14 days in Italy Itinerary

14 days in Italy Itinerary

Created using Inspirock Italy visit planner

Plan created by another user.Make it yours

Route & dates

Start: Jacksonville
Fly:  16 h
1
Rome
— Few hours
Drive:  2 h
2
Perugia
— 1 night
Drive:  1 h 15 min
3
Arezzo
— Few hours
Drive:  1 h
4
Greve in Chianti
— Few hours
Drive:  45 min
5
Florence
— 6 nights
Drive:  1 h 15 min
6
Firenzuola
— 1 night
Drive:  1 h 45 min
7
Lucca
— Few hours
Drive:  30 min
8
Pisa
— Few hours
Drive:  30 min
9
Livorno
— Few hours
Drive:  2 h
10
Siena
— 1 night
Drive:  1 h 15 min
11
Seggiano
— Few hours
Drive:  2 h 45 min
12
Rome
— 3 nights
Fly:  16 h
End: Jacksonville

few
hours
Rome

Rome
Aptly nicknamed the Eternal City, Rome is the birthplace of the Roman Empire, one of the world's greatest civilizations ever.
To see more things to do, where to stay, photos, and other tourist information, you can read our Rome day trip app.

Jacksonville, USA to Rome is an approximately 16.5-hour flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Prepare for a bit cooler weather when traveling from Jacksonville in October: high temperatures in Rome hover around 73°F and lows are around 55°F. On the 27th (Sat), you'll travel to Perugia.

Things to do in Rome

Tours Historic Sites Nightlife

1
night
Perugia

Perugia ©
Though it features Etruscan defensive walls and a medieval town center, Perugia is perhaps best known for its fine chocolate and annual chocolate festival.
Start off your visit on the 27th (Sat): admire the striking features of San Pietro and then pause for some serene contemplation at Basilica di Santa Maria degli Angeli - Porziuncola.

For more things to do, photos, reviews, and more tourist information, you can read our Perugia trip planner.

Traveling by car from Rome to Perugia takes 2 hours. Alternatively, you can take a bus; or take a train. In October, plan for daily highs up to 70°F, and evening lows to 51°F. Finish your sightseeing early on the 28th (Sun) to allow enough time to drive to Arezzo.

Things to do in Perugia

Historic Sites

Side Trip

Basilica di Santa Maria degli Angeli - Porziuncola
Highlights from your plan
San Pietro ©
San Pietro

few
hours
Arezzo

Arezzo
Arezzo is a city of art with colorful frescoes and abundance of goldsmiths and antique jewelers.
To find ratings, traveler tips, more things to do, and tourist information, refer to the Arezzo trip itinerary planning app.

Drive from Perugia to Arezzo in 1.5 hours. Alternatively, you can take a train. You will leave for Greve in Chianti on the 28th (Sun).

Things to do in Arezzo

Historic Sites Wineries Tours

few
hours
Greve in Chianti

Greve in Chianti ©
On the 28th (Sun), learn about winemaking at Castello di Monterinaldi and then do a tasting at Accademia del Buon Gusto.

To find photos, other places to visit, maps, and other tourist information, read our Greve in Chianti holiday tool.

You can drive from Arezzo to Greve in Chianti in 1.5 hours. Other options are to take a train; or take a bus. October in Greve in Chianti sees daily highs of 71°F and lows of 54°F at night. Wrap up your sightseeing on the 28th (Sun) early enough to drive to Florence.

Things to do in Greve in Chianti

Wineries Historic Sites

Side Trip

Castello di Monterinaldi
Highlights from your plan
Accademia del Buon Gusto ©
Accademia del Buon Gusto
Castello di Monterinaldi ©
Castello di Monterinaldi

6
nights
Florence

Florence ©
Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
Your day-by-day itinerary now includes Tuscany Vespa Tours. Shop till you drop at San Quirico d'Orcia and Campolmi Roberto Filati srl. Get a sense of the local culture at Cathedral of Santa Maria del Fiore and Castello di Verrazzano. Explore Florence's surroundings by going to Podere Le Ripi (in Montalcino) and Cappella della Madonna di Vitaleta (in San Quirico d'Orcia). Next up on the itinerary: take some stellar pictures from Basilica San Miniato al Monte, take in the architecture and atmosphere at Basilica of Santa Croce, admire the masterpieces at Gallerie Degli Uffizi, and take in the spiritual surroundings of The Baptistery of St. John.

Start your trip to Florence by creating a personalized itinerary on Inspirock.

You can drive from Greve in Chianti to Florence in an hour. Alternatively, you can take a bus. Expect a daytime high around 71°F in October, and nighttime lows around 54°F. Finish your sightseeing early on the 3rd (Sat) so you can drive to Firenzuola.

