A perfectly preserved medieval city of brick piazzas, Gothic palaces, and rolling Tuscan hills that feels like stepping into another century.
Siena moves at a different pace than Florence. The city is built across three hills, its streets narrow and steep, opening suddenly onto the vast, shell-shaped Piazza del Campo. The Duomo is a Gothic masterpiece, and the surrounding countryside of vineyards and cypress trees begins almost at the city walls.
It's a place for slow mornings, long lunches, and getting a little lost. The contrade — the city's historic neighborhoods — still shape local identity, and the Palio horse race in summer turns the piazza into one of Italy's most dramatic spectacles.
We love Siena as a base for exploring Tuscany without the crowds. Chianti, Montalcino, Pienza, and San Gimignano are all within easy reach, and the city itself rewards travelers who want atmosphere over checklists.
Trip highlights
- The shell-shaped Piazza del Campo and Torre del Mangia
- The striped marble Siena Duomo and Piccolomini Library
- Day trips through Chianti and the Val d'Orcia
- The Palio and the city's living contrada traditions
- Tuscan wine, pecorino, and long, leisurely meals
Where to stay
Hotel Certosa di Maggiano — Just outside Siena's city wallsA former 14th-century monastery turned intimate hotel, with vaulted ceilings, a quiet cloister garden, and views over the Tuscan countryside — only a short walk from the center.
Castello di Casole, A Belmond Hotel — Tuscan countryside, near SienaA restored 10th-century castle and estate surrounded by vineyards and olive groves. Spacious suites, a world-class spa, and an infinity pool with sweeping views of the Val d'Elsa.