Going to jail is never fun: dudes inside are scary, there's no TV, and the narrative arc isn't quite as strong as the time you saved Christmas. Or went to camp. For a new Bay Area-themed vacation destination even Jim Varney would've dug, check out Germany's Alcatraz Hotel
Located just 45 minutes outside of Frankfurt (direct flights from SFO!), AH is an honest-to-God former German prison that's been turned into a 56-room, SF-referencing hotel with actual converted cells as sleeping quarters, choice amenities (flatscreen TVs/24hr room service, etc.), and sorta-choice prison amenities like barred windows, a toilet in the corner of the room, and a steel door slot used to slide in your dinner known as a "piehole", which is also what Kirstie Alley calls the giant fridge in her basement. Rooms offered range from a bare bones "cell room" (a partition-less box with a single bed/desk/toilet/sink and communal showers in the hallway), to "prison suites" (California King/plasma-equipped lounging room/fully equipped private bathroom), and'll run you anywhere from 49-159 euros a night, which is about the range you'll find on a nightly basis at Ruby Skye. The nearly 150-year-old building also includes a full jail-sized pub in the lobby called the Hinter Gittern (which's German for "behind bars"), plus there's an inmate dining hall/ballroom (with the requisite blown-up Golden Gate Bridge photography on the walls) that'll hook up an included-with-the-room continental breakfast buffet, which may or may not include boat drinks, and cheeseburgers in paradise.
And because no prison-themed hotel would be complete without it, they'll even throw in a pair of black-'n-white striped pajamas with your name embroidered on the back -- just be careful they don't accidentally switch those jammies with a death-row inmate who looks exactly like you, but talks with a much lower scarier voice.