It doesn't quite count, but I've spent in total a couple of months on the inside as a public defender. Still, I've been searched, frisked, wanded, and passed through all sorts of metal detectors. I've been in juvenile facilities, maximum security, psychiatric prison facilities, the works. It was interesting for awhile, but the corporate grind is better.
My favorite jail was the law library in Deschutes County, Oregon. When they closed the old jail under the Courthouse, they moved the law library in there. I had a card key to get in whenever I wanted, so I often did a lot of research down there. They left it more or less intact, as well. Always a fun visit.
Got arrested once, for what looked like manslaughter. Happened after a car accident. The other guy pulled through, somehow, but they thought he was going to die, so I was arrested and taken in for urine and blood samples while they did a reconstruction. Turned out the other guy was over three times the limit in addition to drugs and he ended up in prison for the accident. My tests came back clean. I wasn't booked, charged or even given a ticket. Have to say that the police could not have been nicer during it. Really. They were actually nice.
Other than that, 5 speeding tickets, 4-5 parking tickets and a fix-it ticket for a missing front license plate.