29 days in Italy Itinerary

29 days in Italy Itinerary

Created using Inspirock Italy trip itinerary planner

Make it your trip
1
Milan
— 2 nights
Train
2
Venice
— 3 nights
Train
3
Rome
— 3 nights
Drive
4
Montepulciano
— 1 night
Drive
5
Volterra
Drive
6
San Gimignano
— 1 night
Drive
7
Greve in Chianti
— 1 day
Drive
8
Siena
— 1 night
Drive
9
Lucca
— 1 night
Drive
10
Florence
— 3 nights
Train
11
Naples
Ferry
12
Capri
— 3 nights
Ferry
13
Naples
Drive
14
Positano
— 1 night
Drive
15
Matera
— 1 night
Drive
16
Gallipoli
— 1 night
Drive
17
Sant'Andrea
Drive
18
Lecce
— 1 night
Drive
19
Cisternino
— 1 night
Drive
20
Locorotondo
Drive
21
Polignano a Mare
Drive
22
Ostuni
— 2 nights
Drive
23
Pompeii
— 1 night
Drive
24
Arezzo
— 1 night
Drive
25
Milan
— 1 night

S M T W T F S
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9

Milan

— 2 nights

Fashion Capital of World

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.
On the 10th (Fri), examine the collection at Museo del Novecento, admire the masterpieces at Museum of Decorative Arts, and then explore the world behind art at Museo Pieta Rondanini. Get ready for a full day of sightseeing on the next day: take in the architecture and atmosphere at Certosa di Milano, then see La Casa Maledetta, and then tee off at Revival Minigolf.

Inspirock's itinerary builder makes planning a Milan trip simple and quick.

If you are flying in from Mexico, the closest major aiports are Malpensa International Airport, Milano Linate Airport and Milan Bergamo Airport. In September, plan for daily highs up to 28°C, and evening lows to 16°C. On the 12th (Sun), you'll travel to Venice.

Things to do in Milan

Museums · Nightlife · Fun & Games · Historic Sites

Side Trip

Venice

— 3 nights

City of Romance

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.
Your cultural itinerary includes sights like Basilica dei Santi Giovanni e Paolo (San Zanipolo) and Church of San Pantalon. Discover out-of-the-way places like Santa Maria dei Miracoli and Santa Croce. And it doesn't end there: pause for some serene contemplation at Chiesa di San Giorgio dei Greci, wander the streets of Campo Santa Margherita, explore the world behind art at Palazzo Fortuny (Pesaro degli Orfei), and get a new perspective on things with Like a Venetian.

To see traveler tips, ratings, more things to do, and other tourist information, go to the Venice sightseeing site.

You can drive from Milan to Venice in 3 hours. Other options are to take a train; or take a bus. September in Venice sees daily highs of 29°C and lows of 17°C at night. On the 15th (Wed), you'll have the morning to explore before heading off to Rome.

Things to do in Venice

Historic Sites · Neighborhoods · Tours · Outdoors

Rome

— 3 nights

Eternal City

Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
Kick off your visit on the 15th (Wed): head outdoors with Nuoto Aurelia. On your second day here, take in the spiritual surroundings of Basilica of the Holy Cross in Jerusalem, take in the awesome beauty at Colle Aventino, visit Ghetto Ebraico, then pause for some photo ops at Trajan's Column, and finally take in nature's colorful creations at Monte Pincio.

To see traveler tips, reviews, photos, and other tourist information, read Rome road trip site.

You can fly from Venice to Rome in 3 hours. Other options are to take a train; or drive. In September in Rome, expect temperatures between 32°C during the day and 18°C at night. You will leave for Montepulciano on the 18th (Sat).

Things to do in Rome

Outdoors · Parks · Historic Sites · Beaches

Side Trip

Montepulciano

— 1 night

Pearl of the 16th Century

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
On the 18th (Sat), learn about winemaking at Enoteca Croce Di Febo Biologica and then get to know the fascinating history of Via di Gracciano nel Corso.

