Tuscany’s famous towns are famous for reasons that hold up: Siena is magnificent, San Gimignano’s towers are striking, Montepulciano earns its wine reputation. But all three are also genuinely overwhelmed by tourism in summer — tour buses, queues, menus in four languages. The Tuscany that most people are actually looking for exists 20 minutes down the road, in towns that appear on no bus tour itinerary and where the trattoria has one handwritten menu in Italian.
Monticchiello
South of Pienza, near the Val d’Orcia that appears in every Tuscan landscape photograph, sits Monticchiello — a medieval walled village of about 200 permanent residents with one restaurant, one bar, and views across cypress-lined valleys that rival anything in the region. It’s reachable by car only, has almost no accommodation (meaning day visitors clear out by 5pm), and the light on the stone walls at golden hour is extraordinary.
The Teatro Povero di Monticchiello puts on an outdoor theatrical performance each summer that the village has been running for over 50 years — entirely self-produced, performed by residents, and genuinely worth planning around if you’re in the area in July.
Val d’Orcia base: Stay in Pienza or Bagno Vignoni (a village with a thermal pool as its central piazza) and use those as bases for exploring this corner of Tuscany. Both are beautiful and underrated compared to Siena and San Gimignano.
Pitigliano: The Little Jerusalem
Pitigliano in the Maremma (southern Tuscany, largely ignored by international tourism) sits on a volcanic tuff cliff that the town appears to grow from. The historic Jewish quarter — called “Little Jerusalem” for the large Sephardic community that lived here from the 16th century — is unusually intact. The wine produced in the surrounding area (Pitigliano DOC, made from Trebbiano and Greco grapes) is excellent and little-known outside the region.
Sovana
Near Pitigliano, Sovana is a medieval village of extraordinary architectural density for its size — a Romanesque cathedral, Etruscan tombs in the surrounding Via Cava (sunken road), and a historic center that takes about 20 minutes to walk end to end. The Etruscan necropolis accessible from the village is one of the better-preserved in Tuscany. Almost no one comes here.
Cetona
On the Umbrian border, Cetona has a perfectly preserved medieval piazza, a good local restaurant scene (fueled in part by the Fonteverde spa resort nearby), and the kind of atmosphere where a resident will invite you in for a glass of wine if you stop to admire their garden. The weekly market is legitimate — locals shopping, not tourists buying ceramics.
Driving Southern Tuscany
- Car essential: These villages have minimal or no bus connections; rent from Florence, Siena, or Rome
- SP roads: Strada Provinciale roads through the Val d’Orcia are some of the most beautiful drives in Europe — go slow and stop often
- Lunch hours: Restaurants in these villages are serious about lunch (12:30–2:30pm) and dinner (7:30–10pm); don’t arrive at 3pm expecting a meal
- Best season: April–June and September–October for the most beautiful light; avoid August when even the quiet villages fill up
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