28 days in Italy Itinerary

28 days in Italy Itinerary

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Route & dates

28 days in Italy Itinerary

Start: Sao Paulo
Fly:  16​h
1
Milan
— 2 nights
Drive:  3​h
2
Florence
— 3 nights
bus:  45​min
3
Greve in Chianti
— 1 night
Drive:  1​h
4
Siena
— 3 nights
Drive:  1​h
5
Montalcino
— 1 day
Drive:  2​h 30​min
6
Rome
— 3 nights
Fly + Drive:  5​h
7
Ferrandina
— 3 nights
+2
Drive + Fly + Drive:  8​h 30​min
8
Capri, Island of Capri
— 3 nights
+2
ferry + shuttle + Fly:  5​h 15​min
9
Palermo
— 2 nights
Drive:  3​h
10
Syracuse
— 1 night
+2
Drive + Fly + Drive:  5​h
11
Ferrandina
— 1 night
Drive + Fly:  5​h 30​min
12
Milan
— 2 nights
Fly:  16​h
End: Sao Paulo


Learn more about your trip

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.
Kick off your visit on the 23rd (Sun): make a trip to Galleria Vittorio Emanuele II, then take in the spiritual surroundings of Duomo di Milano, then make a trip to Piazza del Duomo, and finally step into the grandiose world of Castello Sforzesco. Get ready for a full day of sightseeing on the 24th (Mon): take in the local highlights with Walking tours, then admire the striking features of Chiesa di San Maurizio al Monastero Maggiore, and then steep yourself in history at Il Cenacolo.

To see reviews, photos, where to stay, and more tourist information, read our Milan route planner .

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. Traveling from Sao Paulo to Milan, you'll lose 4 hours due to the time zone difference. Prepare for somewhat warmer weather when traveling from Sao Paulo in August: high temperatures in Milan hover around 34°C and lows are around 22°C. Finish your sightseeing early on the 25th (Tue) so you can take a train to Florence.

Things to do in Milan

Historic Sites Tours Shopping
Find places to stay Aug 23 — 25:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

3
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Step out of Florence with an excursion to Leaning Tower of Pisa in Pisa--about 1h 10 min away. There's lots more to do: admire the masterpieces at Gallerie Degli Uffizi, take in the spiritual surroundings of Cathedral of Santa Maria del Fiore, examine the collection at Pitti Palace, and make a trip to Piazzale Michelangelo.

To find reviews, maps, traveler tips, and other tourist information, you can read our Florence trip app .

Take a train from Milan to Florence in 2 hours. Alternatively, you can drive; or fly. In August, daytime highs in Florence are 35°C, while nighttime lows are 20°C. On the 28th (Fri), you'll have the morning to explore before heading off to Greve in Chianti.

Things to do in Florence

Historic Sites Museums Parks

Side Trip

Leaning Tower of Pisa
Find places to stay Aug 25 — 28:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

1
night
Greve in Chianti

Greve in Chianti ©
On the 28th (Fri), learn about winemaking at Castello di Verrazzano and then learn about winemaking at Enoteca Falorni.

Plan trip to Greve in Chianti with our itinerary maker to find out where to go and what to do.

Take a bus from Florence to Greve in Chianti in an hour. Alternatively, you can drive. In August, plan for daily highs up to 35°C, and evening lows to 20°C. Finish up your sightseeing early on the 29th (Sat) so you can go by car to Siena.

Things to do in Greve in Chianti

Wineries Historic Sites Shopping
Find places to stay Aug 28 — 29:
Highlights from your plan
Castello di Verrazzano ©
Castello di Verrazzano
Enoteca Falorni ©
Enoteca Falorni

3
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 29th (Sat): pause for some serene contemplation at Basilica Cateriniana Di S. Domenico. Get ready for a full day of sightseeing on the 30th (Sun): let your taste buds guide you at a local gastronomic tour, then pause for some serene contemplation at Duomo di Siena, and then don't miss a visit to Piazza del Campo.

For photos, maps, more things to do, and other tourist information, go to the Siena attractions planner .

Getting from Greve in Chianti to Siena by car takes about an hour. Other options: take a bus; or do a combination of bus and train. Expect a daytime high around 37°C in August, and nighttime lows around 22°C. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Montalcino.

