19 days in Italy Itinerary

19 days in Italy Itinerary

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Route & dates

19 days in Italy Itinerary

Start: Munich
Fly:  4 h 45 min
1
Milan
— 1 day
Train:  1 h 15 min
2
Bologna
— 1 night
Train:  45 min
3
Florence
— 2 nights
Train:  1 h
4
Pisa
— 1 night
Drive:  1 h 30 min
5
San Gimignano
— 4 nights
Drive:  1 h 45 min
6
Lucca
— 2 nights
Drive:  3 h 30 min
7
Rome
— 3 nights
Train:  1 h
8
Orvieto
— 2 nights
Drive:  1 h 30 min
9
Assisi
— 3 nights
+2
Train + Tram + Fly:  7 h 15 min
End: Munich

1
day
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.
On the 24th (Tue), admire the striking features of Galleria Vittorio Emanuele II, then take in the architecture and atmosphere at Duomo di Milano, then make a trip to Piazza del Duomo, and finally explore the historical opulence of Castello Sforzesco.

For where to stay, more things to do, ratings, and tourist information, use the Milan trip planner .

Munich, Germany to Milan is an approximately 5-hour flight. You can also drive; or do a combination of flight and train. In December, daily temperatures in Milan can reach 9°C, while at night they dip to 1°C. Finish your sightseeing early on the 24th (Tue) to allow enough time to take a train to Bologna.

Things to do in Milan

Historic Sites Shopping
Find places to stay Dec 24 — 25:
Highlights from your plan
Duomo di Milano ©
Duomo di Milano
Galleria Vittorio Emanuele II ©
Galleria Vittorio Emanuele II
Castello Sforzesco ©
Castello Sforzesco

1
night
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 25th (Wed): contemplate the long history of Basilica di San Petronio, contemplate in the serene atmosphere at Basilica - Santuario di Santo Stefano, explore the world behind art at Pinacoteca Nazionale di Bologna, then contemplate the long history of Piazza Maggiore, and finally enjoy breathtaking views from Le Due Torri Torre degli Asinell.

To find traveler tips, where to stay, photos, and more tourist information, use the Bologna trip tool .

Traveling by train from Milan to Bologna takes 1.5 hours. Alternatively, you can drive; or take a bus. In December in Bologna, expect temperatures between 9°C during the day and 1°C at night. Finish your sightseeing early on the 25th (Wed) so you can take a train to Florence.

Things to do in Bologna

Historic Sites Museums
Find places to stay Dec 24 — 25:
Highlights from your plan
Piazza Maggiore ©
Piazza Maggiore
Le Due Torri Torre degli Asinell ©
Le Due Torri Torre degli Asinell
Basilica - Santuario di Santo Stefano ©

2
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Kick off your visit on the 26th (Thu): contemplate the long history of L’importuno di Michelangelo, examine the collection at Academy Of Florence Art Gallery, make a trip to Piazzale Michelangelo, then snap pictures at Ponte Vecchio, then appreciate the extensive heritage of Piazza del Duomo, and finally contemplate the long history of Cathedral of Santa Maria del Fiore. On your second day here, take an in-depth tour of Basilica di Santa Croce, explore the world behind art at Pitti Palace, steep yourself in history at Palazzo Vecchio, then get to know the fascinating history of Piazza della Signoria, and finally contemplate in the serene atmosphere at The Baptistery of St. John.

To see maps, ratings, other places to visit, and tourist information, read our Florence route planning site .

Traveling by train from Bologna to Florence takes an hour. Alternatively, you can take a bus; or drive. When traveling from Bologna in December, plan for a bit warmer days and about the same nights in Florence: temperatures range from 15°C by day to 4°C at night. Wrap up your sightseeing on the 27th (Fri) to allow time to take a train to Pisa.

Things to do in Florence

Historic Sites Museums
Find places to stay Dec 25 — 27:
Highlights from your plan
Cathedral of Santa Maria del Fiore ©
Cathedral of Santa Maria del Fiore
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

1
night
Pisa

Pisa ©
Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 28th (Sat), admire the striking features of Duomo di Pisa, then make a trip to Piazza dei Miracoli, and then enjoy breathtaking views from Leaning Tower of Pisa.

To see more things to do, other places to visit, maps, and more tourist information, go to the Pisa trip itinerary planning site .

Traveling by train from Florence to Pisa takes an hour. Alternatively, you can take a bus; or drive. In December, daytime highs in Pisa are 15°C, while nighttime lows are 4°C. Finish up your sightseeing early on the 28th (Sat) so you can go by car to San Gimignano.

Things to do in Pisa

Historic Sites
Find places to stay Dec 27 — 28:
Highlights from your plan
Duomo di Pisa ©
Duomo di Pisa
Leaning Tower of Pisa ©
Leaning Tower of Pisa
Piazza dei Miracoli ©
Piazza dei Miracoli

4
nights
San Gimignano

San Gimignano ©
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.
Venture out of the city with trips to Siena (Piazza del Campo, Torre del Mangia, & more). And it doesn't end there: learn about winemaking at Guardastelle Vineyard, enjoy breathtaking views from Torre Salvucci Maggiore, don't miss a visit to Piazza della Cisterna, and take an in-depth tour of Torre e Casa Campatelli.