Things to do in Florence

Historic Sites Tours Museums

Side Trips

San Quirico d'Orcia, Podere Le Ripi, Castello di Verrazzano
Highlights from your plan
San Quirico d'Orcia ©
San Quirico d'Orcia
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Florence Academy of Fine Arts ©
Florence Academy of Fine Arts

1
night
Firenzuola

Firenzuola ©
Firenzuola is a comune (municipality) in the Province of Florence in the Italian region Tuscany, located about 40km northeast of Florence.Firenzuola borders the following municipalities: Barberino di Mugello, Borgo San Lorenzo, Castel del Rio, Castiglione dei Pepoli, Monghidoro, Monterenzio, Palazzuolo sul Senio, San Benedetto Val di Sambro, Scarperia.The medieval jurist Giovanni d'Andrea was born in the frazione of Rifredo around 1270. On the 3rd (Sat), pause for some serene contemplation at Chiesa di San Giovanni Battista, take in the dramatic natural features at Sasso di San Zanobi, identify plant and animal life at Oasi Anpil di Covigliaio, thenexplore the different monuments and memorials at Cimitero Militare Germanico, and finally steep yourself in history at Badia di San Pietro in Moscheta.

To see where to stay, photos, and more tourist information, you can read our Firenzuola online trip planner.

You can drive from Florence to Firenzuola in 1.5 hours. In November, daily temperatures in Firenzuola can reach 61°F, while at night they dip to 45°F. Finish your sightseeing early on the 4th (Sun) so you can drive to Lucca.

Things to do in Firenzuola

Parks Wildlife Historic Sites

Side Trip

Oasi Anpil di Covigliaio
Highlights from your plan
Sasso di San Zanobi ©
Sasso di San Zanobi
Cimitero Militare Germanico ©
Cimitero Militare Germanico
Badia di San Pietro in Moscheta ©
Badia di San Pietro in Moscheta

few
hours
Lucca

Lucca
Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
For other places to visit, where to stay, traveler tips, and tourist information, you can read our Lucca journey planner.

Traveling by car from Firenzuola to Lucca takes 2 hours. November in Lucca sees daily highs of 61°F and lows of 46°F at night. On the 4th (Sun), you're off to Pisa.

Things to do in Lucca

Outdoors Parks Tours

few
hours
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.
To see more things to do, where to stay, other places to visit, and more tourist information, read our Pisa driving holiday planner.

You can drive from Lucca to Pisa in an hour. Other options are to take a bus; or take a train. Expect a daytime high around 61°F in November, and nighttime lows around 46°F. On the 4th (Sun), you're off to Livorno.

Things to do in Pisa

Tours Outdoors Historic Sites

few
hours
Livorno

Livorno
Considered one of Tuscany's newer cities, the busy port city of Livorno boasts modern charm uncharacteristic of the region.
To find where to stay, more things to do, ratings, and other tourist information, use the Livorno trip planner.

You can drive from Pisa to Livorno in an hour. Other options are to take a train; or take a bus. In November, daytime highs in Livorno are 61°F, while nighttime lows are 46°F. On the 4th (Sun), you're off to Siena.

Things to do in Livorno

Outdoors Parks Beaches

1
night
Siena

Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
You've now added Palazzo Pubblico and Museo Civico to your itinerary. On the 5th (Mon), get a sense of history and politics at Palazzo Pubblico and Museo Civico.

To see reviews, maps, traveler tips, and more tourist information, read Siena journey planner.

You can drive from Livorno to Siena in 2 hours. Other options are to take a train; or take a bus. In November, daily temperatures in Siena can reach 63°F, while at night they dip to 48°F. You will have some time to spend on the 5th (Mon) before leaving for Seggiano.

Things to do in Siena

Museums Historic Sites
Highlights from your plan
Palazzo Pubblico and Museo Civico ©
Palazzo Pubblico and Museo Civico

few
hours
Seggiano

Seggiano
Seggiano is a comune (municipality) in the Province of Grosseto in the Italian region Tuscany, located about 100km south of Florence and about 40km northeast of Grosseto.The center is situated on the foothills of the north-western hills of Monte Amiata in a dominating position with respect to the underlying course of the Orcia river and its tributaries, Vivo and Ente.Seggiano borders the following municipalities: Abbadia San Salvatore, Castel del Piano, Castiglione d'Orcia.Near Seggiano is the "Giardino di Daniel Spoerri", a sculpture garden by the artist Daniel Spoerri.TerritoryThe municipality covers an area of less than 50km2, between the north-west slopes of the volcanic massif of Monte Amiata and a section of the Val d'Orcia, the point at which creeps from the province of Siena towards that of Grosseto. For reviews, photos, maps, and other tourist information, read our Seggiano online journey planner.

Traveling by car from Siena to Seggiano takes 1.5 hours. In November, daily temperatures in Seggiano can reach 63°F, while at night they dip to 48°F. You'll set off for Rome on the 5th (Mon).

Things to do in Seggiano

Museums Historic Sites Outdoors

3
nights
Rome

Rome ©
Your day-by-day itinerary now includes Trevi Fountain, Roman Forum, ViniCultural Tours, and other attractions you added. Satisfy your inner culture vulture at Colosseum and Via Condotti. Get some historical perspective at Pantheon and Piazza Navona. See some other sides of Rome: delve into the distant past at Palatine Hill.

Plan my day in Rome using traveler tips and tourist information provided by Inspirock.

You can drive from Seggiano to Rome in 3 hours. Cap off your sightseeing on the 8th (Thu) early enough to travel back home.

Things to do in Rome

Historic Sites Classes Shopping
Highlights from your plan
Piazza Navona ©
Piazza Navona
Pantheon ©
Pantheon
Colosseum ©
Colosseum

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