To see maps, other places to visit, reviews, and other tourist information, use the Montepulciano visit planner.

Drive from Rome to Montepulciano in 2 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 32°C in September, and nighttime lows around 19°C. Wrap up your sightseeing on the 19th (Sun) early enough to drive to Volterra.

Things to do in Montepulciano

Wineries · Historic Sites

Volterra

Volterra is a walled mountaintop town in the Tuscany region of Italy of which its history dates to before the 7th century BC and has substantial structures from the Etruscan, Roman, and Medieval periods.HistoryVolterra, known to the ancient Etruscans as Velathri or Vlathri and to the Romans as Volaterrae, is a town and comune in the Tuscany region of Italy. To see other places to visit, traveler tips, reviews, and more tourist information, read Volterra visit website.

Getting from Montepulciano to Volterra by car takes about 2 hours. Other options: do a combination of train and taxi; or take a bus. In September in Volterra, expect temperatures between 30°C during the day and 17°C at night. You will leave for San Gimignano on the 19th (Sun).

Things to do in Volterra

Historic Sites · Outdoors · Parks · Nightlife

San Gimignano

— 1 night

Town of Fine Towers

A historical gem in the heart of Tuscany, San Gimignano is known as the Town of Fine Towers for its jutting skyline of high city walls.
Start off your visit on the 19th (Sun): take in the exciting artwork at Oibo Re-Design, then take in the exciting artwork at Vitalita Cultural Association, and then see the interesting displays at Galerie Peugeot.

To see traveler tips, more things to do, other places to visit, and more tourist information, go to the San Gimignano trip builder website.

Traveling by car from Volterra to San Gimignano takes an hour. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Finish your sightseeing early on the 20th (Mon) to allow enough time to drive to Greve in Chianti.

Things to do in San Gimignano

Museums · Shopping

Greve in Chianti

— 1 day
Kick off your visit on the 20th (Mon): learn about winemaking at Azienda Agricola Altiero (Winery), awaken your taste buds at Azienda Agricola Brogioni Maurizio, then do a tasting at Poggio al Sole Winery, then learn about winemaking at Monte Bernardi, and finally learn about winemaking at Fattoria Le Fonti.

To find ratings, maps, traveler tips, and more tourist information, go to the Greve in Chianti road trip planning tool.

Drive from San Gimignano to Greve in Chianti in an hour. Alternatively, you can do a combination of train and bus; or take a bus. In September, daily temperatures in Greve in Chianti can reach 30°C, while at night they dip to 17°C. Wrap up your sightseeing on the 20th (Mon) early enough to drive to Siena.

Things to do in Greve in Chianti

Wineries · Tours

Side Trip

Siena

— 1 night

Cultural Heart of Tuscany

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 21st (Tue), look for gifts at Antica Siena.

To see maps, photos, where to stay, and other tourist information, refer to the Siena online journey planner.

You can drive from Greve in Chianti to Siena in an hour. Alternatively, you can take a bus; or do a combination of bus and train. September in Siena sees daily highs of 32°C and lows of 19°C at night. Wrap up your sightseeing by early afternoon on the 21st (Tue) to allow enough time to drive to Lucca.

Things to do in Siena

Shopping
Highlights from your trip

Lucca

— 1 night

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
Kick off your visit on the 21st (Tue): examine the collection at Antica Tipografia Biagini.

Plan my trip to Lucca with suggested itineraries provided by Inspirock.

Drive from Siena to Lucca in 2 hours. Alternatively, you can take a train; or do a combination of bus and train. In September, daytime highs in Lucca are 30°C, while nighttime lows are 17°C. Wrap up your sightseeing by early afternoon on the 22nd (Wed) to allow time for the car ride to Florence.

