58 days in Italy Itinerary

58 days in Italy Itinerary

Created using Inspirock Italy trip planner

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Route & dates

58 days in Italy Itinerary

Start: Colombo
Fly:  17​h 15​min
1
Catania, Sicily
— 1 day
Fly + Drive:  4​h 45​min
2
Tramonti
— 2 nights
Drive:  1​h 15​min
3
Positano
— 7 nights
bus:  1​h 15​min
4
Naples
— 5 nights
train:  1​h 15​min
5
Rome
— 10 nights
Drive:  2​h 15​min
6
Assisi
— 8 nights
Drive:  2​h 15​min
7
Florence
— 9 nights
train:  1​h 45​min
8
Milan
— 5 nights
train:  2​h 30​min
9
Venice
— 9 nights
Fly:  16​h 15​min
End: Colombo

1
day
Catania, Sicily

Catania ©
The landscape surrounding Catania, a medieval city on Sicily's eastern coast, is dominated by Mount Etna, the tallest active volcano in Europe.
On the 3rd (Sat), get outside with EtnaExcursion.it.

To see other places to visit, reviews, where to stay, and other tourist information, use the Catania itinerary planner.

Colombo, Sri Lanka to Catania is an approximately 17.5-hour flight. Traveling from Colombo to Catania, you'll gain 4 hours due to the time zone difference. On the 3rd (Sat), wrap the sightseeing up by early afternoon so you can travel to Tramonti.

Things to do in Catania

Wildlife Tours Outdoors

Side Trip

EtnaExcursion.it
Find places to stay Nov 3 — 4:
Highlights from your plan
EtnaExcursion.it ©
EtnaExcursion.it

2
nights
Tramonti

Tramonti ©
On the 4th (Sun), appreciate the extensive heritage of Centro Storico Ravello, steep yourself in history at Duomo di Ravello, then steep yourself in history at Villa Rufolo, and finally contemplate the long history of Villa Cimbrone Gardens. Keep things going the next day: get outside with Monte Finestra, then learn about winemaking at Le Vigne di Raito, then make a trip to Parrocchia di Santa Maria a Mare, and finally sample the fine beverages at Liquorificio Mansi Carlo.

To find traveler tips, maps, more things to do, and tourist information, use the Tramonti trip planner .

The Route module can help you plan travel from Catania to Tramonti. Expect a daytime high around 21°C in November, and nighttime lows around 17°C. Cap off your sightseeing on the 5th (Mon) early enough to travel to Positano.

Things to do in Tramonti

Historic Sites Outdoors Parks

Side Trips

Ravello, Liquorificio Mansi Carlo, Parrocchia di Santa Maria a Mare, Le Vigne di Raito
Find places to stay Nov 3 — 5:
Highlights from your plan
Le Vigne di Raito ©
Le Vigne di Raito
Duomo di Ravello ©
Duomo di Ravello
Villa Rufolo ©
Villa Rufolo

7
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.
Get out of town with these interesting Positano side-trips: Amalfi (Wine Tours & Tastings, Duomo di Sant'Andrea, & more). Next up on the itinerary: enjoy the sand and surf at Fornillo, don't miss a visit to Parocchia di San Luca Evangelista, have fun at Tennis Al Settimo Piano, and head off the coast to Li Galli.

Start your trip to Positano by creating a personalized itinerary on Inspirock.

You can drive from Tramonti to Positano in 1.5 hours. Expect a daytime high around 20°C in November, and nighttime lows around 15°C. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Naples.

Things to do in Positano

Outdoors Parks Nature

Side Trips

Amalfi, Praiano, Cantine Marisa Cuomo
Find places to stay Nov 5 — 12:
Highlights from your plan
Fornillo ©
Fornillo
Duomo di Sant'Andrea ©
Duomo di Sant'Andrea
Valle dei Mulini ©
Valle dei Mulini

5
nights
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Get out of town with these interesting Naples side-trips: Salerno (Chiesa di San Giorgio, Cappella Santa Maria Delle Grazie Salerno, & more) and Villa dei Misteri (in Pompeii). Dedicate the 14th (Wed) to wine at some of the top wineries in the area. There's much more to do: steep yourself in history at Gli Scavi Archeologici di Pompei, make a trip to Via San Gregorio Armeno, examine the collection at National Archaeological Museum of Naples, and pause for some serene contemplation at Duomo di Napoli.

For maps, ratings, where to stay, and tourist information, go to the Naples trip itinerary builder tool .

You can drive from Positano to Naples in 1.5 hours. Other options are to do a combination of bus and subway; or ride a ferry. Traveling from Positano in November, plan for little chillier nights in Naples, with lows around 11°C. Finish your sightseeing early on the 17th (Sat) so you can take a train to Rome.

