Florence, Siena & Chianti

Two great cities and the hills between

This is the Tuscany most people picture: the Renaissance city of Florence to the north, medieval Siena to the south, and between them the rolling hills of Chianti, with vineyards, olive groves, cypress-lined drives and stone farmhouses. Both city centres are UNESCO World Heritage Sites, and the countryside between them is small enough to explore from a single base.

Florence needs several days on its own, from the cathedral and Brunelleschi's dome to the Uffizi, the Ponte Vecchio and the Oltrarno's artisan workshops. Its churches, markets and gardens reward slow exploring, and the hills of Fiesole look down over the city. Siena is smaller and more intimate, centred on the shell-shaped Piazza del Campo, where the Palio horse race is held each summer, and its striped cathedral.

Chianti villages and nearby towns

The Chiantigiana road runs through the heart of the wine country, linking Greve in Chianti, with its arcaded market square, to Panzano, Castellina, Radda and Gaiole. Each is a good place for lunch and a wine tasting, and many estates welcome visitors. Look for the black rooster on bottles of Chianti Classico.

West of the Chianti hills, San Gimignano is famous for its medieval towers and is also UNESCO listed, while the walled village of Monteriggioni sits on a hilltop just north of Siena. The Val d'Orcia and Montepulciano are within reach for a longer day out.

Food, travel and when to visit

Tuscan food is generous and simple: bistecca alla fiorentina, ribollita, pecorino, cured meats and new-season olive oil in late autumn. Siena is known for panforte and ricciarelli biscuits.

Florence and Pisa are the nearest airports, and a car is almost essential once you are in the countryside. Spring and early summer are green and pleasant, July and August are hot, and September and October bring the grape harvest. The area suits families, groups of friends and couples who want culture, food and countryside together.

Explore more of Tuscany, or browse the villas listed below to find your base between Florence and Siena.