An experience from last year at the outdoor Swing Night at the Boston Harbor Hotel:
There's a band on the float in front of the outdoor stone gazebo every Wednesday. We got a table at Intrigue, the outdoor cafe, while people lined up to get tables along the water and cushions for the stairs.
The people watching at Rowes Wharf is by far the best in Boston. In my opinion, it is rivaled only by Au Bon Pain in Harvard Square. Fanueil Hall does not even deliver the entertainment of some of the oddities that appear here on the waterfront. Women with knee-length green hawaiian print skits and white knee socks, men with polyester 3 sizes too small tank tops, handsome men with girlish shoulder length cornrows....the free-spirited, the overly pretentious, the wealthy yet low-class....it's all here folks.
We sat and lounged over dinner with cocktails and then a few beers. Our waiter was unattentive, the food mediocre and very overpriced. But the sounds of Frank Sinatra wafted over to our little table, a warm and beautiful night, a cold beer, and sights abound. A wonderful way to spend a Wednesday.
So, for a nice evening out, go down to the hotel, get there early, grab a cushion, and listen to some blues or swing for free. Try to avoid the restaurant and just grab something to eat beforehand. They also show movies, so check it out.