Things to do in Naples

Tours Historic Sites Museums

Side Trips

Salerno, Pompeii, Parco Acheologico di Ercolano
Find places to stay Nov 12 — 17:
Highlights from your plan
Wine Tours & Tastings
Pompeii Archaeological Park ©
Pompeii Archaeological Park

10
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Get out of town with these interesting Rome side-trips: Tivoli (Villa Adriana & Villa d'Este). The adventure continues: explore the ancient world of Colosseum, explore the world behind art at Vatican Museums, admire the landmark architecture of Pantheon, and don't miss a visit to Spanish Steps.

To see reviews, ratings, and more tourist information, refer to the Rome attractions planning tool .

Traveling by train from Naples to Rome takes 1.5 hours. Alternatively, you can drive; or take a bus. In November, plan for daily highs up to 20°C, and evening lows to 9°C. Finish your sightseeing early on the 27th (Tue) so you can drive to Assisi.

Things to do in Rome

Historic Sites Museums Tours

Side Trips

Vatican City, Tivoli
Find places to stay Nov 17 — 27:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

8
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
You'll find plenty of places to visit near Assisi: Scoglio della Preghiera (in Cascia), Vineria del Carmine (in La Bruna) and Wild Foods Italy (in Montefalco). There's still lots to do: pause for some serene contemplation at Basilica inferiore di San Francesco d'Assisi, contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli, stop by Art Leather, and contemplate the long history of Eremo delle Carceri.

For where to stay, maps, reviews, and more tourist information, you can read our Assisi itinerary planning site .

Traveling by car from Rome to Assisi takes 2.5 hours. Alternatively, you can take a train; or take a bus. Expect a bit cooler weather when traveling from Rome in November: highs in Assisi hover around 17°C, while lows dip to 7°C. Cap off your sightseeing on the 5th (Wed) early enough to go by car to Florence.

Things to do in Assisi

Historic Sites Shopping Parks

Side Trips

Wild Foods Italy, Scoglio della Preghiera, Piana di Castelluccio di Norcia, Vineria del Carmine
Find places to stay Nov 27 — Dec 5:
Highlights from your plan
Vineria del Carmine ©
Vineria del Carmine
Eremo delle Carceri ©
Eremo delle Carceri

9
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore the numerous day-trip ideas around Florence: Torre di Pisa (in Pisa), Siena (Siena Cathedral, Piazza del Campo, & more) and Guardastelle Vineyard (in San Gimignano). Dedicate the 10th (Mon) to wine at some of the top wineries in the area. The adventure continues: admire the masterpieces at Uffizi Galleries, take in the views from Ponte Vecchio, take in the spiritual surroundings of The Baptistery of St. John, and see the interesting displays at Galleria dell'Accademia.

For more things to do, reviews, other places to visit, and tourist information, refer to the Florence sightseeing planner .

You can drive from Assisi to Florence in 2.5 hours. Other options are to take a train; or take a bus. In December, plan for daily highs up to 15°C, and evening lows to 4°C. Finish your sightseeing early on the 14th (Fri) to allow enough time to take a train to Milan.

Things to do in Florence

Museums Historic Sites Tours

Side Trips

Siena, Leaning Tower of Pisa, Guardastelle Vineyard
Find places to stay Dec 5 — 14:
Highlights from your plan
Food Tours
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

5
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.
Venture out of the city with trips to Turati Centro Nautico Lario (in Argegno), Villa del Balbianello (in Tremezzina) and Como (L'Isola Che Non C'e', Tea World, & more). Spend the 19th (Wed) on two wheels at Anything But Work. The adventure continues: take in the architecture and atmosphere at Duomo di Milano, explore the world behind art at Pinacoteca Ambrosiana, admire the striking features of Galleria Vittorio Emanuele II, and stroll the grounds of Monumental Cemetery.

To see reviews, traveler tips, other places to visit, and other tourist information, refer to the Milan trip itinerary builder app .

You can take a train from Florence to Milan in 2 hours. Alternatively, you can drive; or take a bus. Traveling from Florence in December, expect Milan to be a bit cooler, temps between 9°C and 1°C. Finish your sightseeing early on the 19th (Wed) so you can take a train to Venice.

Things to do in Milan

Outdoors Historic Sites Trails

Side Trips

Como, Anything But Work, Villa del Balbianello, Turati Centro Nautico Lario
Find places to stay Dec 14 — 19:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

9
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.
Venture out of the city with trips to Padua (Centro Storico, Basilica di Sant’Antonio, & more). And it doesn't end there: explore the activities along Canal Grande, don't miss a visit to St. Mark's Square, explore the galleries of Peggy Guggenheim Collection, and admire the masterpieces at Gallerie dell'Accademia.

For more things to do, where to stay, and tourist information, you can read our Venice trip planner.

Traveling by train from Milan to Venice takes 2.5 hours. Alternatively, you can drive; or take a bus. In December, plan for daily highs up to 11°C, and evening lows to 1°C. Cap off your sightseeing on the 28th (Fri) early enough to travel back home.

Things to do in Venice

Historic Sites Museums Tours

Side Trip

Padua
Find places to stay Dec 19 — 28:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Doge's Palace ©
Doge's Palace

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