21 days in Italy Itinerary

21 days in Italy Itinerary

Created using Inspirock Italy trip itinerary builder

This plan was created by another user. Make it your plan

Route & dates

Start: Sao Paulo
Fly:  14 h 15 min
1
Rome
— 3 nights
Drive:  2 h 30 min
2
Siena
— 2 nights
Drive:  1 h
3
Montepulciano
— 2 nights
Drive:  1 h 45 min
4
Florence
— 4 nights
Train:  45 min
5
Bologna
— 2 nights
Drive:  1 h 45 min
6
Venice
— 3 nights
Drive:  3 h 15 min
7
Funes
— 1 day
Drive:  4 h
8
Milan
— 3 nights
Fly:  16 h
End: Sao Paulo

3
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, and museums. Your plan includes some of its best attractions: steep yourself in history at Colosseum, admire the masterpieces at Galleria Borghese, appreciate the extensive heritage of Piazza Navona, and delve into the distant past at Palatine Hill.

To see ratings, more things to do, reviews, and tourist information, use the Rome travel route planner.

Sao Paulo, Brazil to Rome is an approximately 14.5- hour flight. You can also do a combination of flight and train; or do a combination of bus and flight. The time zone difference when traveling from Sao Paulo to Rome is 4 hours. In May, plan for daily highs up to 28°C, and evening lows to 17°C. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Siena.

Things to do in Rome

Historic Sites Museums Neighborhoods

Side Trip

Vatican City
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
Trevi Fountain ©
Trevi Fountain

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Start off your visit on the 5th (Tue): awaken your taste buds at some of the top wineries in the area and then make a trip to Piazza del Campo. Get ready for a full day of sightseeing on the next day: make a trip to Porta Tufi, pause for some serene contemplation at Duomo di Siena, then admire the masterpieces at Museo dell'Opera Metropolitana, then browse the collection at Biblioteca Piccolomini, and finally take in panoramic vistas at Torre del Mangia.

For traveler tips, other places to visit, where to stay, and other tourist information, read our Siena vacation planner.

Traveling by car from Rome to Siena takes 2.5 hours. Alternatively, you can take a bus; or take a train. Plan for slightly colder nights when traveling from Rome in May since evenings lows in Siena dip to 13°C. Finish your sightseeing early on the 6th (Wed) to allow enough time to drive to Montepulciano.

Things to do in Siena

Tours Historic Sites Museums
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

2
nights
Montepulciano

Montepulciano ©
Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Kick off your visit on the 7th (Thu): learn about winemaking at Winery Solaria Patrizia Cencioni, contemplate the long history of Abbazia di Sant'Antimo, then do a tasting at Ciacci Piccolomini d'Aragona, then learn about winemaking at Icario Winery, and finally take in the spiritual surroundings of Tempio di San Biagio. Get ready for a full day of sightseeing on the next day: learn about winemaking at Azienda Agricola Ercolani, don't miss a visit to Piazza Grande a Montepulciano, do a tasting at Cantina Fattoria della Talosa, learn about winemaking at Az. Agr. Poliziano, then learn about winemaking at Tenuta Valdipiatta, and finally learn about winemaking at Avignonesi.

For traveler tips, reviews, photos, and tourist information, refer to the Montepulciano road trip planning tool.

Getting from Siena to Montepulciano by car takes about an hour. Other options: do a combination of train and bus; or take a bus. May in Montepulciano sees daily highs of 27°C and lows of 13°C at night. Finish up your sightseeing early on the 8th (Fri) so you can go by car to Florence.

Things to do in Montepulciano

Wineries Historic Sites

Side Trip

Montalcino
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Winery Solaria Patrizia Cencioni ©
Winery Solaria Patrizia Cencioni
Tenuta Valdipiatta ©
Tenuta Valdipiatta

4
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Florence is known for museums, historic sites, and shopping. Your plan includes some of its best attractions: make a trip to Piazzale Michelangelo, explore the world behind art at Florence Academy of Fine Arts, see the interesting displays at Pitti Palace, and take in the views from Ponte Vecchio.

To see maps, reviews, ratings, and other tourist information, use the Florence trip planning website.

