16 days in Italy Itinerary

Created using Inspirock Europe planner
Make it your trip
Fly
1
Rome
— 1 night
Drive
2
Assisi
— 1 night
Drive
3
Florence
— 2 nights
Drive
4
Montalcino
— 2 nights
Drive
5
San Gimignano
— 2 nights
Drive
6
Pisa
— 3 nights
Drive
7
Bologna
— 3 nights
Fly

S M T W T F S
11
12
13
14
15
16
17
18
19
20
21
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23
24
25
26
27
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29
30
1

Rome — 1 night

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 (Thu): get to know the fascinating history of Centro Storico Associazione Centro Storico, make a trip to Cupola di San Pietro, then steep yourself in history at St. Peter's Basilica, and finally delve into the distant past at Pantheon. Here are some ideas for day two: admire the landmark architecture of Villa Borghese, don't miss a visit to Piazza Navona, pause for some serene contemplation at Church of St. Louis of the French, then contemplate in the serene atmosphere at Chiesa di Sant'Ignazio di Loyola, then delve into the distant past at Colosseum, and finally steep yourself in history at Forum of Augustus.

For reviews, traveler tips, other places to visit, and more tourist information, you can read our Rome trip itinerary planner.

Lisbon, Portugal to Rome is an approximately 6.5-hour flight. You can also drive; or take a train. The time zone difference moving from Western European Standard Time (WET) to Central European Standard Time (CET) is 1 hour. In September in Rome, expect temperatures between 32°C during the day and 18°C at night. Wrap up your sightseeing on the 16th (Fri) to allow time to drive to Assisi.
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Side Trip
Find places to stay Sep 14 — 16:
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Assisi — 1 night

City of Peace

Rich in culture and religious tradition, Assisi is known as the birthplace of St.
On the 17th (Sat), pause for some serene contemplation at Chiesa Santo Stefano, then pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then take in the spiritual surroundings of Cripta di San Francesco, and finally take in the spiritual surroundings of Eremo delle Carceri.

To see reviews, maps, more things to do, and other tourist information, you can read our Assisi planning app.

You can drive from Rome to Assisi in 2.5 hours. Alternatively, you can take a train; or take a bus. In September, daytime highs in Assisi are 30°C, while nighttime lows are 16°C. Finish your sightseeing early on the 17th (Sat) to allow enough time to drive to Florence.
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Florence — 2 nights

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 18th (Sun): get to know the fascinating history of Centro Storico, admire the masterpieces at Florence Academy of Fine Arts, then pause for some serene contemplation at Basilica of Santa Croce, then take in the spiritual surroundings of The Baptistery of St. John, and finally appreciate the extensive heritage of Piazza della Signoria. Here are some ideas for day two: pause for some serene contemplation at Cathedral of Santa Maria del Fiore, appreciate the extensive heritage of Piazza del Duomo, then make a trip to Piazzale Michelangelo, and finally get great views at Basilica San Miniato al Monte.

To find other places to visit, ratings, and other tourist information, read Florence trip itinerary maker app.

Traveling by car from Assisi to Florence takes 2.5 hours. Alternatively, you can take a train. In September, daytime highs in Florence are 30°C, while nighttime lows are 17°C. Wrap up your sightseeing on the 19th (Mon) early enough to drive to Montalcino.
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Find places to stay Sep 17 — 19:
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Montalcino — 2 nights

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
On the 20th (Tue), learn about winemaking at Poggio Rubino, then do a tasting at il Cocco, and then learn about winemaking at NostraVita. On your second day here, awaken your taste buds at some of the top wineries in the area and then learn about winemaking at Winery Solaria Patrizia Cencioni.

To find photos, ratings, traveler tips, and more tourist information, read Montalcino trip planner.

