Lounge Leo is tucked away on the outskirts of Little Italy, but it's a real treasure. Super tall drinks on tap for cheap, seating at three distinct areas, and the most interesting characters always show up.
The great part about it is that traffic is low during the weekdays, so I always come by, grab a cider, and read a book. When the weekend rolls around, more people show up, so it's always a good time if I decide to stop by.
Don't sleep on this place. It's great.