Things to do in Lucca

Museums · Tours · Parks

Side Trip

Florence

— 3 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Get a sense of the local culture at Palazzo Strozzi and Corridoio Vasariano. You'll discover tucked-away gems like Mus.e Firenze Palazzo Vecchio and Convento di San Francesco. There's still lots to do: wander the streets of Oltrarno, stroll through Lido Di Camaiore, enjoy breathtaking views from Torre di Arnolfo, and take an in-depth tour of Museo dell'Opera di Santa Croce.

To find where to stay, reviews, and other tourist information, you can read our Florence tour planning site.

Getting from Lucca to Florence by car takes about 1.5 hours. Other options: take a bus; or take a train. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Finish up your sightseeing early on the 25th (Sat) so you can catch the train to Naples.

Things to do in Florence

Museums · Historic Sites · Beaches · Neighborhoods

Side Trip

Naples

Naples is the capital of the Italian region Campania and the third-largest municipality in Italy after Rome and Milan. To see ratings, reviews, maps, and more tourist information, go to the Naples trip tool.

Take a train from Florence to Naples in 3 hours. Alternatively, you can do a combination of flight and train; or drive. In September, daily temperatures in Naples can reach 31°C, while at night they dip to 20°C. On the 25th (Sat), you'll travel to Capri.

Things to do in Naples

Historic Sites · Tours · Nightlife · Outdoors

Capri

— 3 nights
The island of Capri encompasses all the magical allure of the Mediterranean--dramatic blue waters, lush mountainous landscape, and picturesque island villages.
On the 26th (Sun), take some stellar pictures from Belvedere Cannone, enjoy breathtaking views from Belvedere di Tragara, and then make a trip to Via Camerelle. Keep things going the next day: explore the fascinating underground world of Grotta di Matromania, explore the fascinating underground world of White Grotta, and then get a dose of the wild on Nesea Capri.

To find maps, traveler tips, reviews, and other tourist information, you can read our Capri trip itinerary builder site.

Traveling by ferry from Naples to Capri takes 1.5 hours. In September, daily temperatures in Capri can reach 31°C, while at night they dip to 23°C. On the 28th (Tue), you'll travel to Naples.

Things to do in Capri

Parks · Nature · Tours · Outdoors

Naples

Kick off your visit on the 28th (Tue): explore the galleries of Complesso Museale Santa Maria delle Anime del Purgatorio ad Arco, then take a stroll through Chiaia, and then steep yourself in history at Basilica Santuario del Carmine Maggiore.

For photos, more things to do, traveler tips, and more tourist information, you can read our Naples sightseeing planner.

Traveling by ferry from Capri to Naples takes 1.5 hours. Wrap up your sightseeing on the 28th (Tue) to allow time to drive to Positano.

Things to do in Naples

Historic Sites · Neighborhoods · Shopping · Museums

Positano

— 1 night
Often referred to as the gem of the Amalfi Coast, Positano remains one of southern Italy's most sought-after vacation locales, thanks to its hillside location and picturesque, pastel buildings.
To find traveler tips, other places to visit, photos, and more tourist information, refer to the Positano road trip planner.

You can drive from Naples to Positano in 1.5 hours. Alternatively, you can take a bus. September in Positano sees daily highs of 31°C and lows of 23°C at night. You'll set off for Matera on the 29th (Wed).

Things to do in Positano

Tours · Outdoors · Transportation · Shopping

Matera

— 1 night

Subterranean City

Famous for its resemblance to the ancient settlements of Jerusalem and Cappadocia, Matera remains one of the oldest inhabited cities in the world.
On the 29th (Wed), contemplate the long history of Santuario Santa Maria di Picciano, pause for some serene contemplation at Chiesa dei Quattro Evangelisti, then steep yourself in history at Casa grotta del Casalnuovo, and finally admire the landmark architecture of Palazzo del Sedile.

To see ratings, photos, maps, and more tourist information, you can read our Matera sightseeing planning website.

You can drive from Positano to Matera in 3.5 hours. Other options are to do a combination of taxi, train, and bus; or take a bus. Traveling from Positano in September, plan for a bit cooler nights in Matera, with lows around 17°C. Cap off your sightseeing on the 30th (Thu) early enough to go by car to Gallipoli.

