15 days in Italy Itinerary

15 days in Italy Itinerary

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Route & dates

15 days in Italy Itinerary

Start: Chicago
Fly:  15​h 45​min
1
Palermo, Sicily
— 2 nights
Drive:  3​h
2
Syracuse, Sicily
— 2 nights
+3
Train + Foot + Bus + Fly:  3​h 45​min
3
Lampedusa
— 1 night
Fly + Train:  6​h 15​min
4
Assisi
— 3 nights
Drive + Ferry:  4​h 45​min
5
Capri, Island of Capri
— 1 night
Drive:  2​h 15​min
6
Naples
— 4 nights
Train + Fly:  13​h 45​min
End: Chicago

2
nights
Palermo, Sicily

Palermo ©
The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
Cefalu Coast and Duomo di Monreale are good opportunities to explore the local culture. Popular historic sites such as Santa Maria dell'Ammiraglio and Norman Palace are in your itinerary. Venture out of the city with trips to Riserva Naturale Dello Zingaro (in Castellammare del Golfo) and Duomo di Cefalu (in Cefalu). There's more to do: don't miss a visit to Quattro Canti.

To see more things to do, maps, where to stay, and more tourist information, read our Palermo journey planner .

Chicago, USA to Palermo is an approximately 16-hour flight. You can also do a combination of flight and bus; or do a combination of train and flight. Due to the time zone difference, you'll lose 7 hours traveling from Chicago to Palermo. Finish your sightseeing early on the 27th (Sat) to allow enough time to drive to Syracuse.

Things to do in Palermo

Historic Sites Wildlife Parks

Side Trips

Cefalu, Riserva Naturale Dello Zingaro, Duomo di Monreale
Highlights from your plan
Cefalu Coast ©
Cefalu Coast
Santa Maria dell'Ammiraglio ©
Santa Maria dell'Ammiraglio
Duomo di Monreale ©
Duomo di Monreale

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.
Start off your visit on the 28th (Sun): take an in-depth tour of Museo Archeologico Regionale Paolo Orsi, appreciate the extensive heritage of Centro Storico, then pause for some serene contemplation at St. Nicholas Cathedral, and finally take in the architecture and atmosphere at Duomo di Siracusa. Keep things going the next day: explore the fascinating underground world of Cavagrande del Cassibile, then pause for some serene contemplation at Monastero del San salvatore, then look for all kinds of wild species at Riserva Naturale Orientata Oasi faunistica di Vendicari, and finally explore the fascinating underground world of Ear of Dionysius (Orecchio di Dionisio).

For ratings, traveler tips, where to stay, and tourist information, refer to the Syracuse trip itinerary planning site .

Traveling by car from Palermo to Syracuse takes 3 hours. Alternatively, you can take a bus; or take a train. Finish up your sightseeing early on the 29th (Mon) so you can travel to Lampedusa.

Things to do in Syracuse

Historic Sites Parks Nature

Side Trips

Noto, Cavagrande del Cassibile
Highlights from your plan
St. Nicholas Cathedral ©
St. Nicholas Cathedral
Cavagrande del Cassibile ©
Cavagrande del Cassibile

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 30th (Tue): look for all kinds of wild species at Centro di Recupero Tartarughe e Fauna Selvatica WWF, stroll through Cala Pulcino, and then stroll through Spiaggia dei Conigli.

To see traveler tips, where to stay, photos, and tourist information, use the Lampedusa trip planning tool .

Traveling by combination of train and flight from Syracuse to Lampedusa takes 4 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. In June, daytime highs in Lampedusa are 76°F, while nighttime lows are 69°F. Finish your sightseeing early on the 30th (Tue) so you can travel to Assisi.

Things to do in Lampedusa

Parks Outdoors Beaches
Highlights from your plan
Cala Pulcino ©
Cala Pulcino
Spiaggia dei Conigli ©
Spiaggia dei Conigli

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Step out of the city life by going to Cascata delle Marmore and Grotte di Frasassi. You'll explore the less-touristy side of things at Pozzo di San Patrizio and Cattedrale di Santa Maria Assunta Spoleto. Venture out of the city with trips to Duomo di Orvieto (in Orvieto) and Rocca Paolina (in Perugia). And it doesn't end there: examine the collection at Museo della Porziuncola, contemplate in the serene atmosphere at Eremo delle Carceri, take in the architecture and atmosphere at Basilica di Santa Maria degli Angeli - Porziuncola, and steep yourself in history at San Damiano.

To see reviews, traveler tips, other places to visit, and other tourist information, use the Assisi trip planner.

Do a combination of flight and train from Lampedusa to Assisi in 6.5 hours. Alternatively, you can fly; or do a combination of ferry and car. Traveling from Lampedusa in June, you will find days in Assisi are somewhat warmer (82°F), and nights are little chillier (60°F). Finish up your sightseeing early on the 3rd (Fri) so you can travel to Capri.

Things to do in Assisi

Historic Sites Nature Parks

Side Trips

Orvieto, Cattedrale di Santa Maria Assunta Spoleto, Grotte di Frasassi, Rocca Paolina, Cascata delle Marmore
Highlights from your plan
Basilica di Santa Chiara ©
Basilica di Santa Chiara
San Damiano ©
San Damiano

1
night
Capri, Island of Capri

Capri ©
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Kick off your visit on the 4th (Sat): take in the architecture and atmosphere at Chiesa di Santa Sofia, explore the striking landscape at I Faraglioni, don't miss a visit to Giardini di Augusto, then explore the galleries of Villa San Michele, and finally Head underground at Blue Grotto.

To see more things to do, traveler tips, photos, and tourist information, you can read our Capri road trip planning tool .

Getting from Assisi to Capri by combination of car and ferry takes about 5 hours. Other options: do a combination of train and ferry; or do a combination of train, flight, and ferry. Traveling from Assisi in July, expect somewhat warmer with lows of 72°F in Capri. Finish your sightseeing early on the 4th (Sat) to allow enough time to drive to Naples.

Things to do in Capri

Parks Historic Sites Nature

Side Trip

Anacapri
Highlights from your plan
Villa San Michele ©
Villa San Michele
Chiesa di Santa Sofia ©
Chiesa di Santa Sofia
Blue Grotto ©
Blue Grotto

4
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. You'll explore the less-touristy side of things at Monte Cassino and Duomo di Salerno. Castello Aragonese d'Ischia and Underground Naples will appeal to history buffs. Explore Naples' surroundings by going to Vesuvio National Park (in Ottaviano) and Paestum Ruins (in Paestum). The adventure continues: contemplate the long history of Galleria Borbonica, delve into the distant past at Parco Acheologico di Ercolano, appreciate the extensive heritage of Via Caracciolo e Lungomare di Napoli, and don't miss a visit to Via San Gregorio Armeno.

To find reviews, ratings, traveler tips, and more tourist information, go to the Naples journey builder app .

Drive from Capri to Naples in 2.5 hours. In July, plan for daily highs up to 87°F, and evening lows to 70°F. Finish your sightseeing early on the 8th (Wed) so you can travel back home.

Things to do in Naples

Historic Sites Museums Nature

Side Trips

Paestum Ruins, Duomo di Salerno, Vesuvio National Park, Castello Aragonese d'Ischia, Monte Cassino
Highlights from your plan
Monte Cassino ©
Monte Cassino
Duomo di Salerno ©
Duomo di Salerno
Castello Aragonese d'Ischia ©
Castello Aragonese d'Ischia

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