49 days in Italy Itinerary

49 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

Make it your trip
Fly
1
Milan
— 3 nights
Drive
2
Genoa
— 6 nights
Train
3
Cinque Terre
— 2 nights
Drive
4
Trento
— 5 nights
Drive
5
Venice
— 6 nights
Drive
6
Bologna
— 4 nights
Train
7
Florence
— 5 nights
Drive
8
Assisi
— 4 nights
Drive
9
Rome
— 4 nights
Train
10
Naples
— 4 nights
Train
11
Ravenna
— 2 nights
Fly

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Milan

— 3 nights

Fashion Capital of World

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.
Visit Basilica Santa Maria della Croce and Palazzo Clerici for their historical value. You'll discover tucked-away gems like Tempio Civico della Beata Vergine Incoronata and Memoriale Della Shoah Di Milano. Go for a jaunt from Milan to Lodi to see Duomo di Lodi about 48 minutes away. There's much more to do: take in the architecture and atmosphere at Basilica di San Vittore al Corpo, take in the spiritual surroundings of Associazione La Grangia Di Monluè, and see the interesting displays at The Bramante Sacristy.

For maps, ratings, other places to visit, and tourist information, go to the Milan trip itinerary planning app.

Santiago, Chile to Milan is an approximately 20.5-hour flight. Due to the time zone difference, you'll lose 5 hours traveling from Santiago to Milan. In April, plan for daily highs up to 22°C, and evening lows to 9°C. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Genoa.

Things to do in Milan

Historic Sites · Museums

Side Trips

Genoa

— 6 nights
Once the most important harbor in the Mediterranean Sea, Genoa has a long history as a rich and powerful trade center in northern Italy.
Museo Diocesano e Battistero Paleocristiano and Museo Civico di Storia Naturale Giacomo Doria will appeal to museum buffs. San Pietro in Banchi and Cattedrale di Nostra Signora Assunta will appeal to history buffs. You'll find plenty of places to visit near Genoa: Centro Storico Zuccarello (in Zuccarello), Santuario di N.S. di Misericordia (in Savona) and Camogli (Basilica Di Santa Maria Assunta & S. Nicolò di Capodimonte). There's still lots to do: make a trip to Chiesa Di San Donato, appreciate the extensive heritage of Campopisano, take in the spiritual surroundings of Abbazia di San Siro di Struppa, and examine the collection at Palazzo Doria Tursi.

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

Getting from Milan to Genoa by car takes about 2 hours. Other options: take a train. Expect a bit warmer evenings in Genoa when traveling from Milan in April, with lows around 14°C. Finish up your sightseeing early on the 2nd (Sat) so you can catch the train to Cinque Terre.

Things to do in Genoa

Historic Sites · Museums · Neighborhoods · Childrens Museums

Side Trips

Cinque Terre

— 2 nights

Italian Riviera

Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Step out of the city life by going to Trail 531 Riomaggiore to Manarola and Marigola Beach. Satisfy your inner culture vulture at Centro Storico del Paese di Tellaro and Santa Margherita di Antiochia Church. Take a break from Cinque Terre with a short trip to Museo Tecnico Navale della Spezia in La Spezia, about 50 minutes away. And it doesn't end there: explore the historical opulence of Castello Doria, admire the striking features of Chiesa Di San Pietro, get to know the fascinating history of Borgo Storico di Riomaggiore, and contemplate in the serene atmosphere at Chiesa di San Lorenzo.

To find ratings, traveler tips, maps, and more tourist information, you can read our Cinque Terre trip itinerary website.

Traveling by train from Genoa to Cinque Terre takes 2 hours. Alternatively, you can drive; or do a combination of bus and train. Plan for slightly colder nights when traveling from Genoa in May since evenings lows in Cinque Terre dip to 13°C. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Trento.

Things to do in Cinque Terre

Historic Sites · Parks · Outdoors · Museums

Side Trips

Trento

— 5 nights

Painted City

Tyrol's capital and one of the nation's wealthiest cities, Trento serves as the commercial and cultural center of the region.
Discover out-of-the-way places like Chiesa Santa Maria Maggiore and Doss Trento. Visit Area Archeologica Palazzo Lodron and Piazza Dante for their historical value. Explore Trento's surroundings by going to Corso Della Liberta (in Merano), Molino Ruatti (in Pracorno) and Museo Civico di Rovereto (in Rovereto). There's much more to do: see the interesting displays at Spazio Archeologico Sotterraneo del Sas, stroll the grounds of Chiesa di San Bartolomeo Apostolo, get to know the fascinating history of Piazza di Fiera, and admire the landmark architecture of Molino Vittoria.

