I have found there's no better way to get to know a new city than to take a tour of its downtown entertainment or bar district, which is why I generally like to go on a "pub crawl" one night when I travel.

Start in a local pub or bar, have a drink or two, and move onto the next one. I find it more enjoyable to find the truly local establishments, and not the national franchises. It makes for a fun night and great stories.

Pro tip: consider wrapping a "progressive dinner" into your pub crawl for more diversity... and less chance of a hangover.