jul 4:
Highlights from your plan
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

Similar Plans

40 days in Italy BY A USER FROM INDIA May, outdoors, romantic, beaches, popular & hidden gems PREFERENCES: May, outdoors, romantic, beaches ATTRACTION STYLE: Popular & hidden gems PACE: Medium 40 days in Italy BY A USER FROM EGYPT December, kids, popular sights PREFERENCES: December, kids ATTRACTION STYLE: Popular sights PACE: Medium 37 days in Italy BY A USER FROM CÔTE D'IVOIRE December, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, slow & easy, popular sights PREFERENCES: December, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 42 days in Europe BY A USER FROM UNITED STATES May, slow & easy, popular & hidden gems PREFERENCES: May ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 40 days in Europe BY A USER FROM UNITED STATES May, outdoors, relaxing, romantic, beaches, shopping, wildlife, popular sights PREFERENCES: May, outdoors, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 37 days in Europe BY A USER FROM AUSTRALIA April, kids, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: April, kids, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 44 days in Croatia & Italy BY A USER FROM AUSTRALIA January, culture, historic sites, museums, popular sights PREFERENCES: January, culture, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 60 days in Italy BY A USER FROM SRI LANKA April, slow & easy, popular & hidden gems PREFERENCES: April ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 37 days in Italy BY A USER FROM VIETNAM December, teens, kids, popular sights PREFERENCES: December, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 60 days in Italy BY A USER FROM INDIA July, relaxing, romantic, beaches, slow & easy, hidden gems PREFERENCES: July, relaxing, romantic, beaches ATTRACTION STYLE: Hidden gems PACE: Slow & easy 59 days in Italy BY A USER FROM UNITED KINGDOM June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 53 days in Germany, Italy & Madrid BY A USER FROM TRINIDAD AND TOBAGO May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans