50 days in Italy Itinerary

50 days in Italy Itinerary

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Route & dates

50 days in Italy Itinerary

Start: Toronto
Fly:  11​h 15​min
1
Milan
— 3 nights
train:  1​h 15​min
2
Verona
— 4 nights
bus:  1​h 30​min
3
Venice
— 6 nights
train:  2​h 15​min
4
Florence
— 6 nights
bus:  1​h 15​min
5
Siena
— 5 nights
Drive:  1​h 45​min
6
Assisi
— 5 nights
Drive:  4​h 45​min
7
Positano
— 6 nights
ferry:  1​h 30​min
8
Salerno
— 6 nights
train:  1​h 45​min
9
Rome
— 7 nights
Fly:  8​h
End: Tallinn

3
nights
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.
Milan is known for historic sites, museums, nightlife, fun & games, and shopping. Your plan includes some of its best attractions: take in the spiritual surroundings of Duomo di Milano, buy something for everyone on your list at Galleria Vittorio Emanuele II, explore the world behind art at Pinacoteca Ambrosiana, and make a trip to Piazza del Duomo.

To see where to stay, more things to do, ratings, and other tourist information, refer to the Milan day trip website .

Toronto, Canada to Milan is an approximately 11.5-hour flight. You can also do a combination of ferry and flight; or do a combination of flight and train. Due to the time zone difference, you'll lose 6 hours traveling from Toronto to Milan. In July in Milan, expect temperatures between 34°C during the day and 21°C at night. Finish your sightseeing early on the 10th (Fri) so you can take a train to Verona.

Things to do in Milan

Historic Sites Museums Fun & Games
Find places to stay Jul 7 — 10:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

4
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.
Explore the numerous day-trip ideas around Verona: Gruppo Dolomitico Sciliar-Catinaccio, Latemar - UNESCO (in Trento) and Lago di Garda (in Garda). There's much more to do: see the grandeur of opera at Arena di Verona, take a stroll through Piazza delle Erbe, make a trip to Piazza Bra, and get the lay of the land with Walking tours.

To find photos, ratings, and other tourist information, refer to the Verona trip maker tool .

You can take a train from Milan to Verona in 1.5 hours. Alternatively, you can drive. In July, daily temperatures in Verona can reach 36°C, while at night they dip to 22°C. Finish up your sightseeing early on the 14th (Tue) so you can catcht the bus to Venice.

Things to do in Verona

Parks Nature Tours

Side Trips

Lago di Garda, Gruppo Dolomitico Sciliar-Catinaccio, Latemar - UNESCO
Find places to stay Jul 10 — 14:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore

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.
Explore Venice's surroundings by going to Padua (Basilica di Sant’Antonio, Scrovegni Chapel, & more). Next up on the itinerary: explore the activities along Canal Grande, enjoy breathtaking views from St Mark's Campanile, don't miss a visit to Piazza San Marco, and admire the masterpieces at Gallerie dell'Accademia.

To find where to stay, more things to do, traveler tips, and tourist information, go to the Venice online visit planner .

Getting from Verona to Venice by bus takes about 1.5 hours. Other options: drive; or take a shuttle. In July, daytime highs in Venice are 36°C, while nighttime lows are 22°C. Finish up your sightseeing early on the 20th (Mon) so you can catch the train to Florence.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay Jul 14 — 20:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Piazza San Marco ©
Piazza San Marco

6
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Venture out of the city with trips to Basilica San Vitale (in Ravenna), Castello del Trebbio (in Santa Brigida) and Leaning Tower of Pisa (in Pisa). There's still lots to do: examine the collection at Academy Of Florence Art Gallery, appreciate the extensive heritage of Piazza del Duomo, get engrossed in the history at Basilica di Santa Croce, and take in nature's colorful creations at The Boboli Gardens.

For reviews, where to stay, ratings, and more tourist information, refer to the Florence trip itinerary builder tool .

Getting from Venice to Florence by train takes about 2.5 hours. Other options: drive; or take a bus. In July, daily temperatures in Florence can reach 35°C, while at night they dip to 21°C. Wrap up your sightseeing on the 26th (Sun) early enough to take a bus to Siena.

Things to do in Florence

Tours Historic Sites Museums

Side Trips

Castello del Trebbio, Leaning Tower of Pisa, Basilica San Vitale
Find places to stay Jul 20 — 26:
Highlights from your plan
Food Tours
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

5
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Explore the numerous day-trip ideas around Siena: Guardastelle Vineyard (in San Gimignano), Winery Solaria Patrizia Cencioni (in Montalcino) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). The adventure continues: make a trip to Piazza del Campo, browse the collection at Biblioteca Piccolomini, let your taste buds guide you at a local gastronomic tour, and take in the architecture and atmosphere at Duomo di Siena.

To see other places to visit, where to stay, maps, and more tourist information, refer to the Siena travel planner.

