49 days in Italy Itinerary

49 days in Italy Itinerary

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Route & dates

49 days in Italy Itinerary

Start: Santiago
Fly:  20​h
1
Milan
— 3 nights
train:  1​h 45​min
2
Genoa
— 6 nights
train:  1​h 15​min
3
Cinque Terre
— 2 nights
Drive:  4​h
4
Trento
— 5 nights
Drive:  2​h 15​min
5
Venice
— 6 nights
Drive:  1​h 45​min
6
Bologna
— 4 nights
train:  45​min
7
Florence
— 5 nights
Drive:  2​h 15​min
8
Assisi
— 4 nights
Drive:  2​h 15​min
9
Rome
— 4 nights
train:  1​h 15​min
10
Naples
— 4 nights
+2
Fly + shuttle + train:  5​h 15​min
11
Ravenna
— 2 nights
+2
train + shuttle + Fly:  29​h
End: Santiago

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.
Satisfy your inner culture vulture at Tempio Civico della Beata Vergine Incoronata and Basilica di San Simpliciano. You'll explore the less-touristy side of things at Duomo di Lodi and Basilica di San Vittore al Corpo. Step out of Milan with an excursion to Basilica Santa Maria della Croce in Crema--about 1h 05 min away. Next up on the itinerary: take in the architecture and atmosphere at Chiesa di Sant'Alessandro in Zebedia, take in the spiritual surroundings of Associazione La Grangia Di Monluè, steep yourself in history at Palazzo Clerici, and take an in-depth tour of Memoriale Della Shoah Di Milano.

To find maps, other places to visit, more things to do, and other tourist information, use the Milan trip planning website .

Santiago, Chile to Milan is an approximately 20-hour flight. You can also do a combination of flight and train. The time zone difference when traveling from Santiago to Milan is 5 hours. In April in Milan, expect temperatures between 22°C during the day and 9°C at night. Wrap up your sightseeing on the 26th (Sun) early enough to take a train to Genoa.

Things to do in Milan

Historic Sites Museums

Side Trips

Lodi, Basilica Santa Maria della Croce
Highlights from your plan
Basilica Santa Maria della Croce ©
Basilica Santa Maria della Croce
Duomo di Lodi ©
Duomo di Lodi

6
nights
Genoa

Genoa ©
Once the most important harbor in the Mediterranean Sea, Genoa has a long history as a rich and powerful trade center in northern Italy.
Get some historical perspective at Centro Storico Zuccarello and Castello Mackenzie. Cattedrale di Nostra Signora Assunta and S. Nicolò di Capodimonte are good opportunities to explore the local culture. Explore the numerous day-trip ideas around Genoa: Museo Diocesano e Battistero Paleocristiano (in Albenga) and Santuario di N.S. di Misericordia (in Savona). And it doesn't end there: explore the world behind art at Museo d'Arte Orientale Edoardo Chiossone, examine the collection at Museo del Risorgimento Istituto Mazziniano, take in the spiritual surroundings of Santuario della Madonna del Monte, and take in the architecture and atmosphere at Abbazia di San Siro di Struppa.

To see where to stay, traveler tips, maps, and more tourist information, read our Genoa vacation planning app .

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

Things to do in Genoa

Historic Sites Museums Neighborhoods

Side Trips

Savona, Camogli, Centro Storico Zuccarello, Museo Diocesano e Battistero Paleocristiano
Highlights from your plan
San Pietro in Banchi ©
San Pietro in Banchi
Santuario di N.S. di Misericordia ©
Santuario di N.S. di Misericordia
S. Nicolò di Capodimonte ©
S. Nicolò di Capodimonte

2
nights
Cinque Terre

Cinque Terre ©
Made up of five picturesque towns on the Ligurian coast, Cinque Terre is Italy's answer to the French Riviera.
Visiting Trail 531 Riomaggiore to Manarola and Marigola Beach will get you outdoors. Deepen your sense of the past at sights like Centro Storico del Paese di Tellaro and Via dell'Amore. Change things up with a short trip to Museo Tecnico Navale della Spezia in La Spezia (about 50 minutes away). There's lots more to do: appreciate the extensive heritage of Borgo Storico di Corniglia, take in the architecture and atmosphere at Church of San Giovanni Battista, take in the spiritual surroundings of Chiesa di San Lorenzo, and do a tasting at Cinque Terre Walk and Drink.

For other places to visit, photos, reviews, and more tourist information, use the Cinque Terre trip itinerary tool .

Traveling by train from Genoa to Cinque Terre takes 1.5 hours. Alternatively, you can drive; or take a bus. Traveling from Genoa in May, plan for slightly colder nights in Cinque Terre, with lows around 13°C. Wrap up your sightseeing on the 4th (Mon) to allow time to drive to Trento.