Drive from Florence to Montalcino in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. In September in Montalcino, expect temperatures between 32°C during the day and 19°C at night. Wrap up your sightseeing on the 21st (Wed) to allow time to drive to San Gimignano.
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Wineries · Tours
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San Gimignano — 2 nights

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.
Kick off your visit on the 22nd (Thu): make a trip to Porta San Giovanni, then take in panoramic vistas at Rocca of Montestaffoli, then learn about winemaking at Podere La Marronaia- Le Colonne, and finally contemplate the long history of Torre Grossa. On the 23rd (Fri), you'll have a packed day of sightseeing: admire the landmark architecture of Mura di San Gimignano, then make a trip to Duomo di San Gimignano, then steep yourself in history at Historic Centre of San Gimignano, and finally get engrossed in the history at Torre e Casa Campatelli.

To find photos, more things to do, where to stay, and more tourist information, go to the San Gimignano day trip planner.

Traveling by car from Montalcino to San Gimignano takes 1.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. In September in San Gimignano, expect temperatures between 30°C during the day and 17°C at night. Finish your sightseeing early on the 23rd (Fri) so you can drive to Pisa.
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Historic Sites · Museums · Wineries
Find places to stay Sep 21 — 23:
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Pisa — 3 nights

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
Your cultural itinerary includes sights like Duomo di Pisa and Basilica of San Frediano. Popular historic sites such as Chiesa di Santa Maria della Spina and St Martin Cathedral are in your itinerary. Change things up with these side-trips from Pisa: Fortezza di Montecarlo (in Montecarlo) and Lucca (Chiesa e Battistero di San Giovanni e Santa Reparata & Le mura di Lucca). Next up on the itinerary: take in panoramic vistas at Leaning Tower of Pisa, make a trip to San Piero a Grado, and take in the architecture and atmosphere at Chiesa di Santa Caterina d'Alessandria.

To see photos, more things to do, where to stay, and tourist information, go to the Pisa driving holiday planning site.

Traveling by car from San Gimignano to Pisa takes 1.5 hours. Alternatively, you can take a train; or take a bus. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Bologna.
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Bologna — 3 nights

Heart of Italian Cuisine

A city famous for its cuisine, Bologna is the seat of the oldest university in the world, founded in 1088.
Visiting Torre Prendiparte and Associazione Vitruvio will get you outdoors. Do some cultural sightseeing at Basilica - Santuario di Santo Stefano and Basilica di San Domenico. There's lots more to do: contemplate in the serene atmosphere at Chiesa di Santa Maria della Vita, wander the streets of Quadrilatero, make a trip to Piazza Maggiore, and get to know the fascinating history of Portico di San Luca.

For more things to do, photos, traveler tips, and other tourist information, read Bologna trip itinerary maker site.

You can drive from Pisa to Bologna in 2 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Bologna can reach 30°C, while at night they dip to 17°C. Finish your sightseeing early on the 29th (Thu) so you can fly back home.
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Historic Sites · Outdoors · Neighborhoods · Wildlife
Find places to stay Sep 26 — 29:
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Italy travel guide

4.6
Landmarks · Ruins · Beaches
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.
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Province of Siena travel guide

4.3
Landmarks · Wineries & Vineyards · Churches
Siena is a city in Tuscany, Italy. It is the capital of the province of Siena.The historic centre of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation's most visited tourist attractions, with over 163,000 international arrivals in 2008. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year.HistorySiena, like other Tuscan hill towns, was first settled in the time of the Etruscans (c. 900–400 BC) when it was inhabited by a tribe called the Saina. The Etruscans were a tribe of advanced people who changed the face of central Italy through their use of irrigation to reclaim previously unfarmable land, and their custom of building their settlements in well-defended hill forts. A Roman town called Saena Julia was founded at the site in the time of the Emperor Augustus. Some archaeologists assert that Siena was controlled for a period by a Gaulish tribe called the Senones.According to local legend, Siena was founded by Senius and Aschius, two sons of Remus and thus nephews of Romulus, after whom Rome was named. Supposedly after their father's murder by Romulus, they fled Rome, taking with them the statue of the she-wolf suckling the infants (Capitoline Wolf), thus appropriating that symbol for the town. Additionally they rode white and black horses, giving rise to the Balzana, or coat of arms of Siena with a white band atop a dark band. Some claim the name Siena derives from Senius. Other etymologies derive the name from the Etruscan family name Saina, the Roman family name Saenii, or the Latin word senex "old" or its derived form seneo "to be old".

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