PP2
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I would take a Duck Boat tour. I've done a few and they are always fun and a great way to a feel of the city. The North End is a fun place to find some place to eat.
Boston is very walkable. I would recommend starting at the beginning of Newbury Street (at the intersection of Mass Ave), walking the length of Newbury Street, walk through the Gardens and Common and head down to Haymarket. From there it's a short walk up the Greenway to the North End. This will take you past many historic sites and the Freedom Trail.
Also, the commuter rail at South Station heads to Gillette and back on Sundays if you didn't know and weren't interested in tailgating.
I was just thinking the same- I would suggest that after the Common, veer left and go up through Beacon Hill (check out Acorn st) on the way down to Quincy Market (a bit tricky) then from Quincy Market, hook a left and work your way to the North End and if there's time, the Charlestown Navy Yard is a walk over the bridge away, to the North.