Ok disclaimer, I kinda forget the names of the guides but I had three on the trip. Not going to talk bout the first 'cause we were only on his for one stop, but figured I'd talk about the other two.
I believe his name was Matty (or Mat..? sorry) but he was a really funny guy who kept it entertaining for everyone. Did about half the route with him, there was a lot of traffic moreso than the average 'cause I believe it was the last day of a festival, plus moving in college students,,, plus the big detour for construction. Point of saying that is there was a lot of moments of just sitting with nothing really going on, but he made it enjoyable by cracking jokes and keeping the good energy even for the few of us who were on that trolley at the time.
Also want to say if he happens to read this (if you don't remember that's fine lol), my dad was the one who kept laughing at like the 10 Dunkin's jokes and I found it entertaining enough, maybe you could try and make a guessing game of how many there are in a certain area if you ever have really bad traffic again haha.
Anyways next up we had someone who joked about a lot of different names so I'll just say he was the one who had a bag of toys to give out to some of the younger kids. We got on at stop 9 for him and wanted to go around the whole tour again without getting off at all this time, and he was great for that. Not only did he say the kinda scripted educational stuff, but he shared a lot of stories as well plus more up to date info on some other 'not-main' locations. Of course he was funny with it too, and this time around the entire trolley was full, but everyone was having a good time as well. Also props to him too with the traffic, it was later in the afternoon and it was even worse than before in my opinion, full standstill at one point with turning the corner taking a literal 10 minutes, but once again he kept telling new stories to fill the tim and I never felt bored.
The basic summary of those two paragraphs is that the guides I had were funny while still being educational. As someone who is more of a visual/hands on learner vs just textbook/scripted stuff, incorporating jokes into the info and actually making it feel more like a conversation out of it rather than just talking at you made me retain more than I thought I would, so thanks for that.
The only other time I've been to Boston was when I was a really young toddler and I genuinely have no recollection of it, so it was a great semi-first time experience for me. We only planned on going to the aquarium but last minute decided to do the tour as well, and I'd definitely recommend it if you have around an hour-ish to go and try it out !!