Tuscany doesn’t end at Florence. Most of what makes Tuscany Tuscany happens in towns of 800 people on hilltops, where everyone eats lunch from 1pm to 3pm and nobody works.
I lived in Chianti for a year. Here are the ten places I’d send my best friend.
1. Volterra
An hour west of Siena. Etruscan walls older than Rome. The alabaster workshops are real – they’ve been carving the same translucent stone for 2,800 years. Climb the medieval fortress at sunset. Eat at La Vena di Vino, drink the local Sangiovese, walk home through silent stone streets.
2. Pitigliano
The “Little Jerusalem” of Tuscany – tucked into a cliff face, a synagogue from the 1500s, a Jewish cemetery on the rocks below. The wine is white (Bianco di Pitigliano) and underrated. Stay in a cave hotel cut into the tuff stone.
3. Montepulciano
Yes it’s on tour bus routes but they leave at 5pm. After that, the Renaissance town empties out and you can eat at La Grotta di San Biagio in peace. The Vino Nobile here is some of the most underrated red wine in Italy.
4. Castagneto Carducci
The Tuscan Maremma coast – flatter, hotter, less famous than Chianti. This village is where the cyclists come on weekends. Bolgheri Sassicaia (one of the most expensive wines in Italy) is made down the road. Drive the Cypress Avenue at dawn.
5. Lucignano
The most beautifully laid-out medieval town in Italy. Four perfect concentric rings of buildings around a central tower. Walk in circles intentionally. Eat at Il Goccino. Population: 800. Tour bus probability: low.
6. Massa Marittima
Real medieval cathedral, real working town, real food. Almost no tourists because nobody knows it. Walk the walls, eat wild boar pappardelle, sleep with the window open and hear nothing but church bells.
7. Anghiari
Where Leonardo da Vinci painted the lost Battle of Anghiari mural. Steep streets, knife-makers (the town’s been famous for blades for 800 years), Sunday market that hasn’t changed since 1300.
8. San Casciano dei Bagni
The Romans had hot springs here. Most are free, the fancy hotel has eight pools and a stone bath cut into the hillside. The town itself is tiny, gorgeous, and full of old men playing cards in the bar at 11am.
9. Cortona
OK it’s in “Under the Tuscan Sun” so there’s some tourism. But the early-morning hours are still magic. Climb to the top, watch the mist over Lake Trasimeno, then go down for breakfast at Caffe Tuscher. The Etruscan museum is small and astonishing.
10. Civita di Bagnoregio
Technically Lazio, but I’m including it because you need to see it. A 5-foot-wide footbridge is the only access. The town is literally crumbling into the valley below. Population at this point: about 11. Go before it falls.
How to do this properly
Rent a car in Florence or Pisa. Drive through these towns over 7-10 days. Stay 2 nights minimum in each spot. The villages reveal themselves slowly – you can’t day-trip Tuscany.
October is the move. Crowds gone, harvest happening, food best, prices halved. Skip Florence entirely if you can – it’s not what Tuscany is.