33 days in Italy Itinerary

33 days in Italy Itinerary

Created using Inspirock Italy Trip Planner

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Route & dates

33 days in Italy Itinerary

Start: Montevideo
Fly:  22​h 45​min
1
Rome
— 1 night
train:  1​h 45​min
2
Florence
— 12 nights
train:  1​h 45​min
3
Milan
— 7 nights
train:  3​h
4
Rome
— 10 nights
Fly:  22​h 45​min
End: Montevideo

1
night
Rome

Rome ©
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
On the 8th (Sun), admire the local landmark of Trevi Fountain, admire the striking features of Pantheon, then get to know the fascinating history of Piazza Navona, then pause for some serene contemplation at Basilica di San Pietro, and finally contemplate the long history of Colosseum.

To see where to stay, reviews, maps, and other tourist information, read our Rome vacation builder.

Montevideo, Uruguay to Rome is an approximately 23-hour flight. Traveling from Montevideo to Rome, you'll lose 4 hours due to the time zone difference. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Wrap up your sightseeing on the 9th (Mon) to allow time to take a train to Florence.

Things to do in Rome

Historic Sites

Side Trip

St. Peter's Basilica
Find places to stay Oct 8 — 9:
Highlights from your plan
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica
Colosseum ©
Colosseum

12
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Let the collections at Pitti Palace and Galleria dell'Accademia capture your imagination. Get a sense of the local culture at Cathedral of Santa Maria del Fiore and Siena Cathedral. Venture out of the city with trips to Torre di Pisa (in Pisa), Siena (Palazzo Pubblico and Museo Civico, Piazza del Campo, & more) and Castello del Trebbio (in Santa Brigida). And it doesn't end there: see the interesting displays at Uffizi Gallery, appreciate the extensive heritage of Piazza della Signoria, get a sense of history and politics at Palazzo Vecchio, and snap pictures at Ponte Vecchio.

To find traveler tips, other places to visit, more things to do, and other tourist information, you can read our Florence itinerary planner.

You can take a train from Rome to Florence in 2 hours. Alternatively, you can drive; or fly. In October, daily temperatures in Florence can reach 25°C, while at night they dip to 15°C. Finish your sightseeing early on the 21st (Sat) so you can take a train to Milan.

Things to do in Florence

Historic Sites Museums Tours

Side Trips

Siena, San Gimignano, Castello del Trebbio, Castello di Verrazzano, Leaning Tower of Pisa
Find places to stay Oct 9 — 21:
Highlights from your plan
Piazzale Michelangelo ©
Piazzale Michelangelo
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

7
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.
Your inner history buff will appreciate Duomo di Milano and Greenway del Lago di Como. You'll explore and learn at Villa Carlotta and i Giardini di Villa Melzi. Get out of town with these interesting Milan side-trips: Como (Basilica of Sant'Abbondio, Tea World, & more), Castello di Corenno Plinio (in Dervio) and Museo Etnografico E Naturalistico Val Sanagra (in Grandola ed Uniti). There's still lots to do: admire the natural beauty at Villa del Balbianello, see the interesting displays at Museo del Ciclismo - Madonna del Ghisallo, admire the masterpieces at Pinacoteca Ambrosiana, and take in the architecture and atmosphere at Basilica di San Giacomo.

To find photos, other places to visit, reviews, and other tourist information, you can read our Milan trip generator.

You can take a train from Florence to Milan in 2 hours. Other options are to drive; or take a bus. Traveling from Florence in October, expect nights in Milan to be about the same, around 13°C, while days are little chillier, around 21°C. Cap off your sightseeing on the 28th (Sat) early enough to catch the train to Rome.

Things to do in Milan

Historic Sites Museums Parks

Side Trips

Como, Bellagio, Tremezzina, La Citta Alta, Museo Etnografico E Naturalistico Val Sanagra
Find places to stay Oct 21 — 28:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Greenway del Lago di Como ©
Greenway del Lago di Como
Castello Sforzesco ©
Castello Sforzesco

10
nights
Rome

Rome ©
You'll explore and learn at Museo Nazionale Etrusco di Villa Giulia and Pamphili Palace. Get some cultural insight at Centro Storico Associazione Centro Storico and Passeggiata di Gianicolo. Step out of Rome with an excursion to Villa d'Este in Tivoli--about 48 minutes away. See some other sides of Rome: contemplate in the serene atmosphere at Abbazia di San Paolo fuori le Mura, wander the streets of Citta del Vaticano, make a trip to Piazza Venezia, and admire the striking features of Villa Borghese.

To see maps and tourist information, go to the Rome itinerary planner.

Traveling by train from Milan to Rome takes 3 hours. Alternatively, you can fly; or drive. When traveling from Milan in October, plan for somewhat warmer days and about the same nights in Rome: temperatures range from 26°C by day to 15°C at night. On the 7th (Tue), you'll have the morning to explore before heading back home.

Things to do in Rome

Historic Sites Museums Parks

Side Trips

Vatican City, Villa d'Este
Find places to stay Oct 28 — Nov 7:
Highlights from your plan
Cupola di San Pietro ©
Cupola di San Pietro
Villa d'Este ©
Villa d'Este

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