18 days in Italy Itinerary

18 days in Italy Itinerary

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Route & dates

18 days in Italy Itinerary

Start: Santiago
Fly:  20​h
1
Como
— 2 nights
Train:  45​min
2
Milan
— 2 nights
Train:  1​h 45​min
3
Genoa
— 2 nights
Train:  1​h 15​min
4
Cinque Terre
— 2 nights
Drive:  2​h 45​min
5
San Gimignano
— 1 night
Drive:  1​h
6
Siena
— 2 nights
Drive:  4​h 45​min
7
Sorrento
— 2 nights
Subway:  45​min
8
Pompeii
— 1 night
Bus:  15​min
9
Naples
— 1 night
Train + Fly:  18​h 45​min
End: Santiago

2
nights
Como

Como ©
Known for its idyllic location on the shores of Lake Como and at the foot of the Alps, Como is one of northern Italy's most popular tourist destinations.
On the 3rd (Sun), take an in-depth tour of Civic Museum of the Risorgimento, get engrossed in the history at Civico Museo Archeologico Paolo Giovio, then look for gifts at Tea World, then get into the urban bustle at Broletto, and finally take in the architecture and atmosphere at Basilica di San Vincenzo in Galliano. On the 4th (Mon), you'll have a packed day of sightseeing: appreciate the extensive heritage of Porta torre di Como, then stroll around Parco Spina verde, then make a trip to Basilica di Agliate, and finally pause for some serene contemplation at Santuary of Our Lady of Miracles.

To find where to stay, traveler tips, photos, and other tourist information, use the Como trip planner.

Santiago, Chile to Como 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 May, daily temperatures in Como can reach 25°C, while at night they dip to 13°C. Cap off your sightseeing on the 4th (Mon) early enough to catch the train to Milan.

Things to do in Como

Historic Sites Museums Shopping

Side Trips

Basilica di Agliate, Basilica di San Vincenzo in Galliano, Santuary of Our Lady of Miracles
Find places to stay May 2 — 4:
Highlights from your plan
Broletto ©
Broletto
Basilica di San Vincenzo in Galliano ©
Civic Museum of the Risorgimento ©
Civic Museum of the Risorgimento

2
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.
Start off your visit on the 5th (Tue): explore the ancient world of Teatro Romano, then take in the architecture and atmosphere at Santa Maria del Carmine, then take an in-depth tour of Museo Teatrale alla Scala, and finally steep yourself in history at Palazzo Clerici. On the 6th (Wed), you'll have a packed day of sightseeing: pause for some serene contemplation at Basilica di San Vittore al Corpo, then examine the collection at Armani Silos, then take in the architecture and atmosphere at Church of San Giorgio al Palazzo, and finally pause for some serene contemplation at Chiesa di Sant'Alessandro in Zebedia.

To find where to stay, other places to visit, reviews, and tourist information, read Milan day trip site .

Traveling by train from Como to Milan takes an hour. Alternatively, you can drive. May in Milan sees daily highs of 26°C and lows of 15°C at night. Cap off your sightseeing on the 6th (Wed) early enough to catch the train to Genoa.

Things to do in Milan

Historic Sites Museums
Find places to stay May 4 — 6:
Highlights from your plan
Teatro Romano ©
Teatro Romano
Basilica di San Vittore al Corpo ©
Basilica di San Vittore al Corpo
Chiesa di Sant'Alessandro in Zebedia ©

2
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.
Start off your visit on the 7th (Thu): take in the spiritual surroundings of Basilica DI Santa Maria Assunta, see the interesting displays at Raccolta Frugone, examine the collection at Musei di Nervi Wolfsoniana, then admire the masterpieces at Musei di Nervi - Galleria d'Arte Moderna GAM, and finally explore the world behind art at Museo Diocesano Chiostro dei Canonici di San Lorenzo. Get ready for a full day of sightseeing on the next day: contemplate in the serene atmosphere at Abbazia di San Siro di Struppa, examine the collection at Museo del Risorgimento Istituto Mazziniano, contemplate in the serene atmosphere at Chiesa di San Filippo Neri, then examine the collection at Palazzo Doria Tursi, then get to know the fascinating history of Via Macelli di Soziglia, and finally contemplate the long history of Chiesa di Santo Stefano.

