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
Venice
— 6 nights
Fly:  3​h 15​min
2
Rome
— 7 nights
train:  1​h 15​min
3
Naples
— 7 nights
subway + taxi:  1​h 30​min
4
Amalfi
— 7 nights
Drive:  4​h 30​min
5
Assisi
— 6 nights
Drive:  1​h 45​min
6
Siena
— 5 nights
bus:  1​h 15​min
7
Florence
— 7 nights
train:  1​h 45​min
8
Milan
— 3 nights
Fly:  11​h 15​min
End: Toronto

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.
You'll find plenty of places to visit near Venice: Verona (Arena di Verona, Museo di Castelvecchio, & more) and Padua (Basilica di Sant’Antonio, Scrovegni Chapel, & more). There's much more to do: explore the activities along Canal Grande, appreciate the extensive heritage of Piazza San Marco, take in panoramic vistas at St Mark's Campanile, and admire the masterpieces at Gallerie dell'Accademia.

To see other places to visit, more things to do, maps, and other tourist information, you can read our Venice trip itinerary builder app .

Toronto, Canada to Venice is an approximately 11.5-hour flight. You can also do a combination of flight and train. The time zone difference moving from Eastern Standard Time (EST) to Central European Time (CET) is 6 hours. In May, daily temperatures in Venice can reach 26°C, while at night they dip to 15°C. Finish up your sightseeing early on the 20th (Wed) so you can travel to Rome.

Things to do in Venice

Historic Sites Museums Tours

Side Trips

Verona, Padua
Find places to stay May 13 — 20:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

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.
Venture out of the city with trips to Tivoli (Villa Adriana & Villa d'Este). There's lots more to do: delve into the distant past at Colosseum, make a trip to Roman Forum, contemplate the long history of Palatine Hill, and admire the landmark architecture of Pantheon.

To see more things to do, traveler tips, maps, and tourist information, you can read our Rome trip planner.

Traveling by flight from Venice to Rome takes 3.5 hours. Alternatively, you can take a train; or drive. In May, daytime highs in Rome are 28°C, while nighttime lows are 17°C. Finish your sightseeing early on the 27th (Wed) to allow enough time to take a train to Naples.

Things to do in Rome

Historic Sites Museums Tours

Side Trips

Tivoli, Vatican City
Find places to stay May 20 — 27:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

7
nights
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore the numerous day-trip ideas around Naples: Villa dei Misteri (in Pompeii), Vietri sul Mare (Arciconfraternita della Santissima Annunziata e del Santissimo Rosario & Sol’Art Ceramiche) and Salerno (Cilento, Chiesa di Sant'Agostino, & more). There's much more to do: contemplate the long history of Pompeii Archaeological Park, see the interesting displays at Museo Archeologico Nazionale di Napoli, indulge your senses at some of the top wineries in the area, and don't miss a visit to Miglio Sacro.

To see more things to do, photos, ratings, and other tourist information, read Naples day trip planning tool .

You can take a train from Rome to Naples in 1.5 hours. Other options are to drive; or take a bus. In May, plan for daily highs up to 27°C, and evening lows to 17°C. Finish your sightseeing early on the 3rd (Wed) so you can travel to Amalfi.

Things to do in Naples

Historic Sites Tours Museums

Side Trips

Salerno, Pompeii, Vietri sul Mare, Wine Tours & Tastings, Paestum Ruins
Find places to stay May 27 — Jun 3:
Highlights from your plan
Wine Tours & Tastings
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Speed Boats Tours

7
nights
Amalfi

Amalfi ©
Known for its impressive hillside cascade of colorful stone buildings down to the Mediterranean shore, Amalfi is the cultural and commercial heart of southern Italy's Amalfi Coast.
You'll find plenty of places to visit near Amalfi: Chiesa San Pietro Apostolo (in Cetara), Monte Finestra (in Tramonti) and I Suoni degli Dei - Pelagos (in Praiano). There's lots more to do: indulge your taste buds at Food & Drink, take in nature's colorful creations at Villa Cimbrone Gardens, admire the landmark architecture of Villa Rufolo, and kick back and relax at Fornillo.

