I've never done a pubcrawl, though what you describe above sounds like a memorable experience to try at least once. I just got a drybar for my house and I plan on breaking it in hard. I'm a homebody anyway but the drybar just solidifies the fact that the bulk of my imbibing will happen at my house. I am still scouting for 2 items and then the living room redo is complete. The bar looks awesome, I will have to post a picture of my amazing find when the place is completed.
Therapy should first be about the relationship. If you're not vibing with this person move on. If therapy goes well you'll be sharing with them a lot of things and if there's room for humor, for relief, for intimacy this person is right for you. Finding the right therapist is about finding someone you feel comfortable with and who has the expertise in whats going on with you. Its not about the degrees they have, its doesn't have to be an authoritative relationship. A good therapist should be able to provide what you're looking for. If you're looking for someone to be a good friend they can be that, if you're looking for a more straightforward person thats possible too. I'd say move on from this person because it seems to me like you're not getting much out of it and they aren't providing what you need.
In my wife's case, it's her sister who does these things. She's the constant tag-along. The last "art" she brought home she held it up and said "I don't know what the fuck this is but we just spent $40 on it." My daughter asked to have it. Not as art, but to use as the "living room" wall paper for her doll corner. Tell of this new lameness of which I am yet to be informed of. I've done pub crawls before. Which on average involves 8 to 12 bars but the time you hit bar six everyone's like "Fuck this, fuck these fags, let's do our own things" and everyone goes off into the night wearing some loud t-shirt that says "HYMAN & THE SHITPUSSIES FUCKCRAWLAPOOZA '16: NIGHT OF RECKONING" or something like that.
Think of a trolly totally powered by people peddling (similar to a bicycle). People take it on bar crawls. It goes roughly 3 miles an hour and clogs up traffic. It's really stupid. I have prefered the traditional way, walking.
I see what katokoch has means by fun on paper. I have seen that once. Maybe if you weren't doing physical labour while drinking.... But just being toured around in a small outdoor pub....that would be cool. Pedalling a bike? Fuck that, son. Bikes aren't for drinking, they're for hurting yourself.