Palio di Siena (of the Assumption)
📍 SienaThe world's most famous horse race: three laps of Piazza del Campo.
There is a reason half of Western painting was born here. Renaissance Tuscany — Florence, Siena, Pisa — fixed the very idea of Italian beauty for good. Yet the region lives well beyond its museums: in the clay hills of the Sienese crete and the UNESCO-listed Val d'Orcia, in the vine rows of Chianti and Montalcino, in the tower-village of San Gimignano and pope Pius II's "ideal city" of Pienza.
May and October are the right months. And in the evening, when the coaches leave, even Piazza del Campo belongs to the Sienese again — that's when Tuscany really shows itself.
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The places worth the trip on their own, picked by our editors.
Florence 🏛
Florence
The cradle of the Renaissance
Siena 🏛
Siena
Gothic beauty and the Palio
Montecatini-Terme ♨
Pistoia
UNESCO-listed Art Nouveau elegance
Greve in Chianti 🍷
Florence
The gateway to Chianti Classico
San Gimignano 🏘
Siena
The UNESCO-listed medieval towers
Manciano ♨
Grosseto
The free thermal falls of Saturnia
Chianciano Terme ♨
Siena
Etruscan waters between two Tuscan valleys
Montalcino 🍷
Siena
The kingdom of Brunello wine
Our editors' ranking: the area's most important places, drawn from the individual town guides. See the national rankings →
1
⛪ Churches & sanctuaries Cattedrale di Santa Maria del Fiore
📍 Florence
Completed in 1436, the colossal Florentine cathedral holds the absolute record for the world's largest masonry dome.
2
🖼️ Museums Galleria degli Uffizi
📍 Florence
Italy's most visited art museum houses the world's greatest collection of Renaissance masterpieces in a 1560 palace.
3
🏛️ Squares & old towns Piazza dei Miracoli e Torre Pendente
📍 Pisa
A 57-meter-tall 12th-century campanile, globally recognized for its 3.97-degree lean caused by ground subsidence.
The world's most famous horse race: three laps of Piazza del Campo.