37 days in Italy Itinerary

37 days in Italy Itinerary

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Route & dates

37 days in Italy Itinerary

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

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.
Do some cultural sightseeing at Colosseum and Piazza Navona. Get in touch with nature at Catacombe di San Callisto and Colle del Gianicolo. Go for a jaunt from Rome to Tivoli to see Villa Adriana about 36 minutes away. There's much more to do: steep yourself in history at St. Peter's Basilica, admire the masterpieces at Vatican Museums, make a trip to Roman Forum, and take in the architecture and atmosphere at Church of St. Louis of the French.

For traveler tips, photos, other places to visit, and other tourist information, read our Rome day trip planning site .

Sao Paulo, Brazil to Rome is an approximately 15-hour combination of bus and flight. You can also do a combination of bus, flight, and train. You'll lose 4 hours traveling from Sao Paulo to Rome due to the time zone difference. May in Rome sees daily highs of 28°C and lows of 17°C at night. Finish your sightseeing early on the 20th (Wed) so you can take a train to Naples.

Things to do in Rome

Historic Sites Museums Nature

Side Trips

Vatican City, Villa Adriana
Find places to stay May 16 — 20:
Highlights from your plan
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica
Vatican Museums
Vatican Museums

6
nights
Naples

Naples ©
Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. Pompeii Archaeological Park and Galleria Borbonica are good opportunities to explore the local culture. Your inner history buff will appreciate Museo Cappella Sansevero and Catacombe di San Gaudioso. Explore Naples' surroundings by going to Castello Aragonese d'Ischia (in Ischia) and Vesuvio National Park (in Ottaviano). There's lots more to do: see the interesting displays at Museo Archeologico Nazionale di Napoli, explore the ancient world of Parco Acheologico di Ercolano, explore the world behind art at Museo e Real Bosco di Capodimonte, and make a trip to Acquaquiglia del Pozzaro.

To see maps, reviews, where to stay, and other tourist information, read our Naples road trip app .

Traveling by train from Rome to Naples takes 1.5 hours. Alternatively, you can drive; or take a bus. Expect a daytime high around 27°C in May, and nighttime lows around 17°C. Wrap up your sightseeing on the 26th (Tue) early enough to drive to Siena.

Things to do in Naples

Historic Sites Museums Nature

Side Trips

Parco Acheologico di Ercolano, Vesuvio National Park, Pompeii Archaeological Park, Castello Aragonese d'Ischia
Find places to stay May 20 — 26:
Highlights from your plan
Pompeii Archaeological Park ©
Pompeii Archaeological Park
Museo Cappella Sansevero ©
Museo Cappella Sansevero
Galleria Borbonica ©
Galleria Borbonica

5
nights
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Museum-lovers will appreciate Palazzo Pubblico and Museo Civico and Museo dell'Opera Metropolitana. Get a sense of the local culture at Duomo di Siena and Castello di Monterinaldi. Get out of town with these interesting Siena side-trips: San Gimignano (Historic Centre of San Gimignano & Torre Grossa), Abbazia di San Galgano (in Chiusdino) and Cascate del Mulino (in Saturnia). There's much more to do: contemplate the long history of Centro Storico di Siena, make a trip to Piazza del Campo, step into the grandiose world of Castello delle Quattro Torri, and contemplate in the serene atmosphere at Chiesa di San Giorgio.

To find reviews, traveler tips, other places to visit, and other tourist information, you can read our Siena trip planner .

Traveling by car from Naples to Siena takes 4.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Naples in May, plan for little chillier nights in Siena, with lows around 13°C. Wrap up your sightseeing on the 31st (Sun) to allow time to drive to Venice.

Things to do in Siena

Historic Sites Outdoors Nature

Side Trips

San Gimignano, Val d'Orcia, Abbazia di San Galgano, Castello di Monterinaldi, Cascate del Mulino
Find places to stay May 26 — 31:
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Duomo di Siena ©
Duomo di Siena
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

6
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.
Piazza San Marco and Doge's Palace are good opportunities to explore the local culture. Museum-lovers will get to explore Peggy Guggenheim Collection and Ca' d'Oro. Explore Venice's surroundings by going to Padua (Basilica di Sant’Antonio, Chiesa degli Eremitani, & more). Next up on the itinerary: contemplate the waterfront views at Canal Grande, get to know the fascinating history of Centro Storico di Venezia, take in panoramic vistas at St Mark's Campanile, and pause for some serene contemplation at San Giorgio Maggiore.

