50 days in Italy Itinerary

50 days in Italy Itinerary

Created using Inspirock Italy trip itinerary builder

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Route & dates

50 days in Italy Itinerary

Start: Santiago
Fly:  17​h 30​min
1
Rome
— 6 nights
Train:  1​h 15​min
2
Naples
— 6 nights
Subway + Taxi:  1​h 30​min
3
Amalfi
— 6 nights
Drive:  4​h 30​min
4
Assisi
— 6 nights
Drive:  2​h 15​min
5
Florence
— 6 nights
Train:  2​h 15​min
6
Venice
— 6 nights
Bus:  1​h 30​min
7
Verona
— 6 nights
Train:  1​h 15​min
8
Milan
— 6 nights
Fly:  20​h
End: Santiago

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.
Change things up with these side-trips from Rome: Tivoli (Villa Adriana & Villa d'Este). Next up on the itinerary: explore the ancient world of Colosseum, contemplate the long history of St. Peter's Basilica, make a trip to Roman Forum, and explore the world behind art at Vatican Museums.

To see other places to visit, traveler tips, maps, and other tourist information, refer to the Rome trip tool .

Santiago, Chile to Rome is an approximately 17.5-hour flight. You can also do a combination of flight and train; or do a combination of bus and flight. The time zone difference moving from Chile Time to Central European Time is 5 hours. In April, daytime highs in Rome are 24°C, while nighttime lows are 11°C. Finish your sightseeing early on the 29th (Wed) so you can take a train to Naples.

Things to do in Rome

Historic Sites Museums Tours

Side Trips

Vatican City, Tivoli
Find places to stay Apr 23 — 29:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

6
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Venture out of the city with trips to Vietri sul Mare (Le Vigne di Raito & Sol’Art Ceramiche), Vivaio Ruoppo (in Sorrento) and Positano (Fishing Charters & Tours, Francesco (Frank) Carpegna - Walking with the Gods, & more). Next up on the itinerary: explore the ancient world of Pompeii Archaeological Park, don't miss a visit to Via dei Mercanti, engage your brain at MUSA - Museo Universitario delle Scienze e delle Arti, and browse the exhibits of Museo Cappella Sansevero.

To find photos, where to stay, reviews, and other tourist information, read our Naples trip builder .

Traveling by train from Rome to Naples takes 1.5 hours. Alternatively, you can drive; or take a bus. April in Naples sees daily highs of 23°C and lows of 13°C at night. Wrap up your sightseeing on the 5th (Tue) to allow time to travel to Amalfi.

Things to do in Naples

Historic Sites Museums Outdoors

Side Trips

Salerno, Positano, Vietri sul Mare, Pompeii Archaeological Park, Vivaio Ruoppo
Find places to stay Apr 29 — May 5:
Highlights from your plan
Miglio Sacro ©
Miglio Sacro
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Fishing Charters & Tours

6
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 Praiano (Parrocchia Di San Gennaro & I Suoni degli Dei - Pelagos), Monte Finestra (in Tramonti) and Positano (Il Sentiero Degli Dei & Tennis Al Settimo Piano). And it doesn't end there: indulge your taste buds at Food & Drink, explore the fascinating underground world of Grotte di Suppraiano, examine the collection at Museo della Carta, and contemplate in the serene atmosphere at Duomo di Ravello.

To find more things to do, other places to visit, and tourist information, refer to the Amalfi trip builder website .

You can do a combination of subway and taxi from Naples to Amalfi in 1.5 hours. Other options are to drive; or take a bus. Traveling from Naples in May, you can expect nighttime temperatures to be a bit warmer in Amalfi, with lows of 21°C. Finish up your sightseeing early on the 11th (Mon) so you can go by car to Assisi.

Things to do in Amalfi

Historic Sites Parks Outdoors

Side Trips

Ravello, Praiano, Positano, Conca dei Marini, Chiesa di San Francesco
Find places to stay May 5 — 11:
Highlights from your plan
Villa Rufolo ©
Villa Rufolo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
I Suoni degli Dei - Pelagos ©
I Suoni degli Dei - Pelagos

6
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Explore the numerous day-trip ideas around Assisi: Montioni Frantoio e Cantina (in Montefalco), Azienda Agricola Leuta (in Pietraia) and Ciacci Piccolomini d'Aragona (in Castelnuovo dell'Abate). And it doesn't end there: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, step into the grandiose world of Rocca Maggiore, do a tasting at Bibenda Assisi, and appreciate the extensive heritage of Centro Storico.

