Making "Drone"
I quickly came up with two places that I thought could be interesting. Both were far enough away from Logan to be uncontroversial. Better still, both were large enough open spaces that I would probably be able to fly the drone safely. And finally, both had recognizable enough landmarks that I would be able to put Benjamin and Jeremy into a shot that people (at least people familiar with Boston) would recognize.
The two places were Larz Anderson Park in Brookline and the Middlesex Fells Reservation just north of Boston. Larz Anderson Park has a very recognizable temple in the center of the park that would make for a great photo if shot from the air with Benjamin and Jeremy inside:
And the Middlesex Fells Reservation has a tower that would look great from the air.