To find more things to do and other tourist information, read our Genoa trip planner .

Getting from Milan to Genoa by train takes about 2 hours. Other options: drive. In May, plan for daily highs up to 24°C, and evening lows to 17°C. Cap off your sightseeing on the 8th (Fri) early enough to catch the train to Cinque Terre.

Things to do in Genoa

Museums Historic Sites

Side Trip

Basilica DI Santa Maria Assunta
Find places to stay May 6 — 8:
Highlights from your plan

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.
Start off your visit on the 9th (Sat): take in the spiritual surroundings of Chiesa di San Lorenzo, take in the spiritual surroundings of Chiesa Di San Pietro, then appreciate the extensive heritage of Borgo Storico di Corniglia, then explore the historical opulence of Castello Doria, and finally take in the architecture and atmosphere at Santa Margherita di Antiochia Church. Here are some ideas for day two: appreciate the extensive heritage of Groppo, see the interesting displays at Museo Civico Etnografico, then appreciate the extensive heritage of Borgo Storico di Riomaggiore, then take in the architecture and atmosphere at Convento dei Cappuccini e Chiesa di San Francesco, and finally make a trip to Borgo Antico.

To see photos, traveler tips, and more tourist information, use the Cinque Terre tour itinerary planner .

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, Cinque Terre is little chillier at night with lows of 13°C. Cap off your sightseeing on the 10th (Sun) early enough to go by car to San Gimignano.

Things to do in Cinque Terre

Historic Sites Museums

Side Trip

Museo Civico Etnografico
Find places to stay May 8 — 10:
Highlights from your plan
Chiesa di San Lorenzo ©
Chiesa di San Lorenzo
Santa Margherita di Antiochia Church ©
Castello Doria ©
Castello Doria

1
night
San Gimignano

San Gimignano ©
A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Kick off your visit on the 11th (Mon): take in the exciting artwork at Vitalita Cultural Association, view the masterpieces at Oibo Re-Design, take in the spiritual surroundings of Chiesa di San Pietro in Forliano, then pause for some serene contemplation at Santuario Maria SS. Madre della Divina Provvidenza, then contemplate the long history of Porta San Giovanni, and finally view the masterpieces at Art Gallery in Tuscany.

To see ratings, where to stay, reviews, and other tourist information, you can read our San Gimignano trip maker app .

Traveling by car from Cinque Terre to San Gimignano takes 3 hours. Alternatively, you can take a train. In May in San Gimignano, expect temperatures between 25°C during the day and 13°C at night. Wrap up your sightseeing on the 11th (Mon) to allow time to drive to Siena.

Things to do in San Gimignano

Shopping Museums Historic Sites
Find places to stay May 10 — 11:
Highlights from your plan
Oibo Re-Design ©
Oibo Re-Design
Porta San Giovanni ©
Porta San Giovanni

2
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 12th (Tue), don't miss a visit to Abazzia di Torri, contemplate the long history of Loggia della Mercanzia, admire the landmark architecture of Palazzo Salimbeni, get to know the fascinating history of Piazza Salimbeni, then get engrossed in the history at Museo Contrada Priora della Civetta, and finally contemplate the long history of Palazzo Piccolomini. On the next day, examine the collection at Museo dell'Acqua, take in the architecture and atmosphere at Chiesa di S.Agostino, have fun and explore at Museo di Storia Naturale dell'Accademia dei Fisiocritici, contemplate the long history of Porta Romana, then get engrossed in the history at Archivio di Stato, and finally admire the landmark architecture of Palazzo Sansedoni.

For other places to visit, reviews, maps, and other tourist information, use the Siena trip app .

