12 Best Tuscan Villages Near Siena (2026)

Siena is the best base in central Tuscany for visiting medieval villages: Chianti is north, Val d'Orcia is south, San Gimignano is west. Most of the famous ones are under an hour by car.

You'll need a rental car. Public buses connect a few villages from Siena's Piazza Gramsci but schedules are unreliable and one-way only. Pick up a car at Siena station or Florence airport, drive slow.

1. Monteriggioni — 20 minutes north

The perfect walled village. 14 towers, a tiny circular piazza, two trattorias, a wine bar. 1-hour visit, perfect 30-minute stop on the way north. Free to enter the village; €5 to walk the walls.

• Eat: ribollita and crostini at any of the central trattorias, €20-30.

2. San Gimignano — 50 minutes northwest

The most famous Tuscan village — the medieval skyline of 14 surviving towers (out of 72 originally). Famous for Vernaccia white wine and saffron. Brutal crowds 11 AM - 3 PM in season; go before 10 AM or after 4 PM.

• See: Piazza della Cisterna, climb Torre Grossa (€9), Collegiata church (€5 with frescoes)
• Eat: gelato at the famous Sergio Dondoli stand on Piazza della Cisterna (yes, it lives up to the hype)
• Time needed: half day

3. Volterra — 1h15 west

Older than San Gimignano (Etruscan origins, 7th century BC), famous for alabaster workshops. Quieter, more atmospheric, fewer tour buses.

• See: Roman theatre, Etruscan museum, alabaster workshops on Via Porta all'Arco
• Eat: wild boar pappardelle in a stone trattoria, €25-35
• Time: half day

4. Colle di Val d'Elsa — 35 minutes northwest

Underrated. Famous for crystal glass production (60% of Italian crystal comes from here). The upper town (Colle Alta) is medieval, almost empty of tourists.

• See: Crystal Museum (€5), Colle Alta walking loop
• Time: half day

5. Pienza — 1h south (Val d'Orcia)

The Renaissance pope village. Designed in the 1460s as the "ideal city" by Pope Pius II. Tiny, perfectly proportioned central piazza. Pecorino di Pienza (sheep cheese) is the local specialty.

• See: Piazza Pio II, the cathedral, the loggia behind the town hall with views over Val d'Orcia
• Eat: a tagliere of pecorino with chestnut honey, €12-18
• Time: 2-3 hours

6. Montepulciano — 1h15 southeast

Steep, dramatic, full of wine cellars carved into the tufo rock. Famous for Vino Nobile di Montepulciano DOCG.

• See: Piazza Grande, Tempio di San Biagio (Renaissance church just outside the walls), one wine cellar (most offer free tastings of 2-3 wines)
• Eat: pici with duck ragù, €18-25
• Time: half day (longer with wine tasting)

7. Montalcino — 1h10 south

Brunello di Montalcino — one of Italy's most important wines. The village itself is small but the fortress dominates the hilltop.

• See: the fortress (free + €4 for ramparts), one or two wineries in the countryside (book ahead — try Castelgiocondo, Casanova di Neri, or smaller ones recommended by your hotel)
• Eat: pinci (the local spelling of pici) all'aglione, €20-28
• Time: half day for the village, full day if you add winery visits

8. Sant'Antimo Abbey — 1h20 south

10 km south of Montalcino, a 12th-century Romanesque abbey in a deep valley of olive groves. Free entry. Gregorian chant occasionally during services. Pair with Montalcino on the same day.

• Time: 1 hour

9. Buonconvento — 30 minutes south

A walled village on the old Via Cassia. Skipped by tour buses — too small. Locals come here for one of the best ribollita in the region.

• See: walk the walls, the small museum of sacred art
• Eat: traditional Tuscan trattoria, ribollita + tagliatelle al cinghiale, €25-30
• Time: 1-2 hours

10. San Quirico d'Orcia — 45 minutes south

The gateway to Val d'Orcia — the postcard landscape (rolling hills, cypress lanes, isolated farmhouses) that's on every Tuscany screensaver. The village itself is small but has the wonderful Horti Leonini Renaissance gardens.

• Photo stop nearby: the Cappella della Madonna di Vitaleta (5 minutes' drive), and the Cipressi di San Quirico
• Time: 2-3 hours

11. Asciano + Crete Senesi — 30 minutes east

Asciano is a small medieval town; the real reason to go is the Crete Senesi landscape that surrounds it — bare clay hills, white roads, isolated cypresses. The Monastery of Monte Oliveto Maggiore (10 minutes from Asciano) is a 14th-century Benedictine abbey with extraordinary cloister frescoes.

• Time: half day, ideally at golden hour
• Photo: the road from Asciano to Buonconvento (SP451), one of the most photographed in Tuscany

12. Castelnuovo Berardenga — 25 minutes east

Chianti Classico without the crowds. A small village with a medieval centre and a handful of excellent wineries nearby (Felsina, Fattoria di Castelnuovo).

• Eat: a Chianti restaurant with vineyard view, €35-50
• Time: half day with one winery

Suggested loops

1-day loop (northwest) **Siena → Monteriggioni → San Gimignano → Volterra → back via Colle di Val d'Elsa**. Total driving ~3h, with stops a full day.

2-day loop (south, Val d'Orcia) **Day 1**: Siena → Pienza → Montepulciano (sleep there). **Day 2**: Montepulciano → Montalcino → Sant'Antimo → back to Siena.

1-day loop (Crete Senesi) **Siena → Asciano → Monte Oliveto Maggiore → Buonconvento → back via SP451**. Slow drive, photo-heavy.

Practical driving notes

• ZTL: every historic village centre is restricted. Park in the marked lots outside the walls.
• Petrol: cheaper at supermarket pumps (Esselunga, Coop) than at autostrada stations.
• Country roads: narrow, winding. Drive slowly, especially after rain.
• Lunch: many village trattorias close 3-7 PM. Eat between 12:30 and 2:30 PM or you'll go hungry.

Where to eat in each village (quick picks)

• Monteriggioni: il Pozzo
• San Gimignano: Dorandò, Cum Quibus
• Pienza: La Bandita Townhouse Caffè, Trattoria Latte di Luna
• Montalcino: Re di Macchia, Boccon Divino
• Montepulciano: Osteria dell'Acquacheta, Le Logge del Vignola
• Buonconvento: I Poggi
• Volterra: Ristorante Enoteca del Duca

Keep reading

• Siena vs San Gimignano: which is worth your time?
• Siena, Italy: the complete 2026 travel guide
• Where to stay in Siena: best areas + honest picks
• Where to eat in Siena: a local foodie's guide

*Planning a Tuscan villages itinerary and want suggestions? Email us at redazione@visitsienaguide.it.*