Siena

Siena is the gateway to southern Tuscany's greatest wines. The medieval city — famous for the shell-shaped Piazza del Campo, its striped cathedral and the twice-yearly Palio horse race — sits at the crossroads of Chianti Classico to the north and the Brunello and Vino Nobile country of Montalcino, Montepulciano and the Val d'Orcia to the south, with San Gimignano's Vernaccia hills to the west.

That makes it an ideal base for tasting without long transfers: most of the region's marquee estates are within an hour's drive, and the old town has plenty of enotecas to taste across Tuscany before you head out. The compact historic center is walkable and largely car-free, so plan to leave the car outside the walls and use it for day trips into the hills.

Siena is about 75 minutes from Florence by road (the rail link is slower and less direct), and slots naturally into a Chianti-plus-Val-d'Orcia loop. Spring and early autumn are the sweet spots; the Palio fills the city on July 2 and August 16. Use the guide below to plan tastings and vineyard day trips from the city.