12 days in Tuscany Itinerary

12 days in Tuscany Itinerary

Created using Inspirock Italy holiday planner
Make it your trip
1
Grosseto
— 1 night
Drive
2
Montalcino
Drive
3
Pienza
— 1 night
Drive
4
Montepulciano
— 1 night
Drive
5
Siena
— 1 night
Drive
6
San Gimignano
— 1 night
Drive
7
Volterra
Drive
8
San Miniato
— 1 night
Drive
9
Pisa
— 1 night
Drive
10
Lucca
Drive
11
Greve in Chianti
— 3 nights
Drive
12
Florence
— 1 night

S M T W T F S
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Grosseto — 1 night

Grosseto is a city and comune in the central Italian region of Tuscany, the capital of the Province of Grosseto. On the 6th (Mon), stroll through Marina di Alberese, contemplate in the serene atmosphere at Duomo di San Lorenzo, and then appreciate the extensive heritage of Piazza Dante.

To see more things to do, where to stay, maps, and more tourist information, you can read our Grosseto trip planner.

If you are flying in from Germany, the closest major aiports are Peretola Airport, Pisa International Airport and Perugia San Francesco d'Assisi – Umbria International Airport. In September, daytime highs in Grosseto are 32°C, while nighttime lows are 19°C. Finish your sightseeing early on the 7th (Tue) so you can drive to Montalcino.
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Historic Sites · Parks · Beaches · Outdoors
Find places to stay Sep 6 — 7:
Highlights from your trip

Montalcino

City of Honey

In the heart of wine country, the hill town of Montalcino offers a glimpse of untouched medieval-era Tuscany.
To see where to stay, photos, maps, and other tourist information, read Montalcino travel route planner.

Drive from Grosseto to Montalcino in an hour. Alternatively, you can take a bus; or do a combination of train and bus. In September, daily temperatures in Montalcino can reach 32°C, while at night they dip to 19°C. On the 7th (Tue), you're off to Pienza.
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Historic Sites · Wineries · Tours · Shopping
Find places to stay Sep 7 — 8:

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. Kick off your visit on the 7th (Tue): appreciate the extensive heritage of San Quirico d'Orcia, contemplate the long history of Terme Bagno Vignoni, then stop by La Taverna del Pecorino, and finally don't miss a visit to Piazza Pio II.

To see other places to visit, more things to do, traveler tips, and tourist information, read Pienza holiday site.

Pienza is just a stone's throw from Montalcino. September in Pienza sees daily highs of 32°C and lows of 19°C at night. Finish up your sightseeing early on the 8th (Wed) so you can go by car to Montepulciano.
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Historic Sites · Shopping
Side Trips
Find places to stay Sep 7 — 8:

Montepulciano — 1 night

Pearl of the 16th Century

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 8th (Wed): do a tasting at Avignonesi, indulge in some personalized pampering at some of the best spas, then make a trip to Piazza Grande a Montepulciano, and finally take in the spiritual surroundings of Tempio di San Biagio.

To find other places to visit, reviews, more things to do, and tourist information, use the Montepulciano journey site.

Montepulciano is just a short distance from Pienza. In September, daytime highs in Montepulciano are 32°C, while nighttime lows are 19°C. Cap off your sightseeing on the 9th (Thu) early enough to go by car to Siena.
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Wineries · Spas · Historic Sites
Side Trip
Find places to stay Sep 8 — 9:

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.
Kick off your visit on the 9th (Thu): get a sense of history and politics at Palazzo Pubblico and Museo Civico, don't miss a visit to Piazza del Campo, and then indulge your senses at some of the top wineries in the area.

To see maps, photos, where to stay, and more tourist information, you can read our Siena sightseeing planner.

Traveling by car from Montepulciano to Siena takes an hour. Alternatively, you can take a train; or take a bus. In September, daytime highs in Siena are 32°C, while nighttime lows are 19°C. Wrap up your sightseeing on the 10th (Fri) early enough to drive to San Gimignano.
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Tours · Wineries · Historic Sites · Museums
Find places to stay Sep 9 — 10:

San Gimignano — 1 night

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.
Start off your visit on the 10th (Fri): learn about winemaking at Podere La Marronaia- Sosta Alle Colonne, then learn about winemaking at Guardastelle Vineyard, then steep yourself in history at Historic Centre of San Gimignano, and finally pause for some serene contemplation at Duomo di San Gimignano.

