Siena
Best for: First-timers, walkers, Palio fans
Italy's most beautiful medieval city — the shell-shaped Piazza del Campo, the Duomo, and narrow streets. A perfect base for day trips to Chianti, San Gimignano, and the Crete Senesi. Stay inside the walls.
Val d'Orcia (Pienza/Montalcino/Montepulciano)
Best for: Wine lovers, photographers, romantics
The cypress-lined roads from every Tuscany photo. Brunello wine in Montalcino, pecorino cheese in Pienza, Vino Nobile in Montepulciano. UNESCO-listed landscape. Car essential.
Chianti
Best for: Wine lovers, cooking classes
Between Florence and Siena — vineyards, olive groves, stone farmhouses. Greve in Chianti is the main town. The Chiantigiana road (SR222) is Italy's best wine route. Agriturismo heaven.
Lucca
Best for: Cyclists, families, quieter pace
A perfectly preserved walled city you can cycle around on top of the walls. Less touristy than Siena or San Gimignano. Excellent food. Easy train to Pisa (30 min) and Florence (1.5 hrs).
An Agriturismo
Best for: Couples, families, food lovers
A working farm offering accommodation, meals from the property, and total tranquillity. The Tuscan agriturismo experience — pool, wine, olive oil, sunset — is unmissable. Car required.
Our recommendation
Siena for the best hilltop town, Val d'Orcia for the most beautiful landscape, an agriturismo anywhere for the most authentic experience. Rent a car from Florence for the countryside portion.