📍 Italy

SIENA PROVINCE COMPLETE: WINE, WALLS AND MEDIEVAL GRACE

Ramparts ringing medieval villages, Chianti slopes yielding purple wine, brick towers piercing sky. Timeless Tuscany.

≈ 11
Days
258
Km
10
Stops
📖 6 min read 🔄 Last updated: 2026-01-17

Let Siena and its warm brick guide you, then reach San Gimignano's towers. Cross Monteriggioni, follow Radda's vineyards, trace Asciano's lunar landscapes and relax at Rapolano's springs. Montepulciano, Pienza and Montalcino punctuate a journey of stone, wine and open horizons.

Your day-by-day itinerary

1
Day

Siena

brick heart medieval splendor

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

Discover

1
Piazza del Campo and Torre del Mangia
2
Duomo di Siena and its marble pavement
3
Museo dell'Opera Metropolitana
4
Santa Maria della Scala
+1 Places visited
🎯

Activities

→
Walk through the medieval historic center
🚗
Next stop
Distance: 37 km
Travel time: 44min
2
Day

San Gimignano

tower realm medieval skyline

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

Discover

1
Collegiata di Santa Maria Assunta and its frescoes
2
Museo Civico and Torre Grossa
3
Fortified walls of Monteriggioni
🎯

Activities

→
Panorama from the towers over the Tuscan countryside
🚗
Next stop
Distance: 22 km
Travel time: 26min
3
Day

Monteriggioni

wine tradition valley heart

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6 photos
Day 3
🔍

Discover

1
Museo Monteriggioni in Arme
2
Castellina in Chianti - fortress and archaeological museum
🎯

Activities

→
Walk on the medieval ramparts
🚗
Next stop
Distance: 21 km
Travel time: 25min
4
Day

Radda In Chianti

crete cliffs clay landscape

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 4
🔍

Discover

1
Radda in Chianti - Palazzo del Podestà
2
Gaiole in Chianti - Brolio Castle
3
Abbey of Monte Oliveto Maggiore and its frescoes
🎯

Activities

→
Discovery of the wine landscapes of Chianti Classico
🚗
Next stop
Distance: 42 km
Travel time: 50min
5
Day

Asciano

thermal springs healing waters

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

Discover

1
Asciano - Civic Archaeological and Sacred Art Museum
2
San Giovanni d'Asso - Truffle Museum
3
Museum of the Ancient Grancia and Oil
🎯

Activities

→
Crossing the lunar landscapes of the Crete Senesi
🚗
Next stop
Distance: 9 km
Travel time: 11min
6
Day

Rapolano Terme

wine fortress hill crown

Rapolano Terme - Photo 1Rapolano Terme - Photo 2Rapolano Terme - Photo 3Rapolano Terme - Photo 4
4 photos
Day 6
🔍

Discover

1
Piazza Grande and Palazzo Comunale
🎯

Activities

→
Relaxation at the thermal baths of Rapolano
🚗
Next stop
Distance: 33 km
Travel time: 40min
7
Day

Montepulciano

Renaissance palace village soul

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

Discover

1
Cathedral of Santa Maria Assunta
2
Temple of San Biagio
3
Renaissance Center of Pienza
🎯

Activities

→
Visit to the historic underground cellars
🚗
Next stop
Distance: 11 km
Travel time: 14min
8
Day

Pienza

noble wine hilltop jewel

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

Discover

1
Cathedral and Piccolomini Palace
2
Chapel of the Madonna di Vitaleta
3
Bagno Vignoni - historic thermal resort
4
Fortress of Montalcino
🎯

Activities

→
Panoramic views of Val d'Orcia
🚗
Next stop
Distance: 20 km
Travel time: 24min
9
Day

Montalcino

noble wine hilltop jewel

Montalcino - Photo 1Montalcino - Photo 2Montalcino - Photo 3Montalcino - Photo 4Montalcino - Photo 5Montalcino - Photo 6
6 photos
Day 9
🔍

Discover

1
Abbey of Sant'Antimo
2
Civic and Diocesan Museum
3
Duomo di San Cerbone
🎯

Activities

→
Discovery of the Brunello wine hills
🚗
Next stop
Distance: 63 km
Travel time: 1h16
10
Day

Massa Marittima

coastal town maritime heritage

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

Discover

1
Mining Museum
2
Parco delle Colline Metallifere
3
Parco delle Colline Metallifere
🎯

Activities

→
Visit to Etruscan and Roman mining heritage

🗺️ Itinerary map

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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 9 and 13 days. The next step will allow you to adjust the duration of your stay.

What to discover in Italy?

Cultural masterpiece with incredible art, cuisine, and historical heritage from Rome to Venice. Experience Renaissance treasures, regional diversity, and authentic Italian lifestyle. The country offers cultural immersion with culinary excellence and artistic heritage. Italy provides complete cultural experiences with historical significance and natural beauty.