My BiL is a Naval Academy grad. The Naval Academy experience is significantly different from every other service Academy because it's in a Capitol city that is fairly large. You walk through the gates and you're literally in Annapolis. I would say they only comparable experience is "The Citadel" for an SMC. I've heard a bunch of stories about how they'd rent hotel rooms in Annapolis and party, take off their uniforms and blend into the crowd.
West Point? There are bars in a few of the towns outside of Post, but the size of those places are tiny. Most of the cadets go to NYC to do their partying.
At VMI, even first classmen we could not be in public out of uniform. If we went to houses of host families or cadets whose folks leased places out in the county we'd often taken off our uniforms and put our gym clothes to be comfortable. But no one had civilian clothes unless it was a party that got a permit approved. Lexington, VA, had four bars at the time, a few more now, but it's still a tiny place. And the Commandants staff would patrol up town all weekend looking for drunken cadets.