Gritty and hip, the busy seaport of Bari sits at the top of the heel of Italy’s boot. In the maze-like old town, practically every cobblestone street leads to a church. After you've had your fill of the architecture, wander into one of the many trattorias for the local cuisine paired with glasses of the area's full-bodied Primitivos. Bari is also the gateway to excursions in the olive grove- and vineyard-studded Puglia region.