14 days in Italy Itinerary

14 days in Italy Itinerary

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Route & dates

14 days in Italy Itinerary

Start: Lisbon
+3
Fly + tram + train + bus:  7​h 30​min
1
Volterra
— 1 night
Drive:  2​h 45​min
2
Portoferraio
— 1 night
ferry + Drive:  3​h 15​min
3
Montepulciano
— 1 night
Drive:  1​h
4
Siena
— 2 nights
Drive:  1​h
5
Greve in Chianti
— 2 nights
bus:  45​min
6
Florence
— 3 nights
train:  1​h 45​min
7
Rome
— 3 nights
Fly:  5​h 45​min
End: Lisbon


Learn more about your trip

1
night
Volterra

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. On the 24th (Tue), make a trip to Piazza dei Priori, steep yourself in history at Roman Theatre, step into the grandiose world of Palazzo dei Priori, browse the exhibits of Palazzo Viti, then make a trip to Porta all'Arco, and finally examine the collection at Museo Etrusco Guarnacci.

Plan trip to Volterra with our itinerary maker to find out where to go and what to do.

Lisbon, Portugal to Volterra is an approximately 7.5-hour combination of flight and car. You can also drive. The time zone changes from Western European Time to Central European Time, which is usually a 1 hour difference. In September, daily temperatures in Volterra can reach 30°C, while at night they dip to 17°C. Finish your sightseeing early on the 24th (Tue) so you can drive to Portoferraio.

Things to do in Volterra

Historic Sites Museums
Find places to stay Sep 23 — 24:
Highlights from your plan
Palazzo dei Priori ©
Palazzo dei Priori
Porta all'Arco ©
Porta all'Arco
Palazzo Viti ©
Palazzo Viti

1
night
Portoferraio

Portoferraio
Portoferraio is a town and comune in the province of Livorno, on the edge of the eponymous harbour of the island of Elba. Kick off your visit on the 25th (Wed): kick back and relax at Spiaggia Canata, then enjoy the sand and surf at Spiaggia Stecchi, and then discover the deep blue sea with a scuba or snorkeling tour.

To find reviews, other places to visit, traveler tips, and tourist information, refer to the Portoferraio tour planner .

Getting from Volterra to Portoferraio by car takes about 3 hours. Expect a daytime high around 28°C in September, and nighttime lows around 19°C. Wrap up your sightseeing on the 25th (Wed) to allow time to travel to Montepulciano.

Things to do in Portoferraio

Parks Beaches Outdoors

Side Trip

Capoliveri
Find places to stay Sep 24 — 25:

1
night
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.
Start off your visit on the 26th (Thu): learn about winemaking at Avignonesi, learn about winemaking at Az. Agr. Poliziano, do a tasting at Tenuta Valdipiatta, then make a trip to Piazza Grande a Montepulciano, and finally learn about winemaking at Cantina Fattoria della Talosa.

To find other places to visit, more things to do, traveler tips, and other tourist information, go to the Montepulciano trip planner .

Traveling by combination of ferry and car from Portoferraio to Montepulciano takes 3.5 hours. Alternatively, you can do a combination of ferry, train, and bus. When traveling from Portoferraio in September, plan for a bit warmer days in Montepulciano, with highs around 32°C, while nights are about the same with lows around 19°C. Finish your sightseeing early on the 26th (Thu) to allow enough time to drive to Siena.

Things to do in Montepulciano

Wineries
Find places to stay Sep 25 — 26:
Highlights from your plan
Tenuta Valdipiatta ©
Tenuta Valdipiatta

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 27th (Fri): don't miss a visit to Piazza del Campo and then awaken your taste buds at some of the top wineries in the area. Here are some ideas for day two: steep yourself in history at Centro Storico di Siena, then pause for some serene contemplation at Duomo di Siena, then get lost in a book at Biblioteca Piccolomini, and finally enjoy breathtaking views from Torre del Mangia.

For more things to do, where to stay, traveler tips, and other tourist information, refer to the Siena online holiday planner .

Drive from Montepulciano to Siena in an hour. Alternatively, you can take a train; or take a bus. In September in Siena, expect temperatures between 32°C during the day and 19°C at night. Finish your sightseeing early on the 28th (Sat) so you can drive to Greve in Chianti.

Things to do in Siena

Historic Sites Tours
Find places to stay Sep 26 — 28:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

2
nights
Greve in Chianti

Greve in Chianti ©
On the 29th (Sun), look for gifts at Piccole Armonie Country, then do a tasting at Poggio al Bosco, then learn about winemaking at Castello di Verrazzano, and finally do a tasting at Enoteca Falorni. On your second day here, do a tasting at Fattoria di Montemaggio, do a tasting at Castello di Monterinaldi, then learn about winemaking at Accademia del Buon Gusto, and finally learn about winemaking at Montefioralle Winery.

To find maps, photos, more things to do, and other tourist information, go to the Greve in Chianti trip planner .

Getting from Siena to Greve in Chianti by car takes about an hour. Other options: take a bus; or do a combination of train and 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 30th (Mon) early enough to take a bus to Florence.

Things to do in Greve in Chianti

Wineries Historic Sites Shopping

Side Trips

Radda in Chianti, Poggio al Bosco
Find places to stay Sep 28 — 30:
Highlights from your plan
Fattoria di Montemaggio ©
Fattoria di Montemaggio
Castello di Verrazzano ©
Castello di Verrazzano
Enoteca Falorni ©
Enoteca Falorni

3
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, shopping, nightlife, and classes. Your plan includes some of its best attractions: admire the masterpieces at Gallerie Degli Uffizi, enjoy breathtaking views from Campanile di Giotto, get great views at Piazzale Michelangelo, and take an in-depth tour of Basilica di Santa Croce.

To find maps, traveler tips, where to stay, and other tourist information, read Florence holiday planner .

Traveling by bus from Greve in Chianti to Florence takes an hour. Alternatively, you can drive. In September in Florence, expect temperatures between 30°C during the day and 17°C at night. Wrap up your sightseeing on the 3rd (Thu) to allow time to take a train to Rome.

Things to do in Florence

Museums Historic Sites Tours
Find places to stay Sep 30 — Oct 3:
Highlights from your plan
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery
Piazzale Michelangelo ©
Piazzale Michelangelo

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.
Start off your visit on the 4th (Fri): steep yourself in history at Colosseum, contemplate the long history of Roman Forum, get to know the fascinating history of Piazza Navona, then delve into the distant past at Pantheon, and finally admire the local landmark of Trevi Fountain. Get ready for a full day of sightseeing on the next day: contemplate in the serene atmosphere at Vatican Museums, then don't miss a visit to St. Peter's Basilica, and then explore the ancient world of Palatine Hill.

Plan a Rome trip in moments using our itinerary builder.

Take a train from Florence to Rome in 2 hours. Alternatively, you can drive; or fly. October in Rome sees daily highs of 26°C and lows of 15°C at night. On the 6th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

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

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