45 days in Italy Itinerary

45 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

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Route & dates

45 days in Italy Itinerary

Start: Chicago
Fly + train:  14​h
1
Naples
— 4 nights
bus:  15​min
2
Pompeii
— 2 nights
Drive:  45​min
3
Positano
— 2 nights
Drive:  1​h
4
Anacapri, Island of Capri
— 2 nights
+4
ferry + foot + subway + foot + train:  3​h 15​min
5
Rome
— 16 nights
Fly:  2​h 15​min
6
Pisa
— 2 nights
train:  1​h
7
Florence
— 4 nights
train:  1​h 45​min
8
Milan
— 3 nights
train:  2​h 45​min
9
Venice
— 7 nights
Fly:  14​h
End: Chicago

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Your list of things to see and do now includes Santuario dell'Addolorata di Castelpetroso, Cumae (Cuma), Reggia di Caserta, and other attractions. You'll discover tucked-away gems like Museo Nazionale del Paleolitico and Scavi Archeologici di Ercolano. Chiesa di San Giovanni a Carbonara and Napoli Sotterranea will appeal to history buffs.

To see where to stay, more things to do, traveler tips, and tourist information, read Naples travel planner.

Chicago, USA to Naples is an approximately 14-hour combination of flight and train. You can also fly. You'll lose 7 hours traveling from Chicago to Naples due to the time zone difference. Traveling from Chicago in April, things will get somewhat warmer in Naples: highs are around 68°F and lows about 52°F. Finish your sightseeing early on the 6th (Fri) to allow enough time to drive to Pompeii.

Things to do in Naples

Historic Sites Parks Museums

Side Trips

Museo Nazionale del Paleolitico, Santuario dell'Addolorata di Castelpetroso, Vesuvio National Park, Cumae (Cuma), Reggia di Caserta
Find places to stay Apr 2 — 6:
Highlights from your plan
Catacombe di San Gennaro ©
Catacombe di San Gennaro
Underground Naples ©
Underground Naples

2
nights
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
You've added Paestum Ruins, Temple of Jupiter, Temple of Apollo, and other attractions to your itinerary. Start off your visit on the 7th (Sat): explore the ancient world of Casa del Fauno, explore the ancient world of Paestum Ruins, get engrossed in the history at Museo Vesuviano Giovan Battista Alfano, explore the ancient world of House of Menander (Casa del Menandro), then admire the landmark architecture of Villa dei Misteri, and finally explore the ancient world of Casa del Poeta Tragico. Here are some ideas for day two: explore the ancient world of Scavi di Stabia, delve into the distant past at Temple of Apollo, get engrossed in the history at Antiquarium and Excavations, then explore the ancient world of Odeon - Teatro Piccolo, then explore the ancient world of Tempio d'Iside, and finally explore the ancient world of Teatro Grande.

For other places to visit, where to stay, and tourist information, read our Pompeii attractions site .

Pompeii is very close to Naples. Expect a daytime high around 67°F in April, and nighttime lows around 52°F. Finish your sightseeing early on the 8th (Sun) to allow enough time to drive to Positano.

Things to do in Pompeii

Historic Sites Museums

Side Trips

Antiquarium and Excavations, Paestum Ruins, Scavi di Stabia
Find places to stay Apr 6 — 8:
Highlights from your plan
Villa dei Misteri ©
Villa dei Misteri
Paestum Ruins ©
Paestum Ruins
Scavi di Stabia ©
Scavi di Stabia

2
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.
You've added Bagni d'Arienzo, Il Tempio di Nettuno o Poseidone o di Hera II, Castello di Arechi, and other attractions to your itinerary. Get ready for a full day of sightseeing on the 9th (Mon): contemplate the long history of Il Tempio di Nettuno o Poseidone o di Hera II, look for all kinds of wild species at Valle delle Ferriere, then don't miss a visit to Le Ville di Ravello, and finally make a trip to Villa Rufolo.

