Southern Tuscany, Italy - Travel Guide
By MupDay - the planner that does the research for you.
Updated: 2026-08-14
Southern Tuscany offers picturesque landscapes of rolling hills, endless vineyards, and medieval towns. It's a perfect destination for wine lovers, foodies, history buffs, and nature enthusiasts, combining rural tranquility with cultural richness.
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Top things to do in Southern Tuscany
The must-see places in Southern Tuscany include Val d'Orcia, Piazza del Campo, San Gimignano, Duomo di Siena, Chianti Classico Wine Region and more. Here is the full list, with a short note on each:
- Val d'Orcia · Pienza
A picturesque valley, a UNESCO World Heritage site, with iconic landscapes of rolling hills and cypress trees.
- Piazza del Campo · Siena
Siena's famous central square, one of Italy's most beautiful, featuring stunning architecture and the Torre del Mangia.
- San Gimignano · Val d'Elsa
A walled medieval town with 14 ancient towers, offering spectacular panoramic views.
- Duomo di Siena · Siena
A magnificent Gothic cathedral with a lavish facade, stunning mosaics, and important artworks inside.
- Chianti Classico Wine Region · Greve in Chianti
A world-renowned wine region with numerous wineries, endless vineyards, and charming towns.
- Pienza · Val d'Orcia
A perfect Renaissance town known for its Pecorino cheese and meticulously planned architecture.
- Montepulciano · Val di Chiana
A beautiful hilltop town famous for its excellent wines and breathtaking views.
- Terme di Saturnia · Saturnia
Famous natural hot springs with tiered pools, offering a relaxing and therapeutic bathing experience.
- Cortona · Val di Chiana
An ancient Etruscan hilltop town with magnificent panoramic views of the Chiana Valley.
- Castelgiocondo
- Sito Archeologico della Pieve di San Pietro a Pava
- Castello di Bibbiano
- Castello Romitorio
- Montalcino · Val d'Orcia
A historic wine town with an impressive fortress, famous for its Brunello di Montalcino wine.
- Museo del Tartufo e Centro di Documentazione
Frequently asked questions
What are the must-see places in Southern Tuscany?
Val d'Orcia, Piazza del Campo, San Gimignano, Duomo di Siena, Chianti Classico Wine Region, Pienza
When is the best time to visit Southern Tuscany?
Any season works - MupDay plans around opening hours and the weather, and rebuilds your days as you add or remove places.
How do I plan an itinerary for Southern Tuscany?
Pick places in MupDay and it auto-builds a day-by-day route with no zig-zag, weather-aware.
