Chianti

Chianti is the rolling heart of Tuscany — the classic postcard of vineyards, olive groves, cypress avenues and stone hill-towns spread between Florence and Siena. At its center is Chianti Classico, the historic zone marked by the Gallo Nero (Black Rooster) seal, where Sangiovese makes structured, savory, food-friendly reds that are among Italy's most recognizable wines.

The wine road threads through a string of small towns, each an easy base or day stop: Greve, with its funnel-shaped market square; Panzano, known for its butcher and its hillside vineyards; and Castellina, Radda and Gaiole, the quiet stone villages higher in the hills. Estates range from centuries-old family castles to small organic growers, and most also press olive oil — a tasting here often means wine, oil and a long lunch on a terrace over the valley.

Chianti is best reached from Florence or Siena, both under an hour away, but a car is what unlocks it — the pleasure is the drive between cellars on the winding SR222 "Chiantigiana." Spring and early autumn are the sweet spots, with the vine-and-olive harvest energy peaking in September and October. Use the guide below to plan which wineries and tours to book and where to base yourself in the hills.