📍 Italy

SIENA PROVINCE: 20 MEDIEVAL VILLAGES AND TUSCAN SOUL

Stone ramparts ringing medieval villages, Chianti slopes cradling wine tradition, brick towers crowning hills. Siena, timeless.

≈ 19
Days
265
Km
18
Stops
📖 10 min read 🔄 Last updated: 2026-01-17

Circle Monteriggioni's round ramparts, then explore Castellina and its wine-country fortifications. Approach Radda's cellars, observe Poggibonsi and its medieval past, discover Colle Val d'Elsa and its crystal, cross Casole and find Sovicille's monastic calm. Sienese villages express a sincere preserved Tuscany.

Your day-by-day itinerary

1
Day

Monteriggioni

fortress village wall crown

Monteriggioni - Photo 1Monteriggioni - Photo 2Monteriggioni - Photo 3Monteriggioni - Photo 4Monteriggioni - Photo 5Monteriggioni - Photo 6
6 photos
Day 1
🔍

Discover

1
Medieval fortified enclosure (570 m long, 2 m high)
2
Historic center of Chianti Senese
🎯

Activities

→
Walk on the ramparts
🚗
Next stop
Distance: 13 km
Travel time: 16min
2
Day

Castellina In Chianti

Chianti fortress wine gateway

Castellina In Chianti - Photo 1Castellina In Chianti - Photo 2Castellina In Chianti - Photo 3Castellina In Chianti - Photo 4Castellina In Chianti - Photo 5Castellina In Chianti - Photo 6
6 photos
Day 2
🔍

Discover

1
Strategic position between Chianti Senese and Colli Fiorentini
2
Fortified borgo on hill
🎯

Activities

→
Discovery of the Chianti wine region
🚗
Next stop
Distance: 10 km
Travel time: 11min
3
Day

Radda In Chianti

wine cellars valley sanctuary

Radda In Chianti - Photo 1Radda In Chianti - Photo 2Radda In Chianti - Photo 3Radda In Chianti - Photo 4Radda In Chianti - Photo 5Radda In Chianti - Photo 6Radda In Chianti - Photo 7
7 photos
Day 3
🔍

Discover

1
Preserved medieval palaces
2
Former ice houses transformed into exhibition spaces
3
Rocca di Staggia (fortress)
🎯

Activities

→
Historic defensive walls
🚗
Next stop
Distance: 24 km
Travel time: 28min
4
Day

Poggibonsi

medieval village strategic post

Poggibonsi - Photo 1Poggibonsi - Photo 2Poggibonsi - Photo 3Poggibonsi - Photo 4Poggibonsi - Photo 5Poggibonsi - Photo 6
6 photos
Day 4
🔍

Discover

1
Castello Magione (Templar origin)
2
Archaeological Park of Poggibonsi
3
Historic center on high ground
🎯

Activities

→
One of the most important archaeological parks in Italy
🚗
Next stop
Distance: 7 km
Travel time: 9min
5
Day

Colle Val Elsa

crystal tradition artisan heritage

Colle Val Elsa - Photo 1Colle Val Elsa - Photo 2Colle Val Elsa - Photo 3Colle Val Elsa - Photo 4Colle Val Elsa - Photo 5Colle Val Elsa - Photo 6Colle Val Elsa - Photo 7Colle Val Elsa - Photo 8
8 photos
Day 5
🔍

Discover

1
Italian capital of crystal
2
Crystal shops and workshops
3
Historic center with medieval alleyways
🎯

Activities

→
San Gimignano (14 medieval towers - UNESCO)
→
Cathedral with frescoes
→
Panorama over the Val d'Elsa
🚗
Next stop
Distance: 14 km
Travel time: 17min
6
Day