To see traveler tips, other places to visit, maps, and more tourist information, refer to the San Gimignano route website.

Getting from Siena to San Gimignano by car takes about an hour. Other options: take a train; or take a bus. Expect a daytime high around 30°C in September, and nighttime lows around 17°C. Finish your sightseeing early on the 11th (Sat) so you can drive to Volterra.
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Wineries · Historic Sites
Find places to stay Sep 10 — 11:

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. Planning Volterra trip won't be overwhelming when you use Inspirock's itinerary maker.

You can drive from San Gimignano to Volterra in an hour. In September, daytime highs in Volterra are 30°C, while nighttime lows are 17°C. You will leave for San Miniato on the 11th (Sat).
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Outdoors · Historic Sites · Parks · Tours
Find places to stay Sep 11 — 12:

San Miniato — 1 night

San Miniato is a town and comune in the province of Pisa, in the region of Tuscany, Italy.San Miniato sits at an historically strategic location atop three small hills where it dominates the lower Arno valley between the valleys of Egola and Elsa. On the 11th (Sat), make a trip to Tower of Federico II and then do a tasting at Cosimo Maria Masini.

For ratings, more things to do, photos, and more tourist information, you can read our San Miniato trip itinerary planning tool.

Traveling by car from Volterra to San Miniato takes an hour. Alternatively, you can drive. In September, daily temperatures in San Miniato can reach 30°C, while at night they dip to 17°C. Finish up your sightseeing early on the 12th (Sun) so you can go by car to Pisa.
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Wineries
Find places to stay Sep 11 — 12:

Pisa — 1 night

Known worldwide for the Leaning Tower of Pisa, the city of Pisa historically served as a maritime power in the heart of Tuscany.
On the 12th (Sun), contemplate in the serene atmosphere at Battistero di San Giovanni, don't miss a visit to Piazza dei Miracoli, and then take in panoramic vistas at Leaning Tower of Pisa. Get ready for a full day of sightseeing on the 13th (Mon): appreciate the extensive heritage of Knights’ Square, take in the spiritual surroundings of Duomo di Pisa, and then explore the different monuments and memorials at Camposanto.

To see ratings, more things to do, traveler tips, and more tourist information, use the Pisa online tour itinerary planner.

Getting from San Miniato to Pisa by car takes about an hour. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Wrap up your sightseeing on the 13th (Mon) to allow time to drive to Lucca.
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Historic Sites
Find places to stay Sep 12 — 13:

Lucca

City of a Hundred Churches

Lucca, famous for its intact Renaissance-era city walls, remained an independent city-state until the end of the 18th century.
To see other places to visit, maps, photos, and more tourist information, go to the Lucca trip itinerary planning app.

Lucca is just a short distance from Pisa. September in Lucca sees daily highs of 30°C and lows of 17°C at night. You'll set off for Greve in Chianti on the 13th (Mon).
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Outdoors · Historic Sites · Tours · Parks
Find places to stay Sep 13 — 14:

Greve in Chianti — 3 nights

Change things up with these side-trips from Greve in Chianti: Poggio Amorelli (in Castellina In Chianti) and Fattoria Casa Sola (in Barberino Val d'Elsa).

Before you visit Greve in Chianti, use our trip planner to discover what you can do and see there.

Drive from Lucca to Greve in Chianti in 1.5 hours. Alternatively, you can do a combination of train and bus; or take a bus. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Finish your sightseeing early on the 16th (Thu) to allow enough time to drive to Florence.
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Wineries · Historic Sites
Side Trips
Find places to stay Sep 13 — 16:

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 17th (Fri), make a trip to Piazza della Signoria, contemplate in the serene atmosphere at Cathedral of Santa Maria del Fiore, enjoy breathtaking views from Campanile di Giotto, don't miss a visit to Piazzale Michelangelo, then snap pictures at Ponte Vecchio, and finally admire the masterpieces at Florence Academy of Fine Arts.

To see where to stay, ratings, reviews, and more tourist information, refer to the Florence trip itinerary builder website.

You can drive from Greve in Chianti to Florence in an hour. Alternatively, you can take a bus. In September, plan for daily highs up to 30°C, and evening lows to 17°C. Cap off your sightseeing on the 17th (Fri) early enough to travel back home.
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Historic Sites · Museums
Find places to stay Sep 16 — 17:

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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