Things to do in Siena

Historic Sites Tours
Find places to stay Aug 29 — Sep 1:
Highlights from your plan
Food Tours
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

1
day
Montalcino

Montalcino ©
In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
Kick off your visit on the 1st (Tue): learn about winemaking at Podere Il Cocco, learn about winemaking at Ciacci Piccolomini d'Aragona, and then steep yourself in history at Abbazia di Sant'Antimo.

To see other places to visit, reviews, traveler tips, and tourist information, read our Montalcino trip planner .

You can drive from Siena to Montalcino in an hour. Other options are to do a combination of train and bus; or take a bus. Expect a daytime high around 32°C in September, and nighttime lows around 19°C. Finish your sightseeing early on the 1st (Tue) so you can drive to Rome.

Things to do in Montalcino

Wineries Historic Sites
Find places to stay Sep 1 — 2:
Highlights from your plan
Ciacci Piccolomini d'Aragona ©
Ciacci Piccolomini d'Aragona
Podere Il Cocco ©
Podere Il Cocco
Abbazia di Sant'Antimo ©
Abbazia di Sant'Antimo

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.
On the 2nd (Wed), ponder the design of Trevi Fountain, delve into the distant past at Pantheon, get to know the fascinating history of Piazza Navona, then contemplate the long history of St. Peter's Basilica, and finally explore the ancient world of Colosseum. On the next day, steep yourself in history at Palatine Hill, explore the world behind art at Vatican Museums, and then don't miss a visit to Spanish Steps.

For reviews, other places to visit, ratings, and other tourist information, you can read our Rome trip itinerary maker app .

Traveling by car from Montalcino to Rome takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. September in Rome sees daily highs of 32°C and lows of 18°C at night. Finish your sightseeing early on the 4th (Fri) so you can travel to Ferrandina.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Sep 1 — 4:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

3
nights
Ferrandina

Ferrandina ©
Ferrandina is a town and comune in the province of Matera, in the Southern Italian region of Basilicata. You'll find plenty of places to visit near Ferrandina: Castelmezzano (Gradinata Normanna & Volo dell'Angelo), Centro Storico di Craco (in Craco) and Museo Archeologico Nazionale di Metaponto (in Metaponto). There's much more to do: enjoy the sand and surf at Spiagge Le Praie, take in the spiritual surroundings of Monastero di Santa Chiara, explore the wealth of natural beauty at Ente Parco Nazionale Del Pollino, and contemplate the long history of Convento di San Domenico.

To see where to stay, more things to do, and other tourist information, you can read our Ferrandina planner .

Use the Route module to find suitable travel options from Rome to Ferrandina. In September, daily temperatures in Ferrandina can reach 32°C, while at night they dip to 20°C. You will have some time to spend on the 7th (Mon) before leaving for Capri.

Things to do in Ferrandina

Parks Nature Historic Sites

Side Trips

Castelmezzano, Spiagge Le Praie, Museo Archeologico Nazionale di Metaponto, Centro Storico di Craco, Ente Parco Nazionale Del Pollino
Find places to stay Sep 4 — 7:
Highlights from your plan
Ente Parco Nazionale Del Pollino ©
Ente Parco Nazionale Del Pollino
Volo dell'Angelo ©
Volo dell'Angelo

3
nights
Capri, Island of Capri

Capri
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
Start off your visit on the 8th (Tue): explore the fascinating underground world of Blue Grotto, explore the activities along Marina Piccola, get great views at Belvedere Cannone, then take in nature's colorful creations at Giardini di Augusto, then explore the striking landscape at I Faraglioni, and finally take a memorable drive along Via Krupp. Get ready for a full day of sightseeing on the next day: get engrossed in the history at Villa San Michele, delve into the distant past at Villa Jovis, then explore the fascinating underground world of White Grotta, then pause for some photo ops at Natural Arch, and finally kick back and relax at Marina Grande Public Beach.

To find ratings, photos, more things to do, and more tourist information, read Capri trip itinerary builder app .

The Route module can help you plan travel from Ferrandina to Capri. Expect a daytime high around 31°C in September, and nighttime lows around 23°C. Wrap up your sightseeing by early afternoon on the 10th (Thu) to allow time for travel to Palermo.

