50 days in Italy Itinerary

50 days in Italy Itinerary

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Route & dates

50 days in Italy Itinerary

Start: Santiago
Fly:  20 h
1
Milan
— 1 night
Train:  1 h 15 min
2
Verona
— 5 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
— 6 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:  17 h 30 min
End: Santiago

1
night
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 4th (Mon): contemplate the long history of Castello Sforzesco. Keep things going the next day: admire the masterpieces at Pinacoteca Ambrosiana, take in the architecture and atmosphere at Chiesa di San Maurizio al Monastero Maggiore, then take in the spiritual surroundings of Duomo di Milano, and finally admire the landmark architecture of Galleria Vittorio Emanuele II.

To see where to stay, photos, traveler tips, and tourist information, read our Milan holiday maker app.

Santiago, Chile to Milan is an approximately 20- hour flight. You can also do a combination of flight and train. The time zone difference moving from Chile Time (CLT) to Central European Time (CET) is 5 hours. In mayo in Milan, expect temperatures between 26°C during the day and 15°C at night. Wrap up your sightseeing on the 5th (Tue) to allow time to take a train to Verona.

Things to do in Milan

Historic Sites Museums Shopping
Find places to stay May 4 — 5:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

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.
You'll find plenty of places to visit near Verona: Parma (Caseificio San Pier Damiani & Cattedrale di Parma). Next up on the itinerary: experience the emotional art of opera at Arena di Verona, step into the grandiose world of Museo di Castelvecchio, wander the streets of Quinzano, and get the lay of the land with Walking tours.

To see more things to do, maps, photos, and tourist information, you can read our Verona online driving holiday planner.

You can take a train from Milan to Verona in 1.5 hours. Another option is to drive. In mayo, daily temperatures in Verona can reach 27°C, while at night they dip to 13°C. Finish up your sightseeing early on the 10th (Sun) so you can catch the bus to Venice.

Things to do in Verona

Historic Sites Tours Outdoors

Side Trip

Parma
Find places to stay May 5 — 10:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe
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.
Change things up with these side-trips from Venice: Padua (Basilica di Sant’Antonio, Scrovegni Chapel, &more). Next up on the itinerary: contemplate the waterfront views at Canal Grande, examine the collection at Doge's Palace, take in panoramic vistas at St Mark's Campanile, and take in the views from Ponte di Rialto.

For maps, other places to visit, traveler tips, and tourist information, you can read our Venice attractions planner.

Getting from Verona to Venice by bus takes about 1.5 hours. Other options: drive; or take a shuttle. In mayo in Venice, expect temperatures between 26°C during the day and 15°C at night. Wrap up your sightseeing on the 16th (Sat) early enough to take a train to Florence.

Things to do in Venice

Historic Sites Museums Shopping

Side Trip

Padua
Find places to stay May 10 — 16:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get out of town with these interesting Florence side-trips: Podere Pellicciano - Agrisole (in San Miniato), Leaning Tower of Pisa (in Pisa) and Bologna (Academya Lingue, Basilica - Santuario di Santo Stefano, &more). There's lots more to do: explore the world behind art at Academy Of Florence Art Gallery, take in the architecture and atmosphere at Basilica of Santa Croce, see the interesting displays at Pitti Palace, and make a trip to Piazzale Michelangelo.

For photos and other tourist information, read our Florence road trip planner.

You can take a train from Venice to Florence in 2.5 hours. Alternatively, you can drive; or take a bus. mayo in Florence sees daily highs of 25°C and lows of 13°C at night. Cap off your sightseeing on the 22nd (Fri) early enough to catch the bus to Siena.

Things to do in Florence

Historic Sites Museums Fun & Games

Side Trips

Bologna, Podere Pellicciano - Agrisole, Leaning Tower of Pisa
Find places to stay May 16 — 22:
Highlights from your plan
Podere Pellicciano - Agrisole ©
Podere Pellicciano - Agrisole
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.
Change things up with these side-trips from Siena: Montalcino (Podere Il Cocco & Mate Winery), Guardastelle Vineyard (in San Gimignano) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). There's still lots to do: don't miss a visit to Piazza del Campo, take in the architecture and atmosphere at Duomo di Siena, explore the world behind art at Museo dell'Opera Metropolitana, and deepen your understanding at Scuola di Cucina di Lella.

To find maps, ratings, photos, and tourist information, go to the Siena travel itinerary planner.