To find more things to do, maps, traveler tips, and tourist information, refer to the Positano trip site .

You can drive from Pompeii to Positano in an hour. Another option is to do a combination of train and bus. In April, plan for daily highs up to 67°F, and evening lows to 55°F. Finish your sightseeing early on the 10th (Tue) so you can ride a ferry to Anacapri.

Things to do in Positano

Parks Wildlife Nature

Side Trips

Ravello, Il Tempio di Nettuno o Poseidone o di Hera II, Valle delle Ferriere, Castello di Arechi
Find places to stay Apr 8 — 10:
Highlights from your plan
Villa Rufolo ©
Villa Rufolo
Le Ville di Ravello ©
Le Ville di Ravello

2
nights
Anacapri, Island of Capri

Anacapri ©
Anacapri is a comune on the island of Capri, in the Metropolitan City of Naples, Italy. Your day-by-day itinerary now includes I Faraglioni as well as Villa Jovis. On your second day here, take in the dramatic natural features at I Faraglioni, then take an in-depth tour of Villa San Michele, then take some stellar pictures from Monte Solaro Chairlift Seggiovia Monte Solaro, and finally delve into the distant past at Villa Jovis.

To see reviews, more things to do, other places to visit, and more tourist information, read Anacapri online sightseeing planner .

Ride a ferry from Positano to Anacapri in an hour. Expect a daytime high around 67°F in April, and nighttime lows around 55°F. Wrap up your sightseeing on the 12th (Thu) to allow time to travel to Rome.

Things to do in Anacapri

Historic Sites Museums Nature

Side Trip

Capri
Find places to stay Apr 10 — 12:
Highlights from your plan
Villa San Michele ©
Villa San Michele
I Faraglioni
I Faraglioni
Scala Fenicia (Phoenician Steps) ©
Scala Fenicia (Phoenician Steps)

16
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Your list of things to see and do now includes Lapis Niger, Villa Lante, Chiesa di Santa Maria del Popolo, and other attractions. You'll discover tucked-away gems like San Pietro in Vincoli and Cupola di San Pietro. Let the collections at Le Domus Romane di Palazzo Valentini and Musei Capitolini capture your imagination. Venture out of the city with trips to Tivoli (Villa Adriana, Villa d'Este, & more), Parco Archeologico di Ostia Antica (in Ostia Antica) and Giardino di Ninfa (in Cisterna di Latina). And it doesn't end there: contemplate the long history of Basilica Papale San Paolo fuori le Mura, take in the architecture and atmosphere at Santa Maria in Trastevere, indulge your senses at some of the top wineries in the area, and get to know the fascinating history of Piazza Venezia.

To find reviews, ratings, photos, and other tourist information, go to the Rome visit planning website .

Traveling by combination of ferry and train from Anacapri to Rome takes 3.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry, subway, and train. Traveling from Anacapri in April, you can expect nighttime temperatures to be a bit cooler in Rome, with lows of 49°F. Wrap up your sightseeing on the 28th (Sat) to allow time to travel to Pisa.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Vatican City, Tivoli, Orvieto, Eremo della Madonna d'Appari, Labro
Find places to stay Apr 12 — 28:
Highlights from your plan
Cupola di San Pietro ©
Cupola di San Pietro
Parco Archeologico di Ostia Antica ©

2
nights
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Your day-by-day itinerary now includes Costiera di Calafuria, Duomo di Pisa, Battistero, and other attractions you added. On the 29th (Sun), see the vivid underwater world at Costiera di Calafuria, then take in the spiritual surroundings of Battistero, then steep yourself in history at Camposanto, and finally admire the striking features of Duomo di Pisa. Here are some ideas for day two: take in the spiritual surroundings of Chiesa di Santa Maria della Spina, take in the architecture and atmosphere at Basilica romanica di San Piero a Grado, snap pictures at Ponte della Maddalena (detto Ponte del Diavolo), then don't miss a visit to Torre delle Ore, and finally make a trip to Via Fillungo.

