Montalcino has a 14th century Rocca or Fortress. You approach the town through olive groves and vineyards. From the fortress you look out over the whole province. Besides the fortress, there’s a neo-classical cathedral, a Romanesque church and a maze of intriguing alleys to explore.
From just outside Montalcino there is a wonderful walk down through woods and fields to the 12th Century abbey of San Antimo (about an hour and a half, perhaps longer if you take as many photos as there are opportunities!)