For more things to do, photos, ratings, and other tourist information, refer to the San Gimignano holiday planner .

Getting from Pisa to San Gimignano by car takes about 1.5 hours. Other options: take a train; or take a bus. In December, daytime highs in San Gimignano are 15°C, while nighttime lows are 4°C. Wrap up your sightseeing by early afternoon on the 1st (Wed) to allow time for the car ride to Lucca.

Things to do in San Gimignano

Historic Sites Wineries Museums

Side Trips

Siena, Castello di Monteriggioni
Find places to stay Dec 28 — Jan 1:
Highlights from your plan
Guardastelle Vineyard ©
Guardastelle Vineyard
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

2
nights
Lucca

Lucca ©
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 1st (Wed): enjoy breathtaking views from Torre Guinigi, take in the architecture and atmosphere at Chiesa di Sant'Anastasio, and then admire the striking features of St Martin Cathedral. Get ready for a full day of sightseeing on the 2nd (Thu): contemplate in the serene atmosphere at San Michele in Foro, don't miss a visit to Piazza Anfiteatro, steep yourself in history at Le mura di Lucca, make a trip to Montecatini Alto, then contemplate in the serene atmosphere at Chiesa di San Leone, and finally ponder the design of Fontana Guidotti.

To find reviews and tourist information, refer to the Lucca journey maker tool .

You can drive from San Gimignano to Lucca in 2 hours. Other options are to take a train; or take a bus. Expect a daytime high around 13°C in January, and nighttime lows around 3°C. Wrap up your sightseeing on the 3rd (Fri) early enough to drive to Rome.

Things to do in Lucca

Historic Sites Childrens Museums Museums

Side Trips

Montecatini Terme, Parco di Pinocchio, Chiesa di San Leone
Find places to stay Jan 1 — 3:
Highlights from your plan
St Martin Cathedral ©
St Martin Cathedral
Le mura di Lucca ©
Le mura di Lucca
Torre Guinigi ©
Torre Guinigi

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.
Kick off your visit on the 4th (Sat): explore the world behind art at Galleria Borghese, appreciate the extensive heritage of Piazza Navona, steep yourself in history at St. Peter's Basilica, then explore the ancient world of Pantheon, and finally don't miss a visit to Trevi Fountain. Get ready for a full day of sightseeing on the next day: explore the ancient world of Colosseum, then delve into the distant past at Palatine Hill, then steep yourself in history at Roman Forum, and finally don't miss a visit to Spanish Steps.

To see photos, traveler tips, reviews, and more tourist information, go to the Rome online journey builder .

Getting from Lucca to Rome by car takes about 3.5 hours. Other options: fly; or take a train. In January in Rome, expect temperatures between 15°C during the day and 4°C at night. Finish your sightseeing early on the 6th (Mon) to allow enough time to take a train to Orvieto.

Things to do in Rome

Historic Sites Museums

Side Trip

St. Peter's Basilica
Find places to stay Jan 3 — 6:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

2
nights
Orvieto

Orvieto ©
The striking town of Orvieto, perched on a volcanic cliff overlooking the Umbrian countryside, is known as the Green Heart of Italy.
Get out of town with these interesting Orvieto side-trips: Cascata delle Marmore (in Marmore) and Cascate del Mulino (in Saturnia). There's lots more to do: learn about winemaking at Decugnano dei Barbi, look for gifts at Bottega Artigiana Polifemo Cuoio, explore the fascinating underground world of Orvieto Underground, and take in panoramic vistas at Torre del Moro.

To find where to stay, other places to visit, ratings, and more tourist information, use the Orvieto trip website .

You can take a train from Rome to Orvieto in an hour. Alternatively, you can take a bus; or drive. Expect a daytime high around 12°C in January, and nighttime lows around 3°C. Cap off your sightseeing on the 8th (Wed) early enough to go by car to Assisi.

Things to do in Orvieto

Nature Parks Wineries

Side Trips

Cascata delle Marmore, Cascate del Mulino
Find places to stay Jan 6 — 8:
Highlights from your plan
Decugnano dei Barbi ©
Decugnano dei Barbi
Duomo di Orvieto ©
Duomo di Orvieto
Cascate del Mulino ©
Cascate del Mulino

3
nights
Assisi

Assisi ©
Rich in culture and religious tradition, Assisi is known as the birthplace of St.
Step out of Assisi with an excursion to Piazza Grande in Gubbio--about 58 minutes away. There's lots more to do: take in the architecture and atmosphere at Basilica Papale e Sacro Convento di San Francesco d'Assisi, do a tasting at Azienda Agraria Saio, contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli - Porziuncola, and admire the striking features of Basilica di Santa Chiara.

To see reviews, maps, traveler tips, and tourist information, refer to the Assisi online trip itinerary builder .

Drive from Orvieto to Assisi in 1.5 hours. Alternatively, you can take a train; or take a bus. In January in Assisi, expect temperatures between 11°C during the day and 2°C at night. Wrap up your sightseeing by early afternoon on the 11th (Sat) to allow enough time to travel back home.

Things to do in Assisi

Historic Sites Wineries Shopping

Side Trip

Piazza Grande
Find places to stay Jan 8 — 11:
Highlights from your plan
Azienda Agraria Saio ©
Azienda Agraria Saio
Museo della Porziuncola ©
Museo della Porziuncola

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