Poised between tradition and modernity, rurality and industry, Castelfiorentino has always been a middle ground, at the crossroads between the Via Volterrana and the Via Francigena, on the border between Florence and Siena.

Castelfiorentino has ridden, more than other neighbouring towns, the wave of industrial modernity that since the 19th century, by train and on four wheels, has transformed not only its urban layout but also its social fabric.

In the Florentine orbit since 1149, Castelfiorentino has never betrayed the city of the lily, but has often changed skin, in step with the developments or implosions of its economy: this is why the Middle Ages dialogue with the Baroque 18th century and the bourgeois 19th century. From Piazza Gramsci, site of the Saturday market and the Teatro del Popolo – one of the most important 19th-century theatres in Tuscany – we walk through the streets of the centre to Via Testaferrata, a stone’s throw from the station, where the Benozzo Gozzoli Museum houses the frescoes and sinopites that the Florentine master painted for two local tabernacles between 1484 and 1490.

‘His painting, at once cultured and popular, is able to fascinate and explain with grace and wisdom.

Another unmissable stop for art lovers is the Baroque church of Santa Verdiana – the patron saint of Castelfiorentino – and the adjacent Museum of Sacred Art, which houses illuminated manuscripts, works by Annibale Gatti, Taddeo Gaddi, and a Madonna and Child attributed to Cimabue.

A few metres from Santa Verdiana, the Church of San Francesco is a rare example of Gothic architecture, a 13th-century complex whose origin is linked to the presence of the saint from Assisi in Valdelsa in 1217.

Returning towards the centre, the steep slope of Via Ferrucci crosses the only gate remaining from the ancient walls and follows on to Piazza del Popolo, in Castello Alto, the oldest part of Castelfiorentino. Here, the Palazzo del Comune, with its famous bell tower by Membrino, contrasts with the Collegiata dei Santi Lorenzo e Leonardo, a 13th-14th century church that houses works by Annibale Gatti and numerous relics. Continuing uphill, one arrives at the Pieve dei Santi Ippolito e Biagio, built at the end of the 1100s on the hill that dominates the entire town.

On Saturday mornings, during the weekly market – the goods market in Piazza Gramsci and the fruit and vegetable market in Piazza Kennedy – we recommend a stroll around the shops in the streets of the centre.