Things to do in Matera

Historic Sites

Gallipoli

— 1 night

Ionian Pearl

Deriving its name from the Greek for "beautiful city," Gallipoli retains the charm of an old fishing port.
Start off your visit on the 30th (Thu): get a new perspective on nature at Marea - Centro di Cultura del Mare, take in the architecture and atmosphere at Chiesa di San Domenico al Rosario, and then kick back and relax at Helios beach.

To see photos, ratings, where to stay, and tourist information, read Gallipoli trip planner.

Drive from Matera to Gallipoli in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. In September, daily temperatures in Gallipoli can reach 32°C, while at night they dip to 19°C. Wrap up your sightseeing on the 1st (Fri) early enough to drive to Sant'Andrea.

Things to do in Gallipoli

Childrens Museums · Beaches · Outdoors · Parks

Sant'Andrea

To see more things to do, ratings, reviews, and more tourist information, read our Sant'Andrea itinerary builder site.

Traveling by car from Gallipoli to Sant'Andrea takes an hour. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. You will leave for Lecce on the 1st (Fri).

Things to do in Sant'Andrea

Outdoors · Historic Sites

Lecce

— 1 night

Florence of the South

Known as the Florence of the South, Lecce is distinguished for its elaborate Baroque monuments.
Kick off your visit on the 1st (Fri): step into the grandiose world of Castello di Acaya, contemplate in the serene atmosphere at Saint Nicolo and Cataldo Church, and then take in the architecture and atmosphere at Gesuiti Chiesa del Gesu'.

Use Inspirock's suggestions to plan your Lecce trip and find the best activities and attractions for your vacation.

Drive from Sant'Andrea to Lecce in an hour. Expect a daytime high around 26°C in October, and nighttime lows around 15°C. Finish your sightseeing early on the 2nd (Sat) so you can drive to Cisternino.

Things to do in Lecce

Historic Sites

Side Trip

Cisternino

— 1 night
Cisternino is a comune in the province of Brindisi in Apulia, on the coast of south-eastern Italy, approximately 50km north-west of the city of Brindisi. On the 2nd (Sat), take in the architecture and atmosphere at Santuario della Madonna d'Ibernia, pause for some serene contemplation at Chiesa Matrice di San Nicola Patara, and then take in panoramic vistas at Torre Civica Normanno Sveva.

To find more things to do, other places to visit, where to stay, and more tourist information, read our Cisternino online journey planner.

Traveling by car from Lecce to Cisternino takes 1.5 hours. October in Cisternino sees daily highs of 26°C and lows of 17°C at night. Finish your sightseeing early on the 3rd (Sun) to allow enough time to travel to Locorotondo.

Things to do in Cisternino

Historic Sites

Locorotondo

Locorotondo is a town and comune of the Metropolitan City of Bari, Apulia, southern Italy, with a population of about 14,000. To see traveler tips, where to stay, other places to visit, and other tourist information, refer to the Locorotondo itinerary planning website.

Locorotondo is just a short distance from Cisternino. In October, daytime highs in Locorotondo are 26°C, while nighttime lows are 17°C. On the 3rd (Sun), you'll travel to Polignano a Mare.

Things to do in Locorotondo

Historic Sites · Outdoors · Nightlife · Parks

Polignano a Mare

Polignano a Mare is a town and comune in the Metropolitan City of Bari, Apulia, southern Italy, located on the Adriatic Sea. To find where to stay, maps, reviews, and other tourist information, you can read our Polignano a Mare tour itinerary builder website.

Traveling by car from Locorotondo to Polignano a Mare takes an hour. Expect a bit cooler evenings in Polignano a Mare when traveling from Locorotondo in October, with lows around 13°C. You'll set off for Ostuni on the 3rd (Sun).

