First, purchase a biscotti from Enrico's Biscotti Co. I recommend the Chocolate Almond, but try not to eat it right away.
Then, run over to La Prima Espresso Co. and order a cappuccino.
Next, grab a seat next to the table of elderly Italian gentlemen (I hear they're there everyday), and watch them play cards as you sip & nom. -- This is the perfect way to start your Strip District feast.
After, walk next door to the Pittsburgh Popcorn Co. (Are you seeing a trend yet?)