Things to do in Capri

Parks Historic Sites Nature

Side Trip

Anacapri
Find places to stay Sep 7 — 10:
Highlights from your plan
I Faraglioni
I Faraglioni
Belvedere Cannone ©
Belvedere Cannone
White Grotta ©
White Grotta

2
nights
Palermo

The capital of Sicily, Palermo was founded by the Phoenicians under the name of Ziz.
On the 11th (Fri), take in the architecture and atmosphere at Duomo di Monreale, explore the different monuments and memorials at Catacombe dei Cappuccini, pause for some serene contemplation at Chiesa Inferiore della Cappella Palatina, then contemplate the long history of Norman Palace, and finally pause for some serene contemplation at Cattedrale di Palermo. On the 12th (Sat), you'll have a packed day of sightseeing: pause for some serene contemplation at Duomo di Cefalu, then contemplate the long history of Palazzo Conte Federico, then savor the flavors at Food & Drink, and finally don't miss a visit to Quattro Canti.

For maps, more things to do, ratings, and other tourist information, read our Palermo road trip site .

Traveling by combination of ferry and flight from Capri to Palermo takes 5.5 hours. Alternatively, you can do a combination of ferry, flight, and bus; or ride a ferry. Wrap up your sightseeing on the 12th (Sat) early enough to drive to Syracuse.

Things to do in Palermo

Historic Sites Tours

Side Trips

Duomo di Cefalu, Duomo di Monreale
Find places to stay Sep 10 — 12:
Highlights from your plan
Food Tours
Cattedrale di Palermo ©
Cattedrale di Palermo
Norman Palace ©
Norman Palace

1
night
Syracuse

Syracuse ©
Philosopher Cicero once described Syracuse as "the greatest Greek city and the most beautiful of them all." A powerful city-state of ancient Greece, Syracuse now is the capital of the eponymous Italian province on the eastern coast of Sicily.
Start off your visit on the 13th (Sun): contemplate the long history of Teatro Greco, then admire the striking features of Palazzo Benevantano del Bosco, then take in the architecture and atmosphere at Duomo di Siracusa, and finally step off the mainland to explore Ortigia. On the next day, take in the architecture and atmosphere at Chiesa Santa Chiara and then don't miss a visit to Centro Storico.

To see reviews, maps, where to stay, and more tourist information, refer to the Syracuse journey planner .

Traveling by car from Palermo to Syracuse takes 3 hours. Alternatively, you can take a bus; or take a train. On the 14th (Mon), wrap the sightseeing up by early afternoon so you can travel to Ferrandina.

Things to do in Syracuse

Historic Sites Nature Parks

Side Trip

Noto
Find places to stay Sep 12 — 14:
Highlights from your plan
Duomo di Siracusa ©
Duomo di Siracusa
Ortigia ©
Ortigia
Centro Storico ©
Centro Storico

1
night
Ferrandina

Ferrandina
To find maps, reviews, and other tourist information, read Ferrandina trip planner .

Explore your travel options from Syracuse to Ferrandina with the Route module. You will leave for Milan on the 15th (Tue).

Things to do in Ferrandina

Historic Sites Nightlife Wildlife
Find places to stay Sep 14 — 15:

2
nights
Milan

Milan ©
Step out of Milan with an excursion to Museo Egizio in Turin--about 1h 30 min away. Explore Milan further: admire the masterpieces at Pinacoteca Ambrosiana, explore the galleries of Basilica di Sant'Ambrogio, indulge your taste buds at Food & Drink, and catch a live performance at La Casa Maledetta.

To see traveler tips, other places to visit, ratings, and other tourist information, refer to the Milan road trip app .

Explore your travel options from Ferrandina to Milan with the Route module. Expect slightly colder temperatures when traveling from Ferrandina in September; daily highs in Milan reach 28°C and lows reach 16°C. Wrap up your sightseeing by early afternoon on the 17th (Thu) to allow enough time to travel back home.

Things to do in Milan

Museums Tours Nightlife

Side Trip

Museo Egizio
Find places to stay Sep 15 — 17:
Highlights from your plan
La Casa Maledetta ©
La Casa Maledetta
Pinacoteca Ambrosiana ©
Pinacoteca Ambrosiana
Museo Egizio ©
Museo Egizio

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