20 days in Italy Itinerary

20 days in Italy Itinerary

Created using Inspirock Italy trip planner

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Route & dates

20 days in Italy Itinerary

Start: Kelowna
Fly:  18​h
1
Milan
— 1 night
Fly:  3​h 30​min
2
Lampedusa
— 1 night
+3
Fly + bus + foot + train:  3​h 45​min
3
Syracuse, Sicily
— 2 nights
+3
train + foot + bus + Fly:  5​h 30​min
4
Rome
— 2 nights
5
Naples
— 3 nights
train:  2​h 45​min
6
Florence
— 3 nights
7
Venice
— 5 nights
Fly:  16​h 15​min
End: Kelowna

1
night
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.
You've now added La Scala Opera to your itinerary. On the 2nd (Wed), take in the architecture and atmosphere at Duomo di Milano and then get lost in a book at Pinacoteca Ambrosiana. Keep things going the next day: see the grandeur of opera at La Scala Opera and then explore the different monuments and memorials at Monumental Cemetery.

To see where to stay, other places to visit, ratings, and other tourist information, refer to the Milan sightseeing planner .

Kelowna, Canada to Milan is an approximately 18-hour flight. You can also do a combination of bus and flight. Traveling from Kelowna to Milan, you'll lose 9 hours due to the time zone difference. In December, plan for daily highs up to 9°C, and evening lows to 1°C. Finish your sightseeing early on the 3rd (Thu) to allow enough time to travel to Lampedusa.

Things to do in Milan

Historic Sites Nightlife Museums
Find places to stay Dec 2 — 3:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Monumental Cemetery ©
Monumental Cemetery
Teatro Alla Scala ©
Teatro Alla Scala

1
night
Lampedusa

Lampedusa ©
Italy's southernmost territory, Lampedusa, is known for its turquoise waters, white-sand beaches, and island charm.
Kick off your visit on the 4th (Fri): tour the pleasant surroundings at Spiaggia dei Conigli, then enjoy the sand and surf at Cala Pulcino, and then don't miss a visit to Cala Calandra.

To see traveler tips, more things to do, other places to visit, and more tourist information, read Lampedusa trip itinerary app .

You can fly from Milan to Lampedusa in 3.5 hours. Alternatively, you can do a combination of train, bus, and ferry; or do a combination of car and ferry. Traveling from Milan in December, you will find days in Lampedusa are a bit warmer (20°C), and nights are much hotter (17°C). Finish up your sightseeing early on the 4th (Fri) so you can travel to Syracuse.

Things to do in Lampedusa

Parks Outdoors Beaches
Find places to stay Dec 3 — 4:
Highlights from your plan
Spiaggia dei Conigli ©
Spiaggia dei Conigli
Cala Pulcino ©
Cala Pulcino
Cala Calandra ©
Cala Calandra

2
nights
Syracuse, Sicily

Syracuse ©
Philosopher Cicero once described Syracuse as "the greatest Greek city and the most beautiful of them all." A powerful city-state of ancient Greece, Syracuse now is the capital of the eponymous Italian province on the eastern coast of Sicily.
Kick off your visit on the 5th (Sat): get to know the fascinating history of Centro Storico, then steep yourself in history at Chiesa Rupestre del Crocifisso, then take in the architecture and atmosphere at Chiesa Madre Santa Maria La Cava e Sant'Alfio, and finally take in the architecture and atmosphere at Syracuse Cathedral. On the 6th (Sun), you'll have a packed day of sightseeing: Head underground at Ear of Dionysius (Orecchio di Dionisio), appreciate the extensive heritage of Corso Vittorio Emanuele III, then contemplate in the serene atmosphere at Chiesa di San Carlo Borromeo, and finally explore the activities along Riserva Naturale Orientata Oasi faunistica di Vendicari.

Planning Syracuse trip won't be overwheling when you use's Insprock itinerary maker.

You can do a combination of flight and train from Lampedusa to Syracuse in 4 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Cap off your sightseeing on the 6th (Sun) early enough to travel to Rome.

