Re: The Caribbean Zone
It was a "tiki" bar located in a building decorated with corrugated tin walls on the outside nestled under the freeway. Closed in 2000 and even the site is unrecognizable due to ongoing work on the freeway/ramps/Transbay Terminal.
The interior was done up with tropical foliage and upstairs seating was the crashed fuselage of a small plane (the actual tour plane of the Doobie Brothers!). The windows were placed with monitors showing a loop of flying over tropical islands.
Unfortunately, the bar closed up just before the camera phone was common so there are precious few pictures online. But google for "caribbean zone" "san francisco" and you'll find a few, mostly of the outside. I was lucky enough to go a few times when I worked nearby in '96-'97. If I recall, the food was pretty good too - pupu platters, hawaiian burgers, chicken skewers.
Re: Indy-themed bar
I can't imagine them pulling off a "Club Obi-Wan". For starters, the name would make everyone think "Star Wars". For another, while a supper club is nice, it's not particularly adventuresome. I could maybe see them slapping the name on a rebooted "Adventurer's Club", reframed from the 1890s to the 1930s, but at that point it's a remix of Trader Sam's (Anaheim) and the proposed Jock Lindsey's. (To which I have no objection.)
(Okay, total tangent here. There's an underutilized space in Disneyland's Adventureland, previously the Tahitian Terrace (restaurant/show), now Aladdin's Oasis (mostly shuttered?), and occasionally used for Indy-themed events (Summer of Mystery shows, and the "IJ Adventure 20th" presentation). I know Disney wants more adult-themed dining options in that park, to the point of exploring serving alcohol outside Club 33 (gasp!). Perhaps someday they'll revamp that area back into a tropical restaurant, drawing on the '30s styling of Adventureland. Having seating that overlooked the Jungle Cruise much like the Blue Bayou overlooks PotC would be swell.)