25 days in Italy Itinerary

25 days in Italy Itinerary

Created using Inspirock Italy travel route planner

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Route & dates

25 days in Italy Itinerary

Start: Sao Paulo
Fly:  16​h
1
Milan
— 1 night
train:  2​h 30​min
2
Venice
— 4 nights
train:  2​h 15​min
3
Florence
— 4 nights
Drive:  2​h 15​min
4
Assisi
— 2 nights
Drive:  4​h 30​min
5
Ravello
— 4 nights
Drive:  1​h 15​min
6
Naples
— 4 nights
train:  1​h 15​min
7
Rome
— 4 nights
+2
Fly + foot + bus:  15​h
End: Sao Paulo

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.
Kick off your visit on the 6th (Tue): explore the historical opulence of Castello Sforzesco. On your second day here, stroll the grounds of Monumental Cemetery, get lost in a book at Pinacoteca Ambrosiana, then take in the spiritual surroundings of Duomo di Milano, and finally admire the striking features of Galleria Vittorio Emanuele II.

To see other places to visit, reviews, where to stay, and tourist information, use the Milan travel route builder .

Sao Paulo, Brazil to Milan is an approximately 16-hour flight. You can also do a combination of flight and train; or do a combination of bus and flight. The time zone changes from Brasilia Time to Central European Time, which is usually a 4 hour difference. Traveling from Sao Paulo in October, things will get slightly colder in Milan: highs are around 21°C and lows about 13°C. Wrap up your sightseeing on the 7th (Wed) to allow time to take a train to Venice.

Things to do in Milan

Historic Sites Museums Shopping
Find places to stay Oct 6 — 7:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

4
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'll find plenty of places to visit near Venice: Arena di Verona (in Verona) and Scrovegni Chapel (in Padua). There's still lots to do: contemplate the waterfront views at Canal Grande, take in the views from Ponte dei Sospiri, explore the world behind art at Gallerie dell'Accademia, and explore the galleries of Peggy Guggenheim Collection.

To find ratings, other places to visit, traveler tips, and other tourist information, you can read our Venice day trip website .

Traveling by train from Milan to Venice takes 2.5 hours. Alternatively, you can drive; or do a combination of flight and train. Expect a daytime high around 22°C in October, and nighttime lows around 12°C. Finish up your sightseeing early on the 11th (Sun) so you can catch the train to Florence.

Things to do in Venice

Historic Sites Museums Parks

Side Trips

Scrovegni Chapel, Arena di Verona
Find places to stay Oct 7 — 11:
Highlights from your plan
Canal Grande ©
Canal Grande
Basilica di San Marco
Basilica di San Marco
Piazza San Marco ©
Piazza San Marco

4
nights
Florence

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Explore Florence's surroundings by going to Wine Tours & Tastings (in Siena) and Leaning Tower of Pisa (in Pisa). The adventure continues: explore the world behind art at Gallerie Degli Uffizi, enjoy breathtaking views from Campanile di Giotto, get great views at Piazzale Michelangelo, and see the interesting displays at Pitti Palace.

For maps, more things to do, ratings, and other tourist information, read our Florence sightseeing planner .

Traveling by train from Venice to Florence takes 2.5 hours. Alternatively, you can drive; or take a bus. In October, plan for daily highs up to 25°C, and evening lows to 14°C. Finish up your sightseeing early on the 15th (Thu) so you can go by car to Assisi.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Leaning Tower of Pisa, Wine Tours & Tastings
Find places to stay Oct 11 — 15:
Highlights from your plan
Wine Tours & Tastings
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

2
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Kick off your visit on the 16th (Fri): step into the grandiose world of Rocca Maggiore, contemplate the long history of Eremo delle Carceri, stroll around Mount Subasio, then learn about winemaking at Tili Vini Societa Agricola, then examine the collection at Museo della Porziuncola, and finally learn about winemaking at Azienda Agraria Saio. Get ready for a full day of sightseeing on the next day: take in the spiritual surroundings of Cripta di San Francesco, do a tasting at Bibenda Assisi, appreciate the extensive heritage of Piazza Superiore di San Francesco, then pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then get to know the fascinating history of Centro Storico, and finally take in the spiritual surroundings of San Damiano.

For where to stay, photos, reviews, and other tourist information, go to the Assisi road trip site .

You can drive from Florence to Assisi in 2.5 hours. Another option is to take a train. In October, daily temperatures in Assisi can reach 24°C, while at night they dip to 12°C. Finish up your sightseeing early on the 17th (Sat) so you can go by car to Ravello.

Things to do in Assisi

Historic Sites Wineries Parks
Find places to stay Oct 15 — 17:
Highlights from your plan
Tili Vini Societa Agricola ©
Tili Vini Societa Agricola
Eremo delle Carceri ©
Eremo delle Carceri

4
nights
Ravello

Ravello ©
You'll find plenty of places to visit near Ravello: I Suoni degli Dei - Pelagos (in Praiano), Monte Finestra (in Tramonti) and Positano (Fornillo, Il Sentiero Degli Dei, & more).

To find more things to do, where to stay, photos, and tourist information, you can read our Ravello tour builder site .

You can drive from Assisi to Ravello in 4.5 hours. Other options are to take a train; or do a combination of train and bus. Traveling from Assisi in October, expect a bit warmer with lows of 20°C in Ravello. Finish your sightseeing early on the 21st (Wed) to allow enough time to drive to Naples.

Things to do in Ravello

Outdoors Parks Beaches

Side Trips

Positano, Amalfi, Praiano, Monte Finestra, Liquorificio Mansi Carlo
Find places to stay Oct 17 — 21:
Highlights from your plan
Fornillo ©
Fornillo
Il Sentiero Degli Dei ©
Il Sentiero Degli Dei
Duomo di Ravello ©
Duomo di Ravello

4
nights
Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Explore Naples' surroundings by going to Cilento (in Salerno), Le Vigne di Raito (in Vietri sul Mare) and Wine Tours & Tastings (in Amalfi). And it doesn't end there: steep yourself in history at Pompeii Archaeological Park, get some thrills on the water with a speed boat tour, cast your line with a fishing tour, and explore the ancient world of Teatro Grande.

To see ratings, maps, reviews, and tourist information, use the Naples online trip planner .

You can drive from Ravello to Naples in 1.5 hours. Alternatively, you can do a combination of taxi and subway; or take a bus. Traveling from Ravello in October, expect slightly colder with lows of 17°C in Naples. Finish up your sightseeing early on the 25th (Sun) so you can catch the train to Rome.

Things to do in Naples

Tours Outdoors Wildlife

Side Trips

Pompeii, Fishing Charters & Tours, Speed Boats Tours, Le Vigne di Raito, Cilento
Find places to stay Oct 21 — 25:
Highlights from your plan
Wine Tours & Tastings
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Le Vigne di Raito ©
Le Vigne di Raito

4
nights
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Rome is known for historic sites, nightlife, museums, classes, and shopping. Your plan includes some of its best attractions: contemplate the long history of Colosseum, explore the world behind art at Vatican Museums, explore the ancient world of Palatine Hill, and don't miss a visit to Roman Forum.

For more things to do, where to stay, reviews, and tourist information, read our Rome day trip planning site .

Take a train from Naples to Rome in 1.5 hours. Alternatively, you can drive; or take a bus. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Wrap up your sightseeing by early afternoon on the 29th (Thu) to allow enough time to travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Oct 25 — 29:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

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