Things to do in Syracuse

Historic Sites Parks Wildlife

Side Trips

Noto, Lentini
Find places to stay Dec 4 — 6:
Highlights from your plan
Syracuse Cathedral ©
Syracuse Cathedral
Centro Storico ©
Centro Storico

2
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Visit Palatine Hill and Colosseum for their historical value. Get some cultural insight at Piazza Navona and Pantheon. There's lots more to do: contemplate in the serene atmosphere at Vatican Museums, pause for some serene contemplation at Santa Maria in Trastevere, wander the streets of Trastevere, and admire the masterpieces at Galleria Borghese.

For photos and tourist information, you can read our Rome journey planner.

Getting from Syracuse to Rome by combination of train and flight takes about 5.5 hours. Other options: do a combination of car and ferry; or do a combination of train and ferry. In December in Rome, expect temperatures between 16°C during the day and 4°C at night. Finish your sightseeing early on the 9th (Wed) to allow enough time to take a train to Naples.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Find places to stay Dec 6 — 9:
Highlights from your plan
St. Peter's Basilica ©
St. Peter's Basilica
Pantheon ©
Pantheon
Colosseum ©
Colosseum

3
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Gli Scavi Archeologici di Pompei and Ruins of Herculaneum will appeal to history buffs. Get a sense of the local culture at Galleria Borbonica and Underground Naples. Explore the numerous day-trip ideas around Naples: Ravello (Villa Cimbrone Gardens & Villa Rufolo) and Duomo di Sant'Andrea (in Amalfi). Next up on the itinerary: appreciate the extensive heritage of Via Caracciolo e Lungomare di Napoli, take in the architecture and atmosphere at Cloister of Santa Chiara, contemplate the long history of Museo Cappella Sansevero, and explore the ancient world of Catacombe di San Gennaro.

To see other places to visit, reviews, photos, and other tourist information, refer to the Naples trip itinerary planning website .

Getting from Rome to Naples by train takes about 1.5 hours. Other options: drive; or take a bus. In December, daytime highs in Naples are 17°C, while nighttime lows are 6°C. Wrap up your sightseeing on the 12th (Sat) to allow time to take a train to Florence.

Things to do in Naples

Historic Sites Museums Parks

Side Trips

Ravello, Duomo di Sant'Andrea, Pompeii Archaeological Park, Parco Acheologico di Ercolano
Find places to stay Dec 9 — 12:
Highlights from your plan
Parco Acheologico di Ercolano ©
Parco Acheologico di Ercolano
Galleria Borbonica ©
Galleria Borbonica
Underground Naples ©
Underground Naples

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Deepen your sense of the past at sights like Cathedral of Santa Maria del Fiore and Centro Storico. Discover out-of-the-way places like Historic Centre of San Gimignano and Basilica San Miniato al Monte. The adventure continues: explore the world behind art at Uffizi Galleries, browse the exhibits of Basilica di San Lorenzo, get to know the fascinating history of Piazza del Duomo, and examine the collection at Academy Of Florence Art Gallery.

To see photos, reviews, where to stay, and more tourist information, read our Florence route planner .

Getting from Naples to Florence by train takes about 3 hours. Other options: do a combination of train and flight; or drive. In December in Florence, expect temperatures between 15°C during the day and 4°C at night. Finish up your sightseeing early on the 15th (Tue) so you can catch the train to Venice.

Things to do in Florence

Historic Sites Museums

Side Trip

Historic Centre of San Gimignano
Find places to stay Dec 12 — 15:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi

5
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.
Basilica di San Marco and Scrovegni Chapel are good opportunities to explore the local culture. Discover out-of-the-way places like Basilica di Sant’Antonio and Cannaregio. There's lots more to do: contemplate the waterfront views at Canal Grande, admire the striking features of Doge's Palace, take in the spiritual surroundings of Basilica Santa Maria Gloriosa dei Frari, and admire the masterpieces at Gallerie dell'Accademia.

For maps, reviews, ratings, and more tourist information, use the Venice trip maker website .

You can take a train from Florence to Venice in 2.5 hours. Alternatively, you can drive; or take a bus. Expect a bit cooler temperatures when traveling from Florence in December; daily highs in Venice reach 11°C and lows reach 1°C. Cap off your sightseeing on the 20th (Sun) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay Dec 15 — 20:
Highlights from your plan
Doge's Palace ©
Doge's Palace
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

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