Things to do in Cinque Terre

Historic Sites Outdoors Parks

Side Trips

Centro Storico del Paese di Tellaro, Museo Tecnico Navale della Spezia, Marigola Beach
Highlights from your plan
Castello Doria ©
Castello Doria
Centro Storico del Paese di Tellaro ©
Borgo Storico di Corniglia ©
Borgo Storico di Corniglia

5
nights
Trento

Trento ©
Tyrol's capital and one of the nation's wealthiest cities, Trento serves as the commercial and cultural center of the region.
Do some cultural sightseeing at Chiesa di San Bartolomeo Apostolo and Palazzo Alberti Poja. Step off the beaten path and head to Sacrario militare di Trento and Piazza di Fiera. You'll find plenty of places to visit near Trento: Merano (Algunder Waalweg Path & Corso Della Liberta). The adventure continues: steep yourself in history at Piazza Dante, examine the collection at Spazio Archeologico Sotterraneo Del Sas, don't miss a visit to Badia di San Lorenzo (Padri Cappuccini), and get to know the fascinating history of Molino Vittoria.

For where to stay, more things to do, and tourist information, you can read our Trento trip itinerary maker .

Drive from Cinque Terre to Trento in 4 hours. Alternatively, you can take a train; or do a combination of train and bus. In May, daily temperatures in Trento can reach 28°C, while at night they dip to 13°C. Finish your sightseeing early on the 9th (Sat) to allow enough time to drive to Venice.

Things to do in Trento

Historic Sites Museums Trails

Side Trips

Merano, Molino Ruatti, Museo Civico di Rovereto
Highlights from your plan
Doss Trento ©
Doss Trento
Molino Ruatti ©
Molino Ruatti
Palazzo Alberti Poja ©
Palazzo Alberti Poja

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.
Military Memorial Redipuglia and Villa Contarini are good opportunities to explore the local culture. You'll explore and learn at Villa Valmarana ai Nani and Palazzo Grassi. Change things up with these side-trips from Venice: Cripta Degli Scavi (in Aquileia), Vicenza (Santuario della Madonna di Monte Berico, Chiesa di Santa Corona, & more) and Santuario Di Barbana Church (in Santuario di Barbana). Next up on the itinerary: contemplate in the serene atmosphere at Santa Maria dei Miracoli, take in the architecture and atmosphere at Chiesa Parrocchiale di San Lorenzo di Fiumicello, make a trip to Sito Paleontologico Dinosauro Antonio, and contemplate the long history of Centro Storico di Treviso.

For photos, maps, ratings, and tourist information, use the Venice travel route planner.

Traveling by car from Trento to Venice takes 2.5 hours. Alternatively, you can take a train; 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 15th (Fri) to allow enough time to drive to Bologna.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Vicenza, Treviso, Military Memorial Redipuglia, Cripta Degli Scavi, Villa Contarini
Highlights from your plan
Military Memorial Redipuglia ©
Military Memorial Redipuglia
Santa Maria dei Miracoli ©
Santa Maria dei Miracoli
Santuario Di Barbana Church ©
Santuario Di Barbana Church

4
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Appreciate the collections at Istituto Storico Parri Emilia Romagna and Casa Carducci. Popular historic sites such as Bologna War Cemetery and Monastero di San Giovanni Evangelista are in your itinerary. Change things up with these side-trips from Bologna: Modena (Galleria Estense, Museo Civico d'Arte, & more). Next up on the itinerary: appreciate the extensive heritage of Strada Maggiore, pause for some serene contemplation at Basilica di Santa Maria dei Servi Bologna, contemplate the long history of Piazza Santo Stefano, and contemplate in the serene atmosphere at Chiesa della Madonna di Galliera.

Take the guesswork out of planning a Bologna vacation by using our trip itinerary maker.

Drive from Venice to Bologna in 2 hours. Alternatively, you can take a train; or take a bus. In May, daily temperatures in Bologna can reach 27°C, while at night they dip to 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

Modena, Monastero di San Giovanni Evangelista
Highlights from your plan
La Macchina del Tempo ©
La Macchina del Tempo
Panini Motor Museum ©
Panini Motor Museum
Museo Civico d'Arte ©
Museo Civico d'Arte

5
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Appreciate the collections at Palazzo Strozzi and Church and Museum of Orsanmichele. Get some historical perspective at Loggia dei Lanzi and Torre e Casa Campatelli. Explore Florence's surroundings by going to La Rocca di Staggia (in Staggia), Casa di Santa Caterina (in Siena) and Parco Sculture Del Chianti (in Pievasciata). And it doesn't end there: get engrossed in the history at Corridoio Vasariano, learn about winemaking at La Cantina di Casalvento, appreciate the extensive heritage of San Gimignano 1300, and take in the spiritual surroundings of Sinagoga di Firenze e Museo ebraico.

To see other places to visit, photos, traveler tips, and more tourist information, use the Florence online vacation planner .

Traveling by train from Bologna to Florence takes an hour. Alternatively, you can take a bus; or drive. In May in Florence, expect temperatures between 25°C during the day and 13°C at night. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Assisi.

