Val d'Orcia Cycling & the Cypress Avenues
The Val d'Orcia, the UNESCO-listed valley that unfolds directly south and west of Montepulciano, contains some of the most photographed rural scenery on earth — rolling clay hills, lone farmhouses, and the famous cypress-lined white gravel roads known as strade bianche. Exploring it by bicycle from Montepulciano is one of the great slow-travel experiences of Tuscany.
The Classic Cypress Road
The most iconic cypress avenue in the area runs up to the Agriturismo Poggio Covili near Castiglione d'Orcia, about 30 km from Montepulciano, but there are equally beautiful examples much closer: the road leading to Agriturismo La Foce near Chianciano Terme has a long cypress-lined avenue that is especially magical at dawn when mist fills the valley below.
The La Foce estate gardens, designed by Cecil Pinsent in the 1930s, are open to the public on Wednesday afternoons and weekend mornings — a serene formal Italian garden perched above the wild clay landscape of the crete senesi.
Cycling Routes from Town
Rent an e-bike from Montepulciano Bike (Via Gracciano nel Corso) and follow the gravel track south from Porta di Grassi through the Cervognano vineyards to the hamlet of Montefollonico — a round trip of about 22 km with minimal traffic and constant vineyard views.
The route passes through the heart of the Vino Nobile production zone, and in late September you will cycle alongside active harvest teams picking Sangiovese by hand. Stop at any agriturismo along the way — most will sell you a glass of wine and a plate of bread and oil without ceremony.
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