I went out to Pittsburgh when the Sox played there in 2010. A few suggestions:
- Highly recommend taking the PNC ballpark tour. I've done a few ballpark tours and the PNC one was by far, my favorite.
- There is an area of bars/restaurants/nightlife called the "South Side" Plenty of options for your crew. My personal favorite was "Fatheads" http://www.fatheadspittsburgh.com/
A lengthly list of beers on tap and some of the best wings I've ever had.
- The original Primanti Brothers is not too far from PNC, in the Strip District. Some people like their sandwiches, others say it's an overrated tourist trap.