I knew I shouldnt have opened this thread! Damn I miss that city! The most underated northeast city imo. Some stuff came up or I'd be there with ya.
Everyone loves the advice given by locals but for me it was bittersweet &a walk down memory lane. I went to school there, I lived downtown for a year and on southside for a few.
There is a casino now? Wow, I left just before all the money got in place. The convention center was going in and stadiums on there way. All the extra development from southside works to waterfront were long planned projects that actually got done. Great to see for that struggling city too rise back up.
If you are young and without kids, I'd take all his advice very seriously. I'll add a few nuggets:
I know everyone knows about Primanti Brothers sandwiches, the best there is, btw! Also go to the deli on southside (16th/Carson I'm not sure cause it moved a block or two) and try anything. I sold more Steamed Reubens, Godfather's & Italian sandwiches than anything, ;-)
For fine dining and if with your woman take the drive or trolley up mount Washington at night and go to one of the restaurants on the cliffside. Great places but the names elude me right now. From this vantage point, the city is really stunning at night. Eating dinner with floor to ceiling windows on the edge of the mountain and the white glove service u can expect up there will leave your women's inhibitions behind.
I'm guessing Bettis's place is the old woodsons (next to station square), that would be a good place for brunch &beers, then u can hit station squares places for more scenery. From there hop a cab down Carson street to 17th street for the deli.
BTW there is a Primanti Brothers is across from Fat heads (19th & Carson) this place has more Beer Taps than tables but it has a great selection and as stated before great food too. If its still there, Shootz cafe is a great billiard hall down by 23rd and Carson. That would be a great afternoon and early evening. I'm not sure about nightlife, its so trendy and places change names every 2 years. He said there is a Buckhead Saloon in station square, awesome. Funny, Buckhead Saloon in Atlanta GA were basically my neighbors years ago and if its anything like the original, you must go there!