Things to do in Polignano a Mare

Historic Sites · Outdoors · Nightlife · Parks

Ostuni

— 2 nights
Ostuni is a city and comune, located about 8 km from the coast, in the province of Brindisi, region of Apulia, Italy). On the 3rd (Sun), make a trip to Infopoint - Association Il Borgo Ostuni and then take in the architecture and atmosphere at Chiesa di San Francesco. On your second day here, take in the local highlights with Azienda Agricola Pietrasanta, then contemplate the long history of Arco Scoppa, and then enjoy the sand and surf at Spiaggia di Cala di Rosamarina.

To find maps, reviews, more things to do, and other tourist information, read our Ostuni vacation tool.

Drive from Polignano a Mare to Ostuni in an hour. Alternatively, you can take a train; or take a bus. Plan for somewhat warmer nights when traveling from Polignano a Mare in October since evenings lows in Ostuni dip to 17°C. Wrap up your sightseeing on the 5th (Tue) early enough to drive to Pompeii.

Things to do in Ostuni

Historic Sites · Outdoors · Beaches · Parks

Side Trip

Pompeii

— 1 night

Underground City

Pompeii has been a tourist destination for more than 250 years.
Kick off your visit on the 5th (Tue): delve into the distant past at House of Menander (Casa del Menandro), delve into the distant past at Casa della Fontana Grande, then delve into the distant past at Casa di Ottavio Quartione, then delve into the distant past at Termopolio di Vetuzio Placido, and finally delve into the distant past at Fullonica di Stephanus.

To see more things to do, reviews, and tourist information, go to the Pompeii day trip planner.

Traveling by car from Ostuni to Pompeii takes 4 hours. Alternatively, you can fly; or take a train. In October in Pompeii, expect temperatures between 27°C during the day and 17°C at night. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Arezzo.

Things to do in Pompeii

Historic Sites

Arezzo

— 1 night

Ancient City

Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
Kick off your visit on the 6th (Wed): learn about winemaking at Podere di Pomaio Green Winery, head outdoors with Azienda Agricola Villa Magna Tartufi, and then contemplate the long history of Borgo Medievale di Poppi. Keep things going the next day: see the interesting displays at Museo della Fauna Selvatica and then savor the flavors at Food & Drink.

For maps, ratings, reviews, and tourist information, go to the Arezzo trip website.

Traveling by car from Pompeii to Arezzo takes 4 hours. Alternatively, you can take a train; or do a combination of flight and train. Finish your sightseeing early on the 7th (Thu) so you can drive to Milan.

Things to do in Arezzo

Wineries · Tours · Historic Sites · Museums

Side Trips

Milan

— 1 night

Fashion Capital of World

On the 8th (Fri), get curious at Museo Della Scienza E Della Tecnologia Leonardo da Vinci.

To find traveler tips, where to stay, more things to do, and more tourist information, go to the Milan travel tool.

Getting from Arezzo to Milan by car takes about 4 hours. Other options: take a train; or fly.

Things to do in Milan

Childrens Museums · Museums

Italy travel guide

4.6
Landmarks · Ruins · Sacred & Religious Sites
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.

Puglia travel guide

4.1
Beaches · Landmarks · Churches
Situated at the southeastern tip of the country, Puglia forms the heel on the "boot" of Italy. First colonized by Mycenaean Greeks, the region flourished during Roman times as a major producer of grain and oil. Today, Puglia remains a predominantly agricultural part of the country, though its warm and sunny coastal weather makes it a favorite holiday destination with an ever-increasing number of tourists. The long coastline features attractions like sun-kissed beaches and lively resorts, many of which are overlooked by limestone cliffs. Deeper inland, Puglia is largely flat, a land of charming villages and world-class cuisine. Here, you'll find olive oil, grapes, tomatoes, peppers, mushrooms, and fresh seafood to give you sustenance as you continue sightseeing. Despite its reputation as a producer of some Italy's best food and wines, Puglia still has numerous rural corners that most tourists have yet to explore.