To see reviews, other places to visit, photos, and more tourist information, you can read our Trento trip itinerary app.

Traveling by car from Cinque Terre to Trento takes 4 hours. Alternatively, you can take a train; or do a combination of train and bus. In May in Trento, expect temperatures between 28°C during the day and 13°C at night. Finish your sightseeing early on the 9th (Sat) so you can drive to Venice.

Things to do in Trento

Historic Sites · Museums · Wineries

Side Trips

Venice

— 6 nights

City of Romance

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.
Do some cultural sightseeing at Military Memorial Redipuglia and Centro Storico di Treviso. You'll explore the less-touristy side of things at Church of Santa Maria e San Donato and Santuario della Madonna di Monte Berico. Explore Venice's surroundings by going to Vicenza (Villa Valmarana ai Nani, Chiesa di Santa Corona, &more), Cripta Degli Scavi (in Aquileia) and Santuario Di Barbana Church (in Santuario di Barbana). The adventure continues: contemplate in the serene atmosphere at Church of San Pantalon, stroll around Villa Contarini, pause for some serene contemplation at Chiesa San Simeon Piccolo, and contemplate the long history of Sito Paleontologico Dinosauro Antonio.

For more things to do, other places to visit, reviews, and other tourist information, refer to the Venice road trip planner.

You can drive from Trento to Venice in 2.5 hours. Another option is to take a train. In May in Venice, expect temperatures between 26°C during the day and 15°C at night. Cap off your sightseeing on the 15th (Fri) early enough to go by car to Bologna.

Things to do in Venice

Historic Sites · Museums · Parks · Neighborhoods

Side Trips

Bologna

— 4 nights

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
You'll discover tucked-away gems like Monastero di San Giovanni Evangelista and La Macchina del Tempo. Piazza Santo Stefano and Basilica di Santa Maria dei Servi will appeal to history buffs. Explore Bologna's surroundings by going to Modena (Galleria Estense, Museo Civico d'Arte, &more). And it doesn't end there: see the interesting displays at International museum and library of music, contemplate the long history of Palazzo Re Enzo, stop by Salumeria Simoni, and admire the striking features of Palazzo del Podesta.

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

Drive from Venice to Bologna in 2 hours. Alternatively, you can take a train; or take a bus. In May, daytime highs in Bologna are 27°C, while nighttime lows are 14°C. Wrap up your sightseeing on the 19th (Tue) early enough to take a train to Florence.

Things to do in Bologna

Museums · Historic Sites · Shopping

Side Trips

Florence

— 5 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get some cultural insight at Church and Museum of Orsanmichele and Museo di Palazzo Davanzati. You'll discover tucked-away gems like Corridoio Vasariano and Palazzo Strozzi. Change things up with these side-trips from Florence: La Rocca di Staggia (in Staggia), Parco Sculture Del Chianti (in Pievasciata) and Casa di Santa Caterina (in Siena). Next up on the itinerary: contemplate the long history of Torre e Casa Campatelli, get engrossed in the history at Sinagoga di Firenze e Museo ebraico, learn more about the world around you at Museo Nazionale della Certosa Monumentale di Calci, and learn about winemaking at La Cantina di Casalvento.

Discover how to plan a Florence trip in just a few steps with Inspirock's itinerary builder.

Take a train from Bologna to Florence in 1.5 hours. Alternatively, you can drive; or take a bus. In May in Florence, expect temperatures between 25°C during the day and 13°C at night. Wrap up your sightseeing on the 24th (Sun) early enough to drive to Assisi.