Things to do in Florence

Museums Historic Sites Wineries

Side Trips

San Gimignano, Calci, La Rocca di Staggia, Corbucci, Parco Sculture Del Chianti
Highlights from your plan
Palazzo Strozzi ©
Palazzo Strozzi
Corridoio Vasariano ©
Corridoio Vasariano

4
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Let the collections at Museo-Laboratorio di Vetrate Artistiche Moretti Caselli and Museo del Tesoro e Collezione F.M. Perkins capture your imagination. Satisfy your inner culture vulture at Roman Forum and Archaeological Museum and Museo-Laboratorio di Tessitura a Mano Giuditta Brozzetti. There's much more to do: appreciate the extensive heritage of Piazza Superiore di San Francesco, pause for some serene contemplation at Chiesa di San Giacomo De Muro Rotto, steep yourself in history at Casa del Maestri Comacini, and delve into the distant past at Parrocchia Santa Maria Maggiore - Frati Cappuccini Assisi.

For more things to do, traveler tips, photos, and more tourist information, go to the Assisi trip maker app .

You can drive from Florence to Assisi in 2.5 hours. Another option is to take a train. In May in Assisi, expect temperatures between 26°C during the day and 13°C at night. Wrap up your sightseeing on the 28th (Thu) early enough to drive to Rome.

Things to do in Assisi

Historic Sites Museums Shopping

Side Trips

Perugia, Centro Storico
Highlights from your plan

4
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Museum-lovers will appreciate Stanze di Raffaello and Mercati di Traiano - Museo dei Fori Imperiali. Step off the beaten path and head to Chiesa di Santa Maria del Popolo and Piazza del Campidoglio. When in Rome, make a side trip to see Museo Storico dell'Aeronautica Militare in Vigna di Valle, approximately 48 minutes away. There's much more to do: explore the engaging exhibits at Welcome to Rome, explore the galleries of National Gallery of Ancient Art in Barberini Palace, explore the ancient world of Forum of Augustus, and pause for some serene contemplation at Basilica di Santa Prassede.

For other places to visit, reviews, ratings, and more tourist information, use the Rome itinerary planner .

Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in May, plan for somewhat warmer nights in Rome, with lows around 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 Childrens Museums

Side Trips

Vatican City, Museo Storico dell'Aeronautica Militare
Highlights from your plan
Chiesa di Santa Maria del Popolo ©
Chiesa di Santa Maria del Popolo
Stanze di Raffaello ©
Stanze di Raffaello
Colle Aventino ©
Colle Aventino

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore hidden gems such as Villa Floridiana and Museo delle Torture. Your inner history buff will appreciate Cumae (Cuma) and Macellum (Temple of Serapis). Venture out of the city with trips to Sol’Art Ceramiche (in Vietri sul Mare), Rione Terra (in Pozzuoli) and Odeon - Teatro Piccolo (in Pompeii). The adventure continues: explore the world behind art at Madre . museo d'arte contemporanea Donnaregina, take a stroll through Decumani di Napoli, examine the collection at MUSA - Museo Universitario delle Scienze e delle Arti, and make a trip to Oltre I Resti.

To find traveler tips, other places to visit, and other tourist information, read Naples trip itinerary planning app .

Traveling by train from Rome to Naples takes 1.5 hours. Alternatively, you can drive; or take a bus. June in Naples sees daily highs of 32°C and lows of 22°C at night. Finish your sightseeing early on the 5th (Fri) so you can travel back home.

Things to do in Naples

Historic Sites Museums Neighborhoods

Side Trips

Pozzuoli, Pompeii, Sol’Art Ceramiche
Highlights from your plan
Villa Floridiana ©
Villa Floridiana
Rione Terra ©
Rione Terra
Macellum (Temple of Serapis) ©
Macellum (Temple of Serapis)

2
nights
Ravenna

Ravenna ©
Famous for its wealth of original mosaics, Ravenna is a hub of artistic and cultural heritage.
Mar - Museo d'Arte della citta di Ravenna and Castrocaro Fortress are good opportunities to explore the local culture. Get some historical perspective at Antico Porto di Classe and Abbazia di San Mercuriale. Get out of town with these interesting Ravenna side-trips: Palazzo Romagnoli Forli (in Forli), Chiesa di Pieve Tho (in Brisighella) and Bagno Sauro 286 (in Milano Marittima). There's still lots to do: see the interesting displays at Museo Dantesco, pause for some serene contemplation at Basilica di Sant'Agata Maggiore, and contemplate the long history of Cripta Rasponi e Giardini Pensili.

To find reviews, traveler tips, more things to do, and more tourist information, refer to the Ravenna route builder tool .

Traveling by combination of flight and train from Naples to Ravenna takes 5.5 hours. Alternatively, you can take a train; or drive. Traveling from Naples in June, you can expect nighttime temperatures to be a bit cooler in Ravenna, with lows of 19°C. Cap off your sightseeing on the 8th (Mon) early enough to travel back home.

Things to do in Ravenna

Museums Historic Sites Outdoors

Side Trips

Forli, Chiesa di Pieve Tho, Bagno Sauro 286, Castrocaro Fortress
Highlights from your plan
Museo Dantesco ©
Museo Dantesco
Bagno Sauro 286 ©
Bagno Sauro 286
Palazzo Romagnoli Forli ©
Palazzo Romagnoli Forli

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