San Casciano in Val di Pesa

San Casciano is the first Chianti town you reach from Florence, set on the ridge between the Pesa and Greve valleys. It keeps imposing stretches of its medieval walls and towers, and a small historic centre that feels more lived-in than visited. Less than half an hour’s drive from Florence, it makes a sensible first or last night on a trip that begins or ends in the city.

In the Chiesa della Misericordia, also called Santa Maria al Prato, hangs a painted crucifix by Simone Martini, a masterpiece of Sienese painting this far north. The Museo Giuliano Ghelli, in the church of Santa Maria del Gesù, gathers sacred art from the surrounding parishes, including works by Coppo di Marcovaldo and Ambrogio Lorenzetti, together with Etruscan finds from the area.

Just outside the town, at Sant’Andrea in Percussina, stands the Albergaccio, the house where Niccolò Machiavelli lived in exile after 1513 and wrote The Prince. At Bargino, the Antinori family’s winery is cut into the hillside, its roof planted with vines — one of the most striking pieces of contemporary architecture in Tuscany.

Only part of the comune lies within Chianti Classico. The San Casciano UGA is broad and gentle, about 1,560 hectares of vines between roughly 150 and 375 metres, and its wines are round and fruit-led, a little more austere on the alberese in the south. Mercatale and Montefiridolfi, to the south-east, are quiet villages in the heart of it.