Standing high atop a hill in southern Tuscany is the quintessential medieval Italian village of Montepulciano. The city, full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners, boasts vast panoramas all over the beautiful Val d’Orcia and Val de Chiano valleys that surrounds it. Although rather touristy with coachloads flocking in by the hour, you should not let that deter you from a stop here. I think the wine was some of the best we had our entire trip and the only place we actually bought a few bottles to bring home. Plan to wear comfortable shoes, the entire village is very hilly and after all the complimentary wine tastings, you’ll want to be surefooted. Also plan on bringing plenty of cash as there is some really great souvenir shopping.