Casole Elsa

ancient heritage site Etruscan

Casole Elsa - Photo 1Casole Elsa - Photo 2Casole Elsa - Photo 3Casole Elsa - Photo 4Casole Elsa - Photo 5Casole Elsa - Photo 6Casole Elsa - Photo 7Casole Elsa - Photo 8Casole Elsa - Photo 9Casole Elsa - Photo 10
10 photos
Day 6
🔍

Discover

1
Oval-shaped walls
2
Medieval churches and palaces
3
Village of the Montagnola Senese
🎯

Activities

→
Site marked by medieval history
🚗
Next stop
Distance: 21 km
Travel time: 26min
7
Day

Sovicille

monastery peace spiritual refuge

Sovicille - Photo 1Sovicille - Photo 2Sovicille - Photo 3Sovicille - Photo 4Sovicille - Photo 5Sovicille - Photo 6
6 photos
Day 7
🔍

Discover

1
Historic underground passages beneath the main square
2
Two local museums
🎯

Activities

→
Emblematic cypresses of the region
🚗
Next stop
Distance: 36 km
Travel time: 43min
8
Day

Asciano

clay landscape valley crete

Asciano - Photo 1Asciano - Photo 2Asciano - Photo 3Asciano - Photo 4Asciano - Photo 5Asciano - Photo 6
6 photos
Day 8
🔍

Discover

1
Historic palaces
2
Iconic landscapes of the Crete Senesi
3
Medieval fortified walls
🎯

Activities

→
Preserved historic center
🚗
Next stop
Distance: 16 km
Travel time: 20min
9
Day

Buonconvento

riverside village terra cotta

Buonconvento - Photo 1Buonconvento - Photo 2Buonconvento - Photo 3Buonconvento - Photo 4Buonconvento - Photo 5Buonconvento - Photo 6Buonconvento - Photo 7Buonconvento - Photo 8
8 photos
Day 9
🔍

Discover

1
Two historic entrance gates
2
Narrow streets, palaces and churches
3
Historic center of the Crete Senesi
🎯

Activities

→
Cypress and hill landscapes
🚗
Next stop
Distance: 11 km
Travel time: 14min
10
Day

Montalcino

wine fortress hilltop jewel

Montalcino - Photo 1Montalcino - Photo 2Montalcino - Photo 3Montalcino - Photo 4Montalcino - Photo 5Montalcino - Photo 6
6 photos
Day 10
🔍

Discover

1
Medieval alleyways
2
Capital of Brunello di Montalcino
3
Village of Val d'Orcia (UNESCO)
🎯

Activities

→
Thermal establishments in the surroundings
🚗
Next stop
Distance: 12 km
Travel time: 15min
11
Day

San Quirico Orcia

thermal gateway valley threshold

San Quirico Orcia - Photo 1San Quirico Orcia - Photo 2San Quirico Orcia - Photo 3San Quirico Orcia - Photo 4San Quirico Orcia - Photo 5San Quirico Orcia - Photo 6
6 photos
Day 11
🔍

Discover

1
Stop on the Via Francigena
2
Bagno Vignoni (central thermal pool)
3
Renaissance historic center (Bernardo Rossellino)
🎯

Activities

→
Renaissance architecture
→
Hiking trails
🚗
Next stop
Distance: 8 km
Travel time: 10min
12
Day

Pienza

Renaissance palace village gem

Pienza - Photo 1Pienza - Photo 2Pienza - Photo 3Pienza - Photo 4Pienza - Photo 5Pienza - Photo 6
6 photos
Day 12
🔍

Discover

1
15th-century urban planning masterpiece
2
Pecorino cheese capital
3
Fortress visible for kilometers
🎯

Activities

→
Palio del Bigonzo (September)
🚗
Next stop
Distance: 27 km
Travel time: 33min
13
Day

Radicofani

mountaintop fortress medieval drama

Radicofani - Photo 1Radicofani - Photo 2Radicofani - Photo 3Radicofani - Photo 4Radicofani - Photo 5Radicofani - Photo 6
6 photos
Day 13
🔍