To see ratings, other places to visit, traveler tips, and tourist information, read our Venice tour itinerary maker site .

Traveling by car from Siena to Venice takes 3.5 hours. Alternatively, you can take a train; or take a bus. In May, plan for daily highs up to 26°C, and evening lows to 15°C. Finish up your sightseeing early on the 6th (Sat) so you can catch the train to Florence.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Find places to stay May 31 — Jun 6:
Highlights from your plan
Piazza San Marco ©
Piazza San Marco
Doge's Palace ©
Doge's Palace
Basilica di San Marco
Basilica di San Marco

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Let the collections at Academy Of Florence Art Gallery and Church and Museum of Orsanmichele capture your imagination. Your inner history buff will appreciate Cathedral of Santa Maria del Fiore and Campanile di Giotto. Explore the numerous day-trip ideas around Florence: Canyon Park (in Bagni di Lucca), Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna (in Pratovecchio) and Leaning Tower of Pisa (in Pisa). There's much more to do: admire the masterpieces at Pitti Palace, steep yourself in history at Palazzo Vecchio, take in the views from Ponte Vecchio, and don't miss a visit to L’importuno di Michelangelo.

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

Take a train from Venice to Florence in 2.5 hours. Alternatively, you can drive; or take a bus. In June, daytime highs in Florence are 33°C, while nighttime lows are 21°C. Finish up your sightseeing early on the 12th (Fri) so you can catch the train to Verona.

Things to do in Florence

Parks Nature Outdoors

Side Trips

Canyon Park, Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna, Leaning Tower of Pisa, Botanical Garden Maria Ansaldi Pania di Corfino
Find places to stay Jun 6 — 12:
Highlights from your plan
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Cathedral of Santa Maria del Fiore ©
Pitti Palace ©
Pitti Palace

6
nights
Verona

Verona ©
The famous setting for Shakespeare's star-crossed lovers, Romeo and Juliet, Verona is one of northern Italy's main tourist destinations, largely owing to its incredibly rich artistic heritage.
Visit Arena di Verona and Basilica di San Zeno Maggiore for their historical value. Get outdoors at Scuola Italiana di Sci & Snowboard Kristal and Parco Naturalistico delle Cascate-Family. Explore the numerous day-trip ideas around Verona: Gruppo Dolomitico Sciliar-Catinaccio, Latemar - UNESCO (in Trento), Valsaviore (in Saviore dell'Adamello) and Lago di Garda (in Garda). There's still lots to do: explore the historical opulence of Museo di Castelvecchio, take in the architecture and atmosphere at Cappella dei Notai, get a new perspective on things with Boat Tours & Water Sports, and see the interesting displays at Casa di Giulietta.

For traveler tips, other places to visit, maps, and tourist information, refer to the Verona trip planner .

Getting from Florence to Verona by train takes about 2 hours. Other options: drive; or take a bus. Expect a daytime high around 34°C in June, and nighttime lows around 20°C. Finish up your sightseeing early on the 18th (Thu) so you can catch the train to Milan.

Things to do in Verona

Parks Nature Outdoors

Side Trips

Gruppo Dolomitico Sciliar-Catinaccio, Latemar - UNESCO, Scuola Italiana di Sci & Snowboard Kristal, Valsaviore, Lago di Garda
Find places to stay Jun 12 — 18:
Highlights from your plan
Basilica di San Zeno Maggiore ©
Basilica di San Zeno Maggiore
Museo di Castelvecchio ©
Museo di Castelvecchio

2
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.
Do some cultural sightseeing at Duomo di Milano and Castello Sforzesco. Visit Monumental Cemetery and Piazza del Duomo for their historical value. Change things up with a short trip to Museo Egizio in Turin (about 1h 30 min away). There's much more to do: get advice or help at Pinacoteca Ambrosiana, admire the landmark architecture of Galleria Vittorio Emanuele II, contemplate in the serene atmosphere at Chiesa di San Maurizio al Monastero Maggiore, and admire the masterpieces at Pinacoteca di Brera.

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

Traveling by train from Verona to Milan takes 1.5 hours. Alternatively, you can drive. In June, daily temperatures in Milan can reach 33°C, while at night they dip to 20°C. Finish up your sightseeing early on the 20th (Sat) so you can travel back home.

Things to do in Milan

Historic Sites Museums Shopping

Side Trip

Museo Egizio
Find places to stay Jun 18 — 20:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Museo Egizio ©
Museo Egizio
Castello Sforzesco ©
Castello Sforzesco

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