For other places to visit, reviews, more things to do, and other tourist information, use the Amalfi itinerary planner .

You can do a combination of subway and taxi from Naples to Amalfi in 1.5 hours. Alternatively, you can drive; or take a bus. Plan for somewhat warmer nights when traveling from Naples in June since evenings lows in Amalfi dip to 26°C. Wrap up your sightseeing on the 10th (Wed) early enough to drive to Assisi.

Things to do in Amalfi

Historic Sites Outdoors Tours

Side Trips

Ravello, Positano, Praiano, Maiori, Minori
Find places to stay Jun 3 — 10:
Highlights from your plan
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Villa Rufolo ©
Villa Rufolo

6
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Venture out of the city with trips to Vineria del Carmine (in La Bruna), Montioni Frantoio e Cantina (in Montefalco) and Piana di Castelluccio di Norcia (in Castelluccio di Norcia). There's much more to do: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, walk around Mount Subasio, do a tasting at Bibenda Assisi, and contemplate in the serene atmosphere at San Damiano.

To see photos, ratings, maps, and more tourist information, read Assisi visit app .

You can drive from Amalfi to Assisi in 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Traveling from Amalfi in June, plan for little chillier nights in Assisi, with lows around 18°C. Finish up your sightseeing early on the 16th (Tue) so you can go by car to Siena.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Perugia, Azienda Agraria Guerrieri, Piana di Castelluccio di Norcia, Montioni Frantoio e Cantina
Find places to stay Jun 10 — 16:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Azienda Agraria Saio ©
Azienda Agraria Saio

5
nights
Siena

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: Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Guardastelle Vineyard (in San Gimignano). And it doesn't end there: make a trip to Piazza del Campo, deepen your understanding at Scuola di Cucina di Lella, let your taste buds guide you at a local gastronomic tour, and admire the masterpieces at Museo dell'Opera Metropolitana.

To find reviews, traveler tips, and tourist information, refer to the Siena trip tool .

Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 34°C, and evening lows to 19°C. Finish up your sightseeing early on the 21st (Sun) so you can catcht the bus to Florence.

Things to do in Siena

Historic Sites Tours Wineries

Side Trips

Guardastelle Vineyard, Ciacci Piccolomini d'Aragona
Find places to stay Jun 16 — 21:
Highlights from your plan
Food Tours
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

7
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore the numerous day-trip ideas around Florence: Castello del Trebbio (in Santa Brigida), Leaning Tower of Pisa (in Pisa) and Fattoria al Dotto (in Lucca). There's still lots to do: see the interesting displays at Academy Of Florence Art Gallery, take in the views from Ponte Vecchio, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and take an in-depth tour of Basilica di Santa Croce.

For ratings, other places to visit, maps, and more tourist information, read Florence road trip site .

You can take a bus from Siena to Florence in 1.5 hours. Alternatively, you can drive; or take a train. June in Florence sees daily highs of 33°C and lows of 21°C at night. Finish your sightseeing early on the 28th (Sun) so you can take a train to Milan.

Things to do in Florence

Tours Museums Historic Sites

Side Trips

Fattoria al Dotto, Leaning Tower of Pisa, Castello del Trebbio
Find places to stay Jun 21 — 28:
Highlights from your plan
Food Tours
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

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.
Get out of town with these interesting Milan side-trips: Anything But Work (in Mandello del Lario) and Villa del Balbianello (in Tremezzina). Next up on the itinerary: pause for some serene contemplation at Duomo di Milano, explore the world behind art at Pinacoteca Ambrosiana, make a trip to Galleria Vittorio Emanuele II, and explore the historical opulence of Castello Sforzesco.

To find photos, other places to visit, reviews, and other tourist information, refer to the Milan trip itinerary planner .

Traveling by train from Florence to Milan takes 2 hours. Alternatively, you can drive; or fly. In June in Milan, expect temperatures between 33°C during the day and 20°C at night. Finish up your sightseeing early on the 1st (Wed) so you can travel back home.

Things to do in Milan

Parks Historic Sites Trails

Side Trips

Valchiavenna, Villa del Balbianello, Anything But Work
Find places to stay Jun 28 — Jul 1:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Villa del Balbianello ©
Villa del Balbianello

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