Tuscany in late autumn and early winter has a magic all of its own. The summer crowds have drifted away, the hills are painted in burnt orange and gold, and the pace slows to something far more local. This is the season for hearty dishes, truffle hunting, long lunches, and the joy of wandering through medieval streets where the scent of roasting chestnuts lingers in the air.
November
Fiera Antiquaria – Arezzo
First weekend of November
Only 45 minutes from Cortona, the famous antique fair in Arezzo’s Piazza Grande is a treasure trove of vintage furniture, paintings, ceramics, and rare finds. More than 500 stalls fill the cobbled streets, making it the perfect excuse for a day trip with a long, lazy lunch in one of the town’s trattorias.
Festa di San Martino e dei Bringoli – Anghiari
Second weekend of November
This medieval hilltop town throws a weekend celebration in honour of San Martino. Bringoli – a thick handmade spaghetti – is served with rich local sauces, accompanied by grilled sausages, roasted chestnuts, and plenty of Tuscan wine, yum!
White Truffle Festivals
Throughout November in San Miniato & San Giovanni d’Asso
The earthy, intoxicating scent of white truffles fills the air at these traditional markets. Wander from stall to stall sampling cheese, honey, salumi, and wine – all laced with the flavour of this prized tuber.
Chestnut Festival – Castel San Niccolò
Second Sunday of November
This is a cosy mountain-town celebration of autumn’s favourite nut, with roasting fires, music, and home-baked cakes. Who doesn’t love the smell of roasting chestnuts? Why not buy some and bring them back to Palazzo Passerini and roast them on the fire?