If you want to stay right around Boston Harbor, there’s lots of fishing to be had, then you should get a copy of Jack Gartside’s “Fishing Boston Harbor” by going to the eponymous website and ordering. This book will tell you tons, one hint though would be that Jack chose to live in Winthrop, which is a peninsula on the north side of the harbor and has quite a good variety of spots in close proximity, that’s where I go when in the area, and Jack’s book explains how to fish the spots.
JC