You should call Stoddard's, Firefly Outfitter's, or Orvis Boston for a guide referral. There are much cheaper ways to catch fish in the city though. There's Wollaston Beach in Quincy, Castle Island in Southie, Charlestown Navy Yard, UMass Boston, and of course the Boston Harbor Islands. For $7.00 you can get your ferry pass and access the best fishing in Boston. If you do get a guide, make sure he/she goes further out than the airport. I had the worst trip of my life in the harbor when all we did was fish beneath planes landing and taking off.