To find photos, ratings, where to stay, and tourist information, refer to the Pisa route builder .

You can take a train from Rome to Pisa in 2.5 hours. Other options are to fly; or drive. In April in Pisa, expect temperatures between 65°F during the day and 48°F at night. Finish your sightseeing early on the 30th (Mon) to allow enough time to take a train to Florence.

Things to do in Pisa

Historic Sites Wildlife Parks

Side Trips

Lucca, Costiera di Calafuria, Ponte della Maddalena - Ponte del Diavolo
Find places to stay Apr 28 — 30:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Battistero ©
Battistero
Chiesa di Santa Maria della Spina ©
Chiesa di Santa Maria della Spina

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
You've added Basilica of Santa Croce in Florence, Campanile di Giotto, Palazzo Strozzi, and other attractions to your itinerary. Get some historical perspective at Abbazia di San Miniato al Monte and The Baptistery of St. John. Let the collections at Pitti Palace and Museum of Opera of Saint Maria of Fiore capture your imagination. There's more to do: admire the landmark architecture of Basilica of Santa Maria Novella and contemplate the long history of Loggia dei Lanzi.

For ratings, other places to visit, and other tourist information, use the Florence trip maker website .

Traveling by train from Pisa to Florence takes an hour. Alternatively, you can drive; or take a bus. In April, daytime highs in Florence are 66°F, while nighttime lows are 47°F. Finish up your sightseeing early on the 4th (Fri) so you can catch the train to Milan.

Things to do in Florence

Museums Historic Sites Childrens Museums

Side Trips

San Gimignano 1300, Abbazia di San Galgano
Find places to stay Apr 30 — May 4:
Highlights from your plan
Abbazia di San Galgano ©
Abbazia di San Galgano
Basilica San Miniato al Monte
Basilica San Miniato al Monte
The Baptistery of St. John ©
The Baptistery of St. John

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.
Your day-by-day itinerary now includes Sforzesco Castle, Pinacoteca di Brera, Chiesa di San Maurizio al Monastero Maggiore, and other attractions you added.

To see traveler tips, other places to visit, ratings, and more tourist information, read Milan trip maker .

Traveling by train from Florence to Milan takes 2 hours. Alternatively, you can drive; or take a bus. In May, plan for daily highs up to 73°F, and evening lows to 55°F. Wrap up your sightseeing on the 7th (Mon) early enough to take a train to Venice.

Things to do in Milan

Historic Sites Museums
Find places to stay May 4 — 7:
Highlights from your plan
Piazza di Santa Maria delle Grazie, 2 ©
Pinacoteca di Brera ©
Pinacoteca di Brera

7
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.
You've added Porta della Carta, Isola di Burano, Punta della Dogana, and other attractions to your itinerary. You'll explore the less-touristy side of things at Ponte dei Sospiri and Le Mura. Palazzo dei Diamanti and Castello del Catajo will appeal to museum buffs. The adventure continues: admire the masterpieces at Museo Correr, step into the grandiose world of Ca' d'Oro, steep yourself in history at Chiesa di San Zaccaria, and contemplate the waterfront views at Laguna Veneta.

To find traveler tips, more things to do, photos, and other tourist information, you can read our Venice route app .

Getting from Milan to Venice by train takes about 3 hours. Other options: drive; or do a combination of flight and shuttle. In May, daily temperatures in Venice can reach 72°F, while at night they dip to 55°F. Cap off your sightseeing on the 14th (Mon) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Nature

Side Trips

Ferrara, Castello del Catajo
Find places to stay May 7 — 14:
Highlights from your plan
Scuola Grande di San Rocco ©
Scuola Grande di San Rocco
San Giorgio Maggiore ©
San Giorgio Maggiore
Basilica di Santa Maria della Salute ©

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