When you are in Roxbury to visit the Sam Adams Brewery, have lunch at Doyle's. It's down the street in Jamaica Plain. Twenty-one beers on tap. When Jim Koch introduces a new beer to the market, generally it gets poured at Doyle's first.
for being local to boston, with many freinds that currently live there or have lived there giving me unlimited places to stay and options to visit, ive only been a handful of times. the city doesnt do it for me and everthing shuts down at 2. but, im not much of a sports fan so that could be a potential reason as well. i do however go to NYC as often as i can.
Yes, skip the freedom trail and duck tours. Take in the city on your own.
If you are able/willing to travel around I would say hit up NH a little bit, maybe Portsmouth for a day trip (think it's about an hour away) or White mountains if you're up for a little bit of a drive.
Same thing you'd do in Boston - Eat, drink, walk around and check out breweries, haha. It's just a nice little New England city and was suggesting it in case you're like me and as much as you enjoy visiting the big cities its fun to get away and check out the smaller ones if you have time.