Traveling by bus from Florence to Siena takes 1.5 hours. Alternatively, you can drive; or take a train. July in Siena sees daily highs of 37°C and lows of 22°C at night. Finish your sightseeing early on the 31st (Fri) so you can drive to Assisi.

Things to do in Siena

Historic Sites Tours Wineries

Side Trips

Montalcino, Guardastelle Vineyard, Batzella
Find places to stay Jul 26 — 31:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

5
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
You'll find plenty of places to visit near Assisi: Montioni Frantoio e Cantina (in Montefalco), Decugnano dei Barbi (in Orvieto) and Azienda Agraria Guerrieri (in Piagge). The adventure continues: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, take in the spiritual surroundings of Basilica di Santa Maria degli Angeli - Porziuncola, examine the collection at Museo della Porziuncola, and stroll around Piana di Castelluccio di Norcia.

To find where to stay, ratings, photos, and tourist information, read our Assisi online trip itinerary builder .

Getting from Siena to Assisi by car takes about 2 hours. Other options: take a bus; or take a train. In July in Assisi, expect temperatures between 37°C during the day and 20°C at night. Finish up your sightseeing early on the 5th (Wed) so you can go by car to Positano.

Things to do in Assisi

Wineries Historic Sites Museums

Side Trips

Perugia, Decugnano dei Barbi, Azienda Agraria Guerrieri, Montioni Frantoio e Cantina, Piana di Castelluccio di Norcia
Find places to stay Jul 31 — Aug 5:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Azienda Agraria Saio ©
Azienda Agraria Saio

6
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.
Change things up with these side-trips from Positano: Amalfi (Wine Tours & Tastings, Speed Boats Tours, & more), Lido di Ravello (in Castiglione) and Ravello (Duomo di Ravello, Villa Rufolo, & more). There's lots more to do: kick back and relax at Fornillo, tour the pleasant surroundings at Lido Capo di Conca, make a trip to Ruga Nova Mercatorum (Via dei Mercanti), and appreciate the history behind Fontana sant'Andrea.

To find more things to do, ratings, traveler tips, and more tourist information, use the Positano road trip planning site .

You can drive from Assisi to Positano in 5 hours. Other options are to do a combination of train and subway; or take a bus. Traveling from Assisi in August, expect somewhat warmer with lows of 26°C in Positano. Wrap up your sightseeing on the 11th (Tue) early enough to ride a ferry to Salerno.

Things to do in Positano

Outdoors Parks Beaches

Side Trips

Amalfi, Ravello, Praiano, Piazzetta Umberto I, Lido Capo di Conca
Find places to stay Aug 5 — 11:
Highlights from your plan
Fornillo ©
Fornillo
Speed Boats Tours
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens

6
nights
Salerno

While often overshadowed by the Amalfi Coast's array of quaint villages, Salerno has become one of the region's main areas for culture and entertainment, while remaining relatively unmarked by tourism.
You'll find plenty of places to visit near Salerno: Paestum Ruins (in Paestum), Ravello (Le Ville di Ravello & Ceramiche Cosmolena di Margherita di Palma) and Spiaggia di castiglione (in Castiglione). There's much more to do: get a new perspective on things with Boat Tours & Water Sports, enjoy the sand and surf at Marina Di Vietri, get a tailor-made plan with Private Tours, and delve into the distant past at Pompeii Archaeological Park.

To see reviews, where to stay, other places to visit, and tourist information, read Salerno travel itinerary planner.

Ride a ferry from Positano to Salerno in 1.5 hours. Alternatively, you can do a combination of taxi and train; or drive. In August in Salerno, expect temperatures between 34°C during the day and 28°C at night. Cap off your sightseeing on the 17th (Mon) early enough to catch the train to Rome.

Things to do in Salerno

Outdoors Tours Parks

Side Trips

Ravello, Sorrento, Maiori, Vietri sul Mare, Spiaggia Lannio
Find places to stay Aug 11 — 17:
Highlights from your plan
Food Tours
Speed Boats Tours
Pompeii Archaeological Park ©
Pompeii Archaeological Park

7
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Change things up with these side-trips from Rome: Tivoli (Villa d'Este & Villa Adriana). There's lots more to do: delve into the distant past at Colosseum, admire the masterpieces at Galleria Borghese, contemplate the long history of St. Peter's Basilica, and make a trip to Spanish Steps.

To see more things to do, reviews, traveler tips, and tourist information, refer to the Rome journey builder site .

Take a train from Salerno to Rome in 2 hours. Alternatively, you can drive; or take a bus. Plan for slightly colder nights when traveling from Salerno in August since evenings lows in Rome dip to 24°C. Finish up your sightseeing early on the 24th (Mon) so you can travel back home.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Vatican City, Tivoli
Find places to stay Aug 17 — 24:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

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