Tommy,
I was at a wedding in Boston last month. We stayed at the Millenium Bostonian Hotel at 26 North Street across from Faneuil Hall Marketplace. Right next to the hotel is a nice cigar lounge with a walk-in humidor (somewhat limited selection). I can't remember the name of the place.
I also went to the Gloucester Street Cigar Company at 34 Gloucester Street. They have a small smoking area in the front of the store and Jose, the new owner, is very friendly and enjoys talking cigars. He gifted me an LFD L400 Oscuro Natural and a DL Chiselito. Of course, I couldn't resist buying a couple of other sticks.
The Captain at the Millenium saw me returning with my purchases from Jose and struck up a conversation. Turns out that he knew Jose. The next day he gifted me an Opus X and a Davidoff Millenium. He was obviously a true BOTL and in return I left him one of the Padron 26s I had purchased from Jose.
Hope that you have a good trip and encounter a few BOTLs as I did.