Wine & Cheese
Even though it's far tinier than neighboring hill towns, Pienza has about the same number of wine shops. The main difference is that these stores aren't tied to a single estate or producer (in Montalcino and Montepulciano, most enoteche are thinly disguised branches of nearby vineyards). Here you can often get a more well-rounded tasting experience, plus less biased advice.
These shops -- indeed, any food store in town -- usually double as outlets for other regional specialties, including the king of all sheep cheeses, Pienza's own pecorino (or cacio). You can get it fresco (fresh), semistagionato (partially aged), or stagionato (aged and suitable for grating, though it really needs a few extra years for that). Many pecorini are also dusted with ground materials to keep them soft and alter the taste slightly. Most popular are cenerato or sotto cenere (an ash coating that's mainly a softening technique), peperocinato (hot peppers), and tartufato (truffles). A few producers even mix ingredients directly into the cheese (tartufi are a favorite), but others claim this mars the purity of the pecorino. Luckily, you can judge for yourself, as pecorino tasting is even more popular here than wine tasting. Two of the best places are La Bottega del Cacio, Corso Rossellino 66 (tel. 0578-748-713), and the tiny La Bottega del Naturista, Corso Rossellino 16 (tel. 0578-748-760).
On Corso Rossellino you'll find several ceramics stores and the showroom for Biagiotti Fratelli (tel. 0578-748-666), a family of artisans who specialize in ferro battuto (cast iron). Its workshop and foundry is on SS146 on the way to Montepulciano. Calzoleria Pientina, down a side street at Via Gozzante 22 (tel. 0578-749-040 or 0578-748-195), handcrafts leather shoes to measure as well as bags and purses.