942 Penn Ave., Downtown
412-281-2810 or www.siennapgh.com/mercato
With a retractable glass roof, spacious bar and funky lighting, the perch atop this three-storied restaurant complex is a year-round destination for rooftop drinking. The people-watching views of the Cultural District and the action on Penn Ave below are unrivaled.
2nd: Hotel Monaco
3rd: Six Penn Kitchen