6 days in Tuscany Itinerary

Created using Inspirock Tuscany trip itinerary planner
Make it your trip
Fly
1
Greve in Chianti
Drive
2
Pienza
— 1 night
Drive
3
San Gimignano
— 2 nights
Drive
4
Radda in Chianti
Drive
5
Florence
— 1 night
Drive
6
Siena
— 1 night
Fly

S M T W T F S
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Greve in Chianti

On the 6th (Wed), do a tasting at Montefioralle Winery.

For more things to do, reviews, traveler tips, and other tourist information, use the Greve in Chianti driving holiday planner.

London, UK to Greve in Chianti is an approximately 5.5-hour flight. You can also do a combination of train and bus; or drive. The time zone difference when traveling from London to Greve in Chianti is 1 hour. Plan for somewhat warmer temperatures traveling from London in September, with highs in Greve in Chianti at 30°C and lows at 17°C. Wrap up your sightseeing by early afternoon on the 6th (Wed) to allow enough time to drive to Pienza.
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Wineries
Find places to stay Sep 6 — 7:

Pienza — 1 night

Pienza, a town and comune in the province of Siena, in the Val d'Orcia in Tuscany (central Italy), between the towns of Montepulciano and Montalcino, is the "touchstone of Renaissance urbanism."In 1996, UNESCO declared the town a World Heritage Site, and in 2004 the entire valley, the Val d'Orcia, was included on the list of UNESCO's World Cultural Landscapes.HistoryBefore the village was renamed to Pienza its name was Corsignano. On the 6th (Wed), don't miss a visit to Piazza Grande a Montepulciano and then take in the spiritual surroundings of Tempio di San Biagio.

For more things to do, photos, where to stay, and other tourist information, read our Pienza holiday planner.

You can drive from Greve in Chianti to Pienza in 2 hours. Other options are to take a bus; or do a combination of bus and train. Expect a daytime high around 32°C in September, and nighttime lows around 19°C. Finish up your sightseeing early on the 7th (Thu) so you can go by car to San Gimignano.
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Historic Sites · Shopping · Museums
Side Trips
Find places to stay Sep 6 — 7:

San Gimignano — 2 nights

Town of Fine Towers

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 8th (Fri), appreciate the extensive heritage of Piazza del Duomo, make a trip to Piazza della Cisterna, contemplate the long history of Torre e Casa Campatelli, then explore the galleries of San Gimignano 1300, then learn about winemaking at Podere La Marronaia- Le Colonne Biodynamic Winery & Farm, and finally learn about winemaking at Azienda Agricola San Quirico.

To see other places to visit, traveler tips, maps, and more tourist information, you can read our San Gimignano day trip planning app.

Getting from Pienza to San Gimignano by car takes about 2 hours. Other options: do a combination of bus and train; or take a bus. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. On the 9th (Sat), you'll have the morning to explore before heading off to Radda in Chianti.
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Historic Sites · Wineries · Museums
Find places to stay Sep 7 — 9:

Radda in Chianti

Kick off your visit on the 9th (Sat): do a tasting at Castello San Donato in Perano and then learn about winemaking at Poggio Amorelli.

For traveler tips, more things to do, other places to visit, and tourist information, you can read our Radda in Chianti online travel route planner.

Getting from San Gimignano to Radda in Chianti by car takes about an hour. Other options: do a combination of train and bus; or take a bus. In September, daily temperatures in Radda in Chianti can reach 31°C, while at night they dip to 17°C. Wrap up your sightseeing on the 9th (Sat) early enough to drive to Florence.
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Wineries
Side Trip
Find places to stay Sep 9 — 10:

Florence — 1 night

Birthplace of the Italian Renaissance

Considered a cultural, artistic, and architectural jewel of Italy, Florence is the birthplace of the Italian Renaissance.
On the 9th (Sat), get to know the fascinating history of Piazza del Duomo.

For ratings, traveler tips, other places to visit, and other tourist information, read Florence day trip planning app.

Drive from Radda in Chianti to Florence in 1.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. In September in Florence, expect temperatures between 30°C during the day and 17°C at night. Finish your sightseeing early on the 10th (Sun) to allow enough time to drive to Siena.
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Historic Sites · Museums
Find places to stay Sep 9 — 10:

Siena — 1 night

Cultural Heart of Tuscany

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 11th (Mon): take in the architecture and atmosphere at Duomo di Siena, then take in panoramic vistas at Torre del Mangia, then admire the masterpieces at Complesso Museale Santa Maria della Scala, and finally don't miss a visit to Centro Storico di Siena.

To find traveler tips, other places to visit, reviews, and more tourist information, you can read our Siena trip itinerary app.

Traveling by car from Florence to Siena takes 1.5 hours. Alternatively, you can take a bus; or take a train. In September, daily temperatures in Siena can reach 32°C, while at night they dip to 19°C. Wrap up your sightseeing on the 11th (Mon) to allow time to fly back home.
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Historic Sites · Museums
Find places to stay Sep 10 — 11:

Tuscany travel guide

4.4
Landmarks · Art Museums · Sacred & Religious Sites
Birthplace of the Italian Renaissance
Known for its landscapes, traditions, and history, Tuscany possesses an unparalleled artistic legacy that continues to influence world culture. Regarded as the birthplace of the Italian Renaissance, the region boasts a lengthy list of attractions, including world-class museums, art galleries, and archeological sites. With a distinct culture and a very strong linguistic identity, this region is sometimes referred to as a nation within a nation. A land of picture-postcard areas, Tuscany contains plenty of places to visit on your holiday, with seven World Heritage Sites, including the historic town centers of Florence and Siena. With more than 120 protected nature preserves, Tuscany is not only a land of culture and historic monuments, but also a great place to discover and enjoy the Italian outdoors. Take it slowly here (as the locals do), and give yourself plenty of time to get to know the local culture and cuisine of Tuscany's medieval towns and ancient villages.
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