Catsellina is essentially one street (for tourists), so once you've done it a couple of times, why not follow this parallel passage. Not much in it but the medieval architecture is both original and superb.

This largely covered pedestrian pathway forms a semi-circular route that joins the main street, Via Ferrucchio, at either end of that street's pedestrian only section. The pathway is relatively flat, only rising slightly at each end, and is approximately 200-300 metres long. The pathway was originally uncovered and ran alongside the eastern side of the city walls. I understand that as security concerns regarding invasions of the city subsided people began to build new, and expand existing, buildings out to meet the city walls thereby covering over the pathway and creating a series of tunnels. Several of the buildings that front the main Via Ferruccio also back onto the Via delle Volte including a very good Enoteca that also sells olive wood products. On the other side of the pathway are openings, some covered with glass, that offer some very good views down the hill over the vineyards. There are several other shops, wine cellars and galleries along the tunnel route and we particularly like the photography shop which has a great display of photos of the Tuscan landscape. When we have people stay with us we always take them to Castellina in Chianti as it is so pretty and show them the Via delle Volte as it is so unusual