9 days in Tuscany Itinerary

9 days in Tuscany Itinerary

Created using Inspirock Tuscany tour planner
Make it your trip
Fly
1
Siena
— 2 nights
Drive
2
Montepulciano
— 1 night
Drive
3
Cortona
Drive
4
Montepulciano
— 1 night
Taxi
5
Chianciano Terme
Drive
6
Pienza
Drive
7
Bagno Vignoni
Drive
8
Montepulciano
— 1 night
Drive
9
Volterra
— 2 nights
Drive
10
San Gimignano
— 1 night
Drive

S M T W T F S
18
19
20
21
22
23
24
25
26
27
28
29
30
1

Siena — 2 nights

Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 20th (Tue), take in the architecture and atmosphere at Duomo di Siena and then indulge your senses at some of the top wineries in the area.

For photos, reviews, ratings, and more tourist information, go to the Siena day trip planner.

Toronto, Canada to Siena is an approximately 13.5-hour flight. The time zone difference moving from Eastern Standard Time (EST) to Central European Standard Time (CET) is 6 hours. When traveling from Toronto in September, plan for a bit warmer days and about the same nights in Siena: temperatures range from 32°C by day to 19°C at night. You will have some time to spend on the 21st (Wed) before leaving for Montepulciano.
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Tours · Wineries · Historic Sites
Find places to stay Sep 19 — 21:

Montepulciano — 1 night

Perched on a limestone ridge in the heart of Tuscany, Montepulciano is known worldwide for its production of red wine, the Vino Noble.
Kick off your visit on the 21st (Wed): learn about winemaking at De' Ricci, do a tasting at Avignonesi, and then contemplate in the serene atmosphere at Tempio di San Biagio.

To see ratings, more things to do, other places to visit, and more tourist information, read our Montepulciano day trip planner.

Traveling by car from Siena to Montepulciano takes an hour. Alternatively, you can take a train; or take a bus. In September, daytime highs in Montepulciano are 32°C, while nighttime lows are 19°C. Cap off your sightseeing on the 22nd (Thu) early enough to go by car to Cortona.
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Wineries · Historic Sites
Find places to stay Sep 21 — 22:
Highlights from your trip

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.
Kick off your visit on the 22nd (Thu): take in the architecture and atmosphere at Santa Margherita, Cortona, then see the interesting displays at Museo Diocesano, then take an in-depth tour of MAEC - Museo dell'Accademia Etrusca, and finally look for gifts at DelBrenna Jewelry.

To find more things to do, other places to visit, ratings, and tourist information, use the Cortona trip builder app.

Traveling by car from Montepulciano to Cortona takes an hour. Alternatively, you can take a train; or take a bus. Finish up your sightseeing early on the 22nd (Thu) so you can go by car to Montepulciano.
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Historic Sites · Museums · Shopping
Find places to stay Sep 22 — 23:

Montepulciano — 1 night

On the 22nd (Thu), make a trip to Terrazza Del Palazzo Comunale and then don't miss a visit to Piazza Grande a Montepulciano.

To see reviews, more things to do, photos, and tourist information, go to the Montepulciano online journey planner.

You can drive from Cortona to Montepulciano in an hour. Other options are to take a train; or take a bus. Finish your sightseeing early on the 23rd (Fri) so you can drive to Chianciano Terme.
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Find places to stay Sep 22 — 23:

Chianciano Terme

Chianciano Terme is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 90km southeast of Florence and about 50km southeast of Siena. Kick off your visit on the 23rd (Fri): look for gifts at Il Granaio di Gabriello.

To find ratings, traveler tips, maps, and other tourist information, you can read our Chianciano Terme road trip planner.

Chianciano Terme is very close to Montepulciano. In September, plan for daily highs up to 32°C, and evening lows to 19°C. On the 23rd (Fri), you'll have the morning to explore before heading off to Pienza.
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Shopping
Side Trip
Find places to stay Sep 23 — 24:
Highlights from your trip

Pienza

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. For ratings, where to stay, traveler tips, and more tourist information, you can read our Pienza road trip planning tool.

Pienza is just a short distance from Chianciano Terme. In September, daily temperatures in Pienza can reach 32°C, while at night they dip to 19°C. On the 23rd (Fri), you'll travel to Bagno Vignoni.
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Wineries · Historic Sites · Tours · Outdoors
Find places to stay Sep 23 — 24:

Bagno Vignoni

Start off your visit on the 23rd (Fri): don't miss a visit to Terme Bagno Vignoni, then don't miss a visit to Piscina Termale, and then witness a stunning natural landmark at Parco dei Mulini.

For more things to do, traveler tips, photos, and other tourist information, use the Bagno Vignoni online driving holiday planner.

Bagno Vignoni is just a short distance from Pienza. In September in Bagno Vignoni, expect temperatures between 32°C during the day and 19°C at night. Finish your sightseeing early on the 23rd (Fri) to allow enough time to drive to Montepulciano.
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Historic Sites · Parks · Nature
Find places to stay Sep 23 — 24:
Highlights from your trip

Montepulciano — 1 night

To see more things to do, ratings, photos, and other tourist information, read Montepulciano trip planner.

Traveling by car from Bagno Vignoni to Montepulciano takes an hour. On the 24th (Sat), you'll travel to Volterra.
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Historic Sites · Wineries · Tours · Outdoors
Find places to stay Sep 23 — 24:

Volterra — 2 nights

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. Take a break from Volterra with a short trip to Cavallino Matto in Marina di Castagneto Carducci, about 54 minutes away. There's much more to do: explore the historical opulence of Palazzo dei Priori, take in the architecture and atmosphere at Cathedral of Santa Maria Assunta, contemplate the long history of Piazza dei Priori, and explore the ancient world of Porta all'Arco.

For traveler tips, where to stay, other places to visit, and tourist information, read Volterra trip planning tool.

Drive from Montepulciano to Volterra in 2 hours. Alternatively, you can do a combination of train and taxi; or take a bus. In September, daytime highs in Volterra are 30°C, while nighttime lows are 17°C. Finish your sightseeing early on the 26th (Mon) so you can drive to San Gimignano.
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Historic Sites · Theme Parks · Museums · Shopping
Side Trip
Find places to stay Sep 24 — 26:

San Gimignano — 1 night

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 26th (Mon), steep yourself in history at Historic Centre of San Gimignano.

To see more things to do, reviews, photos, and more tourist information, read San Gimignano trip planner.

Traveling by car from Volterra to San Gimignano takes an hour. In September, plan for daily highs up to 30°C, and evening lows to 17°C. You'll have a few hours on the 27th (Tue) to wrap things up before traveling home.
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Historic Sites
Find places to stay Sep 26 — 27:

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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