You can drive from Montepulciano to Florence in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May, daily temperatures in Florence can reach 25°C, while at night they dip to 13°C. Finish your sightseeing early on the 12th (Tue) to allow enough time to take a train to Bologna.

Things to do in Florence

Historic Sites Museums Shopping
Highlights from your plan
M.G. Design ©
M.G. Design
Piazzale Michelangelo ©
Piazzale Michelangelo
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

2
nights
Bologna

Bologna ©
A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Start off your visit on the 12th (Tue): take in the architecture and atmosphere at Santuario di Madonna di San Luca, learn something new at Academya Lingue, then take in the spiritual surroundings of Basilica di San Domenico, then make a trip to Piazza Maggiore, and finally enjoy breathtaking views from Le Due Torri Torre degli Asinell. Get ready for a full day of sightseeing on the next day: contemplate the long history of Basilica di San Petronio, pause for some serene contemplation at Basilica - Santuario di Santo Stefano, don't miss a visit to Compianto sul Cristo Morto, make a trip to Mausoleo di Galla Placidia, then contemplate in the serene atmosphere at Basilica San Vitale, and finally admire the landmark architecture of Loggetta Lombardesca.

To find reviews, traveler tips, ratings, and tourist information, refer to the Bologna attractions planning tool.

Take a train from Florence to Bologna in an hour. Alternatively, you can take a bus; or drive. In May, plan for daily highs up to 27°C, and evening lows to 14°C. Cap off your sightseeing on the 14th (Thu) early enough to go by car to Venice.

Things to do in Bologna

Historic Sites Classes

Side Trip

Ravenna
Highlights from your plan
Basilica San Vitale ©
Basilica San Vitale
Le Due Torri Torre degli Asinell ©
Le Due Torri Torre degli Asinell
Academya Lingue ©
Academya Lingue

3
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.
Change things up with these side-trips from Venice: Padua (Kenny Random & Scrovegni Chapel). There's much more to do: explore the activities along Canal Grande, admire the landmark architecture of Basilica di San Marco, admire the masterpieces at Gallerie dell'Accademia, and take in the views from Ponte dei Sospiri.

To find maps, ratings, and more tourist information, go to the Venice trip itinerary maker website.

You can drive from Bologna to Venice in 2 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 26°C in May, and nighttime lows around 15°C. Wrap up your sightseeing on the 17th (Sun) to allow time to travel to Funes.

Things to do in Venice

Historic Sites Museums Nature

Side Trip

Padua
Highlights from your plan
Canal Grande ©
Canal Grande
Piazza San Marco ©
Piazza San Marco
Basilica di San Marco
Basilica di San Marco

1
day
Funes

Funes ©
Your day-by-day itinerary now includes Lago di Braies. Start off your visit on the 17th (Sun): contemplate the waterfront views at Lago di Braies, make a trip to Chiesetta di San Giovanni, then admire the verdant scenery at Val di Funes, and finally hit the slopes at Plose.

To find photos, ratings, maps, and more tourist information, use the Funes tour itinerary builder site.

Traveling by car from Venice to Funes takes 3.5 hours. In May, daily temperatures in Funes can reach 28°C, while at night they dip to 13°C. Cap off your sightseeing on the 17th (Sun) early enough to travel to Milan.

Things to do in Funes

Parks Nature Winter Sports

Side Trips

Lago di Braies, Plose
Highlights from your plan
Plose ©
Plose
Lago di Braies ©
Lago di Braies

3
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.
Start off your visit on the 18th (Mon): don't miss a visit to Galleria Vittorio Emanuele II, then contemplate in the serene atmosphere at Duomo di Milano, then appreciate the extensive heritage of Piazza del Duomo, and finally step into the grandiose world of Castello Sforzesco. Here are some ideas for day two: admire the masterpieces at Pinacoteca Ambrosiana, admire the masterpieces at Pinacoteca di Brera, then explore the different monuments and memorials at Monumental Cemetery, and finally admire the striking features of Casa Barelli.

To see ratings, reviews, more things to do, and other tourist information, refer to the Milan trip itinerary planner.

Drive from Funes to Milan in 4 hours. In May, plan for daily highs up to 26°C, and evening lows to 15°C. On the 20th (Wed), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Milan

Historic Sites Museums Shopping
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana

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