To see photos, where to stay, and tourist information, refer to the Assisi trip planner .

Traveling by car from Amalfi to Assisi takes 4.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Traveling from Amalfi in May, plan for slightly colder nights in Assisi, with lows around 13°C. Cap off your sightseeing on the 17th (Sun) early enough to go by car to Florence.

Things to do in Assisi

Historic Sites Wineries Museums

Side Trips

Montioni Frantoio e Cantina, Museo-Laboratorio di Vetrate Artistiche Moretti Caselli, Azienda Agricola Leuta, Val d'Orcia, Ciacci Piccolomini d'Aragona
Find places to stay May 11 — 17:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Azienda Agraria Saio ©
Azienda Agraria Saio

6
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You'll find plenty of places to visit near Florence: Leaning Tower of Pisa (in Pisa) and Siena (Piazza del Campo & Duomo di Siena). The adventure continues: explore the world behind art at Gallerie Degli Uffizi, get great views at Piazzale Michelangelo, admire the striking features of Campanile di Giotto, and steep yourself in history at The Baptistery of St. John.

For where to stay, traveler tips, ratings, and tourist information, refer to the Florence trip itinerary planning site .

Traveling by car from Assisi to Florence takes 2.5 hours. Alternatively, you can take a train. In May in Florence, expect temperatures between 25°C during the day and 13°C at night. Finish your sightseeing early on the 23rd (Sat) so you can take a train to Venice.

Things to do in Florence

Historic Sites Tours Museums

Side Trips

Siena, Leaning Tower of Pisa
Find places to stay May 17 — 23:
Highlights from your plan
Food Tours
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

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.
Get out of town with these interesting Venice side-trips: Padua (Scrovegni Chapel & Basilica di Sant’Antonio). There's lots more to do: contemplate the waterfront views at Canal Grande, browse the exhibits of Peggy Guggenheim Collection, admire the landmark architecture of St Mark's Campanile, and see the interesting displays at Museo Ebraico di Venezia.

To find more things to do, traveler tips, maps, and tourist information, you can read our Venice day trip planning tool .

Getting from Florence to Venice by train takes about 2.5 hours. Other options: drive; or take a bus. In May in Venice, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 29th (Fri) to allow enough time to take a bus to Verona.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay May 23 — 29:
Highlights from your plan
Canal Grande ©
Canal Grande
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

6
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.
Step out of Verona with an excursion to Scuola Italiana di Sci & Snowboard Kristal in Andalo--about 1h 30 min away. Next up on the itinerary: see the grandeur of opera at Arena di Verona, test your problem-solving skills at popular escape rooms, don't miss a visit to Piazza Bra, and wander the streets of Piazza delle Erbe.

Make your Verona itinerary with Inspirock to find out what to see and where to go.

Take a bus from Venice to Verona in 1.5 hours. Alternatively, you can drive; or take a shuttle. In May, plan for daily highs up to 27°C, and evening lows to 13°C. Finish your sightseeing early on the 4th (Thu) to allow enough time to take a train to Milan.

Things to do in Verona

Historic Sites Wineries Outdoors

Side Trip

Scuola Italiana di Sci & Snowboard Kristal
Find places to stay May 29 — Jun 4:
Highlights from your plan
Arena di Verona ©
Arena di Verona
Piazza delle Erbe ©
Piazza delle Erbe
Museo di Castelvecchio ©
Museo di Castelvecchio

6
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.
Venture out of the city with trips to Aquarium of Genoa (in Genoa), Mandello del Lario (Chiesa di San Giorgio & Anything But Work) and Museo Egizio (in Turin). There's still lots to do: take in the spiritual surroundings of Duomo di Milano, admire the masterpieces at Pinacoteca Ambrosiana, explore the historical opulence of Castello Sforzesco, and admire the verdant scenery at Valchiavenna.

To find traveler tips, where to stay, photos, and more tourist information, use the Milan trip itinerary builder tool .

You can take a train from Verona to Milan in 1.5 hours. Alternatively, you can drive. June in Milan sees daily highs of 33°C and lows of 20°C at night. Finish up your sightseeing early on the 10th (Wed) so you can travel back home.

Things to do in Milan

Parks Outdoors Trails

Side Trips

Mandello del Lario, Museo Egizio, Aquarium of Genoa, Sentee di Sort, Villa del Balbianello
Find places to stay Jun 4 — 10:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Aquarium of Genoa ©
Aquarium of Genoa

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