Traveling by car from San Gimignano to Siena takes an hour. Alternatively, you can take a bus; or do a combination of bus and train. In May, daytime highs in Siena are 27°C, while nighttime lows are 13°C. Cap off your sightseeing on the 13th (Wed) early enough to go by car to Sorrento.

Things to do in Siena

Museums Historic Sites Childrens Museums

Side Trip

Abazzia di Torri
Find places to stay May 11 — 13:
Highlights from your plan
Museo Contrada Priora della Civetta ©
Abazzia di Torri ©
Abazzia di Torri
Palazzo Piccolomini ©
Palazzo Piccolomini

2
nights
Sorrento

Sorrento ©
A lovely town easily accessible from almost anywhere in the country, Sorrento overlooks the Bay of Naples and sits right on the Amalfi Drive.
Start off your visit on the 13th (Wed): contemplate in the serene atmosphere at Monastero di San Paolo, take in the spiritual surroundings of Basilica di Sant'Antonino, pause for some serene contemplation at Cattedrale di Sorrento, then take in the spiritual surroundings of Duomo dei San Filippo e Giacomo, and finally admire the verdant scenery at Il Vallone dei Mulini. Here are some ideas for day two: stroll through Baia di Ieranto and then explore the world behind art at Museobottega della Tarsialignea.

To see traveler tips, ratings, more things to do, and more tourist information, refer to the Sorrento trip app .

You can drive from Siena to Sorrento in 5 hours. Alternatively, you can do a combination of train and subway; or do a combination of bus, flight, train, and subway. Traveling from Siena in May, expect a bit warmer with lows of 18°C in Sorrento. Cap off your sightseeing on the 14th (Thu) early enough to take the subway to Pompeii.

Things to do in Sorrento

Historic Sites Parks Beaches

Side Trip

Massa Lubrense
Find places to stay May 13 — 15:
Highlights from your plan
Monastero di San Paolo ©
Monastero di San Paolo
Cattedrale di Sorrento ©
Cattedrale di Sorrento
Il Vallone dei Mulini ©
Il Vallone dei Mulini

1
night
Pompeii

Pompeii ©
Pompeii has been a tourist destination for more than 250 years.
Start off your visit on the 16th (Sat): explore the ancient world of Villa di Giulia Felice, don't miss a visit to Garden of Ship Europa House - Excavations, explore the ancient world of Edificio di Eumachia, admire the landmark architecture of Casa del Cinghiale, then delve into the distant past at Domus Cornelia, and finally explore the ancient world of Tempio di Venere.

To see more things to do, other places to visit, photos, and other tourist information, read our Pompeii trip planner .

Traveling by subway from Sorrento to Pompeii takes an hour. Alternatively, you can drive; or take a bus. May in Pompeii sees daily highs of 27°C and lows of 17°C at night. Cap off your sightseeing on the 16th (Sat) early enough to catcht the bus to Naples.

Things to do in Pompeii

Historic Sites
Find places to stay May 15 — 16:
Highlights from your plan
Villa di Giulia Felice ©
Villa di Giulia Felice
Edificio di Eumachia ©
Edificio di Eumachia
Tempio di Venere ©
Tempio di Venere

1
night
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Start off your visit on the 17th (Sun): contemplate the long history of Acquaquiglia del Pozzaro, get engrossed in the history at Museo delle Torture, then admire the landmark architecture of Chiesa di San Gregorio Armeno, and finally explore the ancient world of Casa di Nettuno e Anfitrite.

For maps, more things to do, ratings, and other tourist information, read our Naples trip builder app .

Naples is just a short distance from Pompeii. In May in Naples, expect temperatures between 27°C during the day and 17°C at night. Finish up your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Naples

Historic Sites Museums

Side Trip

Casa di Nettuno e Anfitrite
Find places to stay May 16 — 17:
Highlights from your plan
Acquaquiglia del Pozzaro ©
Acquaquiglia del Pozzaro
Casa di Nettuno e Anfitrite ©
Casa di Nettuno e Anfitrite
Museo delle Torture ©
Museo delle Torture

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