A few months after I graduated from college, my fiance' (now wife) was working at a golf resort near Tampa. A good friend/co-worker of hers left the resort & took a position as an assistant manager at the Ritz-Carlton on the beach in Naples, FL. After he'd been there a month or so, he invited us & another young couple to come down for the weekend. We were all rubes from a small town in central FL; I'd never heard of the Ritz Carlton.
So we decide to go down for the weekend. We're going to the beach, won't need much - just some shorts, some t-shirts, a couple of bathing suits - all of which should easily fit in a small backpack. We make the 3 hour drive down there - of course, all dressed for sitting in the car for a few hours. Ratty t-shirt, gym shorts, flip-flops. We get to what we think is the hotel (this was mid-80s, so way before GPS); get a little worried because it looks pretty fancy for how we're travelling. We're sorta relieved that it is not where we're staying - we'd turned right & should've turned left. Go back out, spot the entrance marked for the RC. Head down the entranceway - a lavish, palm-tree lined drive with an immaculate yard & landscaping. When I see the doorman in his tux & top hat, I stopped in the middle of the road, we all looked at each other & laughed as my buddy says "OH SHIT." It's Friday night, there's some function going on in the lobby at which all the guys are in tuxedo, the ladies in ball gowns. Holy hell did we feel out of place. Might as well have been driving a damn turnip truck.
So that's probably the fanciest place I've stayed, but I've stayed at a number of dive lodges in 3rd world countries that were far more enjoyable and waaaaaaaaay cooler.