Getting from Florence to Siena by bus takes about 1.5 hours. Other options: drive; or take a train. In mayo, daily temperatures in Siena can reach 27°C, while at night they dip to 13°C. Finish your sightseeing early on the 27th (Wed) so you can drive to Assisi.

Things to do in Siena

Wineries Historic Sites Tours

Side Trips

Montalcino, Guardastelle Vineyard
Find places to stay May 22 — 27:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

6
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Explore Assisi's surroundings by going to Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti (in Perugia), Tenuta Cocci Grifoni (in Ripatransone) and Decugnano dei Barbi (in Orvieto). And it doesn't end there: pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, contemplate the long history of Eremo delle Carceri, learn about winemaking at Tili Vini Societa Agricola, and stroll around Mount Subasio.

To find other places to visit, reviews, ratings, and tourist information, use the Assisi trip planner.

You can drive from Siena to Assisi in 2 hours. Other options are to take a bus; or take a train. In mayo in Assisi, expect temperatures between 26°C during the day and 13°C at night. Finish your sightseeing early on the 2nd (Tue) to allow enough time to drive to Positano.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Perugia, Tenuta Cocci Grifoni, Piana di Castelluccio di Norcia, Decugnano dei Barbi, Montioni Frantoio e Cantina
Find places to stay May 27 — Jun 2:
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.
Get out of town with these interesting Positano side-trips: Parrocchia San Giovanni (in Vietri sul Mare), Amalfi (Duomo di Sant'Andrea & Museo della Carta) and Ravello (Ceramiche d'Arte Carmela, Duomo di Ravello, &more). There's lots more to do: get great views at Il Sentiero Degli Dei, go for a walk through Positano, indulge your senses at some of the top wineries in the area, and head outdoors with I Suoni degli Dei - Pelagos.

For reviews, photos, and tourist information, read our Positano itinerary planner.

Traveling by car from Assisi to Positano takes 5 hours. Alternatively, you can do a combination of train and subway; or take a bus. Traveling from Assisi in junio, expect somewhat warmer with lows of 23°C in Positano. Finish your sightseeing early on the 8th (Mon) to allow enough time to ride a ferry to Salerno.

Things to do in Positano

Parks Outdoors Historic Sites

Side Trips

Amalfi, Ravello, Praiano, Sorrento, S.Maria Maddalena
Find places to stay Jun 2 — 8:
Highlights from your plan
Villa Cimbrone Gardens ©
Villa Cimbrone Gardens
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Villa Rufolo ©
Villa Rufolo

6
nights
Salerno

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.
Venture out of the city with trips to Minori (Liquorificio Mansi Carlo & Fontana dei Leoni), Monte Finestra (in Tramonti) and Chiesa di San Francesco (in Maiori). There's still lots to do: delve into the distant past at Pompeii Archaeological Park, get some thrills on the water with a speed boat tour, learn about winemaking at Le Vigne di Raito, and contemplate in the serene atmosphere at Arciconfraternita della Santissima Annunziata e del Santissimo Rosario.

To find where to stay, photos, other places to visit, and other tourist information, you can read our Salerno trip itinerary planner.

You can ride a ferry from Positano to Salerno in 1.5 hours. Alternatively, you can do a combination of taxi and train; or drive. In junio, daily temperatures in Salerno can reach 30°C, while at night they dip to 26°C. Finish your sightseeing early on the 14th (Sun) so you can take a train to Rome.

Things to do in Salerno

Historic Sites Outdoors Tours

Side Trips

Vietri sul Mare, Minori, Pompeii Archaeological Park, Monte Finestra, Chiesa di San Francesco
Find places to stay Jun 8 — 14:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Speed Boats Tours

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.
Rome is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: delve into the distant past at Colosseum, admire the striking features of Pantheon, admire the masterpieces at Galleria Borghese, and pause for some serene contemplation at St. Peter's Basilica.

For other places to visit, maps, traveler tips, and more tourist information, refer to the Rome online trip planner.

Getting from Salerno to Rome by train takes about 2 hours. Other options: drive; or take a bus. Plan for little chillier nights when traveling from Salerno in junio since evenings lows in Rome dip to 21°C. On the 21st (Sun), you'll have the morning to explore before heading back home.

Things to do in Rome

Historic Sites Museums Shopping

Side Trip

Vatican City
Find places to stay Jun 14 — 21:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

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