Discover

1
Borough of Val d'Orcia
2
Borough at the foot of Monte Amiata
🎯

Activities

→
Exhibitions and cultural events
→
Surrounding nature
🚗
Next stop
Distance: 10 km
Travel time: 13min
14
Day

Piancastagnaio

chestnut village mountain refuge

Piancastagnaio - Photo 1Piancastagnaio - Photo 2Piancastagnaio - Photo 3Piancastagnaio - Photo 4Piancastagnaio - Photo 5Piancastagnaio - Photo 6Piancastagnaio - Photo 7Piancastagnaio - Photo 8Piancastagnaio - Photo 9Piancastagnaio - Photo 10
10 photos
Day 14
🔍

Discover

1
Rocca di Piancastagnaio (medieval fortress)
2
Therapeutic thermal springs (hot all year round)
🎯

Activities

→
Southern Val di Chiana landscape
→
View over the Val di Chiana
🚗
Next stop
Distance: 20 km
Travel time: 24min
15
Day

San Casciano Bagni

thermal village healing tradition

San Casciano Bagni - Photo 1San Casciano Bagni - Photo 2San Casciano Bagni - Photo 3San Casciano Bagni - Photo 4San Casciano Bagni - Photo 5San Casciano Bagni - Photo 6San Casciano Bagni - Photo 7San Casciano Bagni - Photo 8San Casciano Bagni - Photo 9San Casciano Bagni - Photo 10
10 photos
Day 15
🔍

Discover

1
Prehistoric archaeological site
2
Archaeological museum
🎯

Activities

→
Archaeological visit
🚗
Next stop
Distance: 13 km
Travel time: 16min
16
Day

Cetona

mountain village ancient gateway

Cetona - Photo 1Cetona - Photo 2Cetona - Photo 3Cetona - Photo 4Cetona - Photo 5Cetona - Photo 6
6 photos
Day 16
🔍

Discover

1
Preserved medieval buildings
2
Ancient castle surrounded by holm oaks
3
Etruscan necropolis
🎯

Activities

→
Renaissance historic center
🚗
Next stop
Distance: 9 km
Travel time: 11min
17
Day

Sarteano

valley village Etruscan wonder

Sarteano - Photo 1Sarteano - Photo 2Sarteano - Photo 3Sarteano - Photo 4Sarteano - Photo 5Sarteano - Photo 6
6 photos
Day 17
🔍

Discover

1
Etruscan remains
2
Village of the Val di Chiana Senese
3
Historic caves carved in rock
🎯

Activities

→
Archaeological visit
🚗
Next stop
Distance: 14 km
Travel time: 17min
18
Day

Montepulciano

wine city hill fortress

Montepulciano - Photo 1Montepulciano - Photo 2Montepulciano - Photo 3Montepulciano - Photo 4Montepulciano - Photo 5Montepulciano - Photo 6
6 photos
Day 18
🔍

Discover

1
Capital of Vino Nobile di Montepulciano
2
Historic caves carved in rock
3
Capital of Vino Nobile di Montepulciano
🎯

Activities

→
Renaissance historic center

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🛡️ Travel advice - Italy

Check official recommendations

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❓ Frequently asked questions

What weather should you expect?

Spring (April-June): Perfect weather, blooming landscapes, comfortable temperatures, fewer crowds, excellent value, Easter celebrations, ideal touring conditions.

Summer (July-August): Warmest weather, peak tourist season, highest prices, crowded attractions, vibrant atmosphere, beach season, festival time.

Fall (September-October): Excellent weather, harvest season, wine tourism, comfortable temperatures, fewer crowds, beautiful colors, culinary focus.

Winter (November-March): Mild southern weather, Christmas markets, lowest prices, minimal crowds, cultural focus, cozy atmosphere, indoor attractions.

How many days should I plan?

We believe you will enjoy this itinerary best by dedicating between 15 and 23 days. The next step will allow you to adjust the duration of your stay.

What to discover in Italy?

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