14 days in Tuscany & Rome Itinerary

14 days in Tuscany & Rome Itinerary

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Route & dates

14 days in Tuscany & Rome Itinerary

Start: Toronto
Fly:  13​h
1
Florence
— 2 nights
bus:  1​h 15​min
2
Lucca
— 2 nights
Drive:  1​h 45​min
3
San Gimignano
— 2 nights
Drive:  1​h
4
Siena
— 2 nights
Drive:  1​h 15​min
5
Cortona
— 2 nights
Drive:  2​h 15​min
6
Rome
— 2 nights
Fly:  12​h 30​min
End: Toronto

2
nights
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, get to know the fascinating history of Piazza del Duomo, snap pictures at Ponte Vecchio, and appreciate the history behind Campanile di Giotto.

For more things to do, other places to visit, where to stay, and tourist information, read Florence trip planning website .

Toronto, Canada to Florence is an approximately 13-hour flight. You can also do a combination of flight and train. The time zone difference moving from Eastern Standard Time to Central European Time is 6 hours. Traveling from Toronto in October, things will get a bit warmer in Florence: highs are around 25°C and lows about 14°C. Wrap up your sightseeing on the 11th (Sun) early enough to take a train to Cortona.

Things to do in Florence

Museums Historic Sites Tours
Find places to stay Oct 8 — 11:
Highlights from your plan
Food Tours
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Academy Of Florence Art Gallery ©
Academy Of Florence Art Gallery

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.
Start off your visit on the 12th (Mon): stroll the grounds of Camposanto, don't miss a visit to Le mura di Lucca, don't miss a visit to Piazza Anfiteatro, then enjoy breathtaking views from Torre Guinigi, then take in the spiritual surroundings of Santuario di Santa Gemma Galgani, and finally take in the spiritual surroundings of San Michele in Foro. Keep things going the next day: take in the spiritual surroundings of Battistero, don't miss a visit to Leaning Tower of Pisa, and then take in the spiritual surroundings of Duomo di Pisa.

For maps, traveler tips, ratings, and other tourist information, read our Lucca trip itinerary planner.

Traveling by bus from Florence to Lucca takes 1.5 hours. Alternatively, you can drive; or take a train. In October, daily temperatures in Lucca can reach 25°C, while at night they dip to 14°C. Cap off your sightseeing on the 13th (Tue) early enough to go by car to San Gimignano.

Things to do in Lucca

Historic Sites

Side Trip

Pisa
Find places to stay Oct 11 — 13:
Highlights from your plan
Le mura di Lucca ©
Le mura di Lucca
Leaning Tower of Pisa ©
Leaning Tower of Pisa
St Martin Cathedral ©
St Martin Cathedral

2
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.
On the 13th (Tue), take an in-depth tour of Torre e Casa Campatelli and then view the masterpieces at La Bottega del Sale di Duccio Nacci photographer. Here are some ideas for day two: do a tasting at Guardastelle Vineyard, then contemplate the long history of Historic Centre of San Gimignano, and then pause for some serene contemplation at Duomo di San Gimignano.

You can plan San Gimignano trip in no time by asking Inspirock to help create your itinerary.

You can drive from Lucca to San Gimignano in 2 hours. Alternatively, you can take a train; or take a bus. In October in San Gimignano, expect temperatures between 25°C during the day and 14°C at night. Wrap up your sightseeing on the 15th (Thu) to allow time to drive to Siena.

Things to do in San Gimignano

Historic Sites Wineries Museums

Side Trip

Walls of Monteriggioni
Find places to stay Oct 13 — 15:
Highlights from your plan
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Duomo di San Gimignano ©
Duomo di San Gimignano
Torre Grossa ©
Torre Grossa

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
Kick off your visit on the 16th (Fri): savor the flavors at Food & Drink, get lost in a book at Biblioteca Piccolomini, and then take in panoramic vistas at Torre del Mangia. On your second day here, let your taste buds guide you at a local gastronomic tour, take in the architecture and atmosphere at Duomo di Siena, and then make a trip to Piazza del Campo.

To see traveler tips, reviews, where to stay, and more tourist information, read Siena day trip planner .

Getting from San Gimignano to Siena by car takes about an hour. Other options: take a bus; or do a combination of bus and train. In October, daily temperatures in Siena can reach 26°C, while at night they dip to 15°C. Wrap up your sightseeing on the 17th (Sat) early enough to drive to Cortona.

Things to do in Siena

Tours Historic Sites
Find places to stay Oct 15 — 17:
Highlights from your plan
Wine Tours & Tastings
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena

2
nights
Cortona

Cortona ©
The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
Start off your visit on the 18th (Sun): learn about winemaking at Azienda Agricola Leuta, don't miss a visit to Piazza della Repubblica, then see the interesting displays at Museo Diocesano, then take an in-depth tour of MAEC - Museo dell'Accademia Etrusca, and finally contemplate in the serene atmosphere at Eremo Le Celle. Get ready for a full day of sightseeing on the 19th (Mon): make a trip to Piazza Grande a Montepulciano, awaken your taste buds at some of the top wineries in the area, and then stop by Silvia Taccola Vanni - Laboratorio Stilistico.

Take the guesswork out of planning a Cortona vacation by using our trip itinerary maker.

Getting from Siena to Cortona by car takes about 1.5 hours. Other options: do a combination of bus and train; or take a train. Cap off your sightseeing on the 19th (Mon) early enough to go by car to Rome.

Things to do in Cortona

Tours Historic Sites Wineries

Side Trip

Piazza Grande a Montepulciano
Find places to stay Oct 17 — 19:
Highlights from your plan
Azienda Agricola Leuta ©
Azienda Agricola Leuta
Museo Diocesano ©
Museo Diocesano
Eremo Le Celle ©
Eremo Le Celle

2
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 20th (Tue): delve into the distant past at Colosseum, contemplate in the serene atmosphere at Chiesa di Sant'Ignazio di Loyola, then pause for some serene contemplation at St. Peter's Basilica, then delve into the distant past at Pantheon, and finally ponder the design of Trevi Fountain. On the next day, explore the world behind art at Vatican Museums and then take in the architecture and atmosphere at Santa Maria in Trastevere.

For where to stay, traveler tips, ratings, and more tourist information, refer to the Rome online travel route planner .

Drive from Cortona to Rome in 2.5 hours. Alternatively, you can take a train. In October, daily temperatures in Rome can reach 26°C, while at night they dip to 15°C. Finish your sightseeing early on the 21st (Wed) so you can travel back home.

Things to do in Rome

Historic Sites Museums

Side Trip

Vatican City
Find places to stay Oct 19 — 21:
Highlights from your plan
Colosseum ©
Colosseum
Pantheon ©
Pantheon
St. Peter's Basilica ©
St. Peter's Basilica

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