Of the many castles that rise up in the Radda territory, that of Volpaia is most worth a visit. Today as in the eleventh century, the whole town is involved in the production of wine and olive oil. The wine presses and wineries are now often found underground, in deconsecrated churches, or in purpose-built places inside the town, linked by an unexpected subterranean "vinoduct".
Outside Radda, you might visit the parish church of Santa Maria Novella which, despite heavy restructuring work over the years, has managed to preserve its original Romanesque plan, as well as its numerous artworks.
Indeed, the Radda area is littered with pieces of the Romanesque, of which the church of Santa Maria in Prato is a shining example. This church contains a fifteenth-century Madonna and Child by Neri di Bicci, while its adjoining monastery has the Casa del Chianti Classico (Chianti Classico House) with exhibition rooms, in-depth guides and a hands-on educational tour through the wine's history.
It's but a few minutes' journey from Radda in Chianti to other Chianti villages, such as Castelnuovo Berardenga and Gaiole in Chianti. Keen cyclists can take the Eroica, a permanent route that follows dirt roads from the Chianti into the Crete Senese and then the Val d'Orcia.