50 days in Italy Itinerary

50 days in Italy Itinerary

Created using Inspirock Italy attractions planner

Plan created by another user.Make it yours

Route & dates

1
Venice
— 6 nights
2
Rome
— 7 nights
3
Naples
— 7 nights
4
Amalfi
— 7 nights
5
Assisi
— 6 nights
6
Siena
— 5 nights
7
Florence
— 7 nights
8
Milan
— 3 nights

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 of St. Anthony, Scrovegni Chapel, &more) and Verona (Arena di Verona, Museo di Castelvecchio, &more). There's still lots to do: contemplate the waterfront views at Canal Grande, steep yourself in history at Doge's Palace, browse the exhibits of Peggy Guggenheim Collection, and admire the landmark architecture of Basilica di San Marco.

Plan a Venice trip in moments using our itinerary builder.

Toronto, Canada to Venice is an approximately 11.5-hour flight. You'll lose 6 hours traveling from Toronto to Venice due to the time zone difference. In May in Venice, expect temperatures between °C during the day and °C at night. Finish 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.
You'll find plenty of places to visit near Rome: Tivoli (Villa Adriana & Villa d'Este). Next up on the itinerary: explore the ancient world of Colosseum, get to know the fascinating history of Piazza Navona, admire the local landmark of Trevi Fountain, and savor the flavors at Food & Drink.

To find maps, reviews, traveler tips, and tourist information, refer to the Rome trip builder app.

Traveling by flight from Venice to Rome takes 3.5 hours. Alternatively, you can take a train; or drive. Expect a daytime high around °C in May, and nighttime lows around °C. Finish up your sightseeing early on the 27th (Wed) so you can catch the 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
St. Peter's Basilica ©
St. Peter's Basilica

7
nights
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get out of town with these interesting Naples side-trips: Wine Tours & Tastings (in Sorrento), Villa dei Misteri (in Pompeii) and Salerno (Cilento, Chiesa di Sant'Agostino, &more). And it doesn't end there: delve into the distant past at Pompeii Archaeological Park, view the masterpieces at Sol’Art Ceramiche, pause for some serene contemplation at Duomo di Napoli, and see the interesting displays at Museo Archeologico Nazionale di Napoli.

To find photos, reviews, where to stay, and more tourist information, go to the Naples road trip website.

Take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. In May, daytime highs in Naples are °C, while nighttime lows are °C. Wrap up your sightseeing on the 3rd (Wed) to allow time to drive to Amalfi.

Things to do in Naples

Historic Sites Tours Museums

Side Trips

Salerno, Vietri sul Mare, Pompeii, Wine Tours & Tastings, Francesco (Frank) Carpegna - Walking with the Gods
Find places to stay May 27 — Jun 3:
Highlights from your plan
Wine Tours & Tastings
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Paestum Ruins ©
Paestum Ruins

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.
Venture out of the city with trips to Positano (Fornillo & Il Sentiero Degli Dei), Monte Finestra (in Tramonti) and Chiesa San Pietro Apostolo (in Cetara). There's lots more to do: take in nature's colorful creations at Villa Cimbrone Gardens, contemplate in the serene atmosphere at Duomo di Sant'Andrea, view the masterpieces at Ceramiche Cosmolena di Margherita di Palma, and cast your line with a fishing tour.

For photos, ratings, other places to visit, and tourist information, you can read our Amalfi road trip website.

You can drive from Naples to Amalfi in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. Traveling from Naples in June, you can expect nighttime temperatures to be somewhat warmer in Amalfi, with lows of °C. Finish your sightseeing early on the 10th (Wed) to allow enough time to drive to Assisi.

Things to do in Amalfi

Historic Sites Outdoors Tours

Side Trips

Ravello, Positano, Minori, Maiori, Parrocchia San Giovanni
Find places to stay Jun 3 — 10:
Highlights from your plan
Ceramiche Cosmolena di Margherita di Palma ©
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei

6
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Change things up with these side-trips from Assisi: Piana di Castelluccio di Norcia (in Castelluccio di Norcia), Montioni Frantoio e Cantina (in Montefalco) and Vineria del Carmine (in La Bruna). Next up on the itinerary: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, learn about winemaking at Tili Vini Societa Agricola, take in the spiritual surroundings of San Damiano, and see the interesting displays at Museo della Porziuncola.

For more things to do, other places to visit, where to stay, and tourist information, use the Assisi tour builder tool.

Traveling by car from Amalfi to Assisi takes 4.5 hours. Alternatively, you can do a combination of taxi, subway, and train; or do a combination of bus and train. Plan for little chillier nights when traveling from Amalfi in June since evenings lows in Assisi dip to °C. Finish your sightseeing early on the 16th (Tue) to allow enough time to drive to Siena.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

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

5
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You'll find plenty of places to visit near Siena: Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate) and Guardastelle Vineyard (in San Gimignano). There's still lots to do: awaken your taste buds at some of the top wineries in the area, admire the masterpieces at Museo dell'Opera Metropolitana, gain insight at Scuola di Cucina di Lella, and ponder the world of politics at Palazzo Pubblico and Museo Civico.

To see other places to visit, where to stay, reviews, and tourist information, use the Siena trip planner.

Traveling by car from Assisi to Siena takes 2 hours. Alternatively, you can take a bus; or take a train. In June, daily temperatures in Siena can reach °C, while at night they dip to °C. Cap off your sightseeing on the 21st (Sun) early enough to go by car to Florence.

Things to do in Siena

Wineries Historic Sites Tours

Side Trips

Guardastelle Vineyard, Ciacci Piccolomini d'Aragona, Fattoria Pianporcino
Find places to stay Jun 16 — 21:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Guardastelle Vineyard ©
Guardastelle Vineyard
Wine Tours & Tastings

7
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Fattoria al Dotto (in Lucca), Castello del Trebbio (in Santa Brigida) and Leaning Tower of Pisa (in Pisa). And it doesn't end there: explore the world behind art at Florence Academy of Fine Arts, pause for some serene contemplation at Cathedral of Santa Maria del Fiore, contemplate the long history of Basilica of Santa Croce, and don't miss a visit to Piazzale Michelangelo.

To see more things to do, ratings, other places to visit, and more tourist information, refer to the Florence trip itinerary builder.

Traveling by car from Siena to Florence takes 1.5 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to °C, and evening lows to °C. Wrap up your sightseeing on the 28th (Sun) to allow time to take a train to Milan.

Things to do in Florence

Tours Historic Sites Wineries

Side Trips

Fattoria al Dotto, Castello del Trebbio, Leaning Tower of Pisa
Find places to stay Jun 21 — 28:
Highlights from your plan
Food Tours
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts
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.
Explore the numerous day-trip ideas around Milan: Anything But Work (in Mandello del Lario) and Villa del Balbianello (in Tremezzina). The adventure continues: take in the spiritual surroundings of Duomo di Milano, explore the world behind art at Pinacoteca Ambrosiana, appreciate the views at Valchiavenna, and step into the grandiose world of Castello Sforzesco.

To find traveler tips, ratings, photos, and tourist information, refer to the Milan trip planner.

Traveling by train from Florence to Milan takes 2.5 hours. Alternatively, you can drive; or fly. In June, daytime highs in Milan are °C, while nighttime lows are °C. Finish up your sightseeing early on the 1st (Wed) so you can travel back home.

Things to do in Milan

Parks Outdoors Trails

Side Trips

Anything But Work, Valchiavenna, Villa del Balbianello
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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