Things to do in Florence

Museums · Historic Sites · Wineries · Childrens Museums

Side Trips

Assisi

— 4 nights

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Explore hidden gems such as Centro Storico and Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti. Your cultural itinerary includes sights like Roman Forum and Archaeological Museum and Museo Diocesano e Cripta di San Rufino. Take a break from Assisi with a short trip to Studio Moretti Caselli in Perugia, about 34 minutes away. And it doesn't end there: admire the landmark architecture of Santa Maria sopra Minerva, pause for some serene contemplation at Chiesa di San Giacomo De Muro Rotto, explore the ancient world of Domus Romane di Assisi, and appreciate the extensive heritage of Piazza Superiore di San Francesco.

For photos, reviews, maps, and other tourist information, refer to the Assisi road trip planning site.

Getting from Florence to Assisi by car takes about 2.5 hours. Other options: take a train. In May, daily temperatures in Assisi can reach 26°C, while at night they dip to 13°C. Finish up your sightseeing early on the 28th (Thu) so you can go by car to Rome.

Things to do in Assisi

Historic Sites · Museums · Parks · Shopping

Side Trips

Rome

— 4 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Discover out-of-the-way places like Piazza del Campidoglio and Chiesa di Santa Maria del Popolo. Popular historic sites such as Mercati di Traiano - Museo dei Fori Imperiali and Forum of Augustus are in your itinerary. Step out of Rome with an excursion to Museo Storico dell'Aeronautica Militare in Vigna di Valle--about 48 minutes away. There's still lots to do: take in the architecture and atmosphere at Basilica di Santa Prassede, examine the collection at Complesso del Vittoriano, browse the exhibits of National Gallery of Ancient Art in Barberini Palace, and admire the natural beauty at Monte Pincio.

To see ratings, other places to visit, photos, and other tourist information, read Rome trip planner.

Drive from Assisi to Rome in 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in May, you can expect nighttime temperatures to be a bit warmer in Rome, with lows of 17°C. Finish up your sightseeing early on the 1st (Mon) so you can catch the train to Naples.

Things to do in Rome

Historic Sites · Museums · Parks · Nature

Side Trips

Naples

— 4 nights
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Rione Terra and Macellum (Temple of Serapis) will appeal to history buffs. Step off the beaten path and head to Chiesa dei Santi Filippo e Giacomo - Complesso Museale dell'Arte della Seta and Acquaquiglia del Pozzaro. Venture out of the city with trips to Archaeological site of Cuma (in Pozzuoli) and Pompeii (House of Menander (Casa del Menandro) & Odeon - Teatro Piccolo). There's lots more to do: take in the architecture and atmosphere at Complesso Museale Santa Maria delle Anime del Purgatorio ad Arco, wander the streets of Chiaia, take an in-depth tour of Museo delle Torture, and admire the masterpieces at Madre . museo d'arte contemporanea Donnaregina.

To see photos, ratings, traveler tips, and tourist information, you can read our Naples trip builder app.

You can take a train from Rome to Naples in 2 hours. Alternatively, you can drive; or fly. In June in Naples, expect temperatures between 32°C during the day and 22°C at night. Wrap up your sightseeing on the 5th (Fri) to allow time to take a train to Ravenna.

Things to do in Naples

Historic Sites · Museums · Neighborhoods · Shopping

Side Trips

Ravenna

— 2 nights

City of Mosaics

Famous for its wealth of original mosaics, Ravenna is a hub of artistic and cultural heritage.
Let the collections at Mar - Museo d'Arte della citta di Ravenna and Pinacoteca Comunale capture your imagination. Do some cultural sightseeing at Castrocaro Fortress and Cripta Rasponi e Giardini Pensili. Venture out of the city with trips to Forli (Palazzo Romagnoli Forli & Abbazia di San Mercuriale), Chiesa di Pieve Tho (in Brisighella) and Bagno Sauro 286 (in Milano Marittima). There's still lots to do: explore the ancient world of Antico Porto di Classe, pause for some serene contemplation at Basilica di Sant'Agata Maggiore, and see the interesting displays at Tamo Museo del Mosaico.

For photos, maps, traveler tips, and more tourist information, use the Ravenna route planner.

Take a train from Naples to Ravenna in 5 hours. Alternatively, you can drive; or do a combination of train and flight. Plan for a bit cooler nights when traveling from Naples in June since evenings lows in Ravenna dip to 19°C. Finish up your sightseeing early on the 8th (Mon) so you can travel back home.

Things to do in Ravenna

Museums · Historic Sites · Beaches · Parks

Side Trips

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.