Schooner Wharf is one of my favorite places
I think moms and boys would both enjoy lunch there for michael mccloud who plays 12-5 Wed-Monday. (so not on Tuesday). Outside seating, over sand, right along the water with good music. Can't be beat on a good sunny day.
The food is decent (never had a bad meal, but burgers-wraps-fish-bar food type stuff ... nothing too special) and it IS a bar (so if you are teetotalers, I'd say to avoid it; but, otherwise there are rarely inappropriate drunks there ... just people enjoying a cold drink in the sun). but it IS totally key west and an afternoon there is a must do every time we go (a couple of times a year).
Blue Heaven is cool with the chickens running around. We like Willie T's.