14 days in Tuscany & Rome Itinerary

14 days in Tuscany & Rome Itinerary

Created using Inspirock Italy tour planner

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Route & dates

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, and shopping. 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, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, and don't miss a visit to Piazzale Michelangelo.

To find reviews, other places to visit, more things to do, and tourist information, go to the Florence trip itinerary maker site.

Toronto, Canada to Florence is an approximately 13- hour flight. You can also do a combination of flight and train; or do a combination of ferry and flight. The time zone changes from Eastern Standard Time (EST) to Central European Standard Time (CET), which is usually a 6 hour difference. Expect a bit warmer temperatures when traveling from Toronto in October; daily highs in Florence reach 25°C and lows reach 14°C. Wrap up your sightseeing on the 11th (Sun) to allow time to take a bus to Lucca.

Things to do in Florence

Historic Sites Museums Tours
Find places to stay Oct 8 — 11:
Highlights from your plan
Food Tours
Gallerie Degli Uffizi ©
Gallerie Degli Uffizi
Piazzale Michelangelo ©
Piazzale Michelangelo

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 12th (Mon): explore the different monuments and memorials at Camposanto, steep yourself in history at Le mura di Lucca, don't miss a visit to Piazza Anfiteatro, take in panoramic vistas at Torre Guinigi, then appreciate the extensive heritage of Santuario di Santa Gemma Galgani, and finally take in the spiritual surroundings of San Michele in Foro. On the 13th (Tue), you'll have a packed day of sightseeing: contemplate the long history of Baptistery of St. John, make a trip to Leaning Tower of Pisa, and then contemplate in the serene atmosphere at Duomo di Pisa.

To see more things to do, photos, traveler tips, and other tourist information, use the Lucca trip 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. Finish your sightseeing early on the 13th (Tue) to allow enough time to drive 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
Torre Guinigi ©
Torre Guinigi

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 take in the exciting artwork at La Bottega del Sale di Duccio Nacci photographer. Get ready for a full day of sightseeing on the 14th (Wed): learn about winemaking at Guardastelle Vineyard, contemplate the long history of Historic Centre of San Gimignano, and then take in the architecture and atmosphere at Duomo di San Gimignano.

To see other places to visit, traveler tips, more things to do, and other tourist information, read our San Gimignano tour itinerary planner.

Traveling by car from Lucca to San Gimignano takes 2 hours. Alternatively, you can do a combination of train and bus; or take a bus. Expect a daytime high around 25°C in October, and nighttime lows around 14°C. Finish your sightseeing early on the 15th (Thu) so you can 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
Guardastelle Vineyard ©
Guardastelle Vineyard
Historic Centre of San Gimignano ©
Historic Centre of San Gimignano
Duomo di San Gimignano ©
Duomo di San Gimignano

2
nights
Siena

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 16th (Fri), indulge your senses at some of the top wineries in the area, browse the collection at Biblioteca Piccolomini, and then take in panoramic vistas at Torre del Mangia. On the next day, indulge in some culinary diversions at a local gastronomic tour, then pause for some serene contemplation at Duomo di Siena, and then make a trip to Piazza del Campo.

To see where to stay, ratings, other places to visit, and other tourist information, use the Siena travel route builder.

Drive from San Gimignano to Siena in an hour. Alternatively, you can take a bus; or do a combination of bus and train. In October, plan for daily highs up to 26°C, and evening lows to 15°C. Wrap up your sightseeing on the 17th (Sat) to allow time 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.
On the 18th (Sun), do a tasting at Azienda Agricola Leuta, don't miss a visit to Piazza della Repubblica, then examine the collection 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. On your second day here, don't miss a visit to Piazza Grande a Montepulciano, savor the flavors at Food & Drink, and then look for gifts at Silvia Taccola Vanni - Laboratorio Stilistico.

To see traveler tips, other places to visit, photos, and other tourist information, read Cortona road trip planning app.

You can drive from Siena to Cortona in 1.5 hours. Alternatively, you can do a combination of bus and train; or take a train. Finish your sightseeing early on the 19th (Mon) to allow enough time to drive to Rome.

Things to do in Cortona

Tours Museums Historic Sites

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.
On the 20th (Tue), contemplate the long history of Colosseum, contemplate in the serene atmosphere at Chiesa di Sant'Ignazio di Loyola, then steep yourself in history at St. Peter's Basilica, then take in the architecture and atmosphere at Pantheon, and finally don't miss a visit to Trevi Fountain. On your second day here, admire the masterpieces at Vatican Museums and then pause for some serene contemplation at Santa Maria in Trastevere.

To find where to stay, other places to visit, maps, and other tourist information, read Rome online route planner.

Drive from Cortona to Rome in 2.5 hours. Alternatively, you can take a train. In October in Rome, expect temperatures between 26°C during the day and 15°C at night. Finish your sightseeing early on the 21st (Wed) to allow enough time to 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
Trevi Fountain ©
Trevi Fountain
St. Peter's Basilica ©
St. Peter's Basilica

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