Trial run - concept - 2 or 3 bars and dinner center city

Meet at a place (TBD - Red Owl Tavern?), have one drink, and move to the next place (TBD - Victoria Free house). Decide if we want to try a third place, or stop to eat. Maybe eat at one of the places we visited, or go somewhere fun (Fogo de chau)
Its all conceptual at this point. I'm looking for feedback on the best bars, best food, and realism of such an evening. I do have a concern about the group size making it all unmanageable, so I'll limit that (maybe 6 or 8 ).
Is there any interest out there?
I expect it will not be a cheap evening out, particularly if we use a lot of Uber.
If I had sufficient interest, and people were willing to kick in maybe I'd rent a limo for the group.
I'm still defining the event so any date is simply a placeholder.