Key West was fun the first two times...honestly, by the third time, I was "over" it. It's just sooo expensive, and everyone just thinks they're so "quirky" and shit. And forget about parking, you have to walk everywhere, which isn't too bad unless it's 95 degrees with 95% humidity. I DID love going to the Dry Tortugas, though. Best snorkeling I've ever done. I like the drive down to Key West, too. We stopped off at Bahia Honda state park, truly great beach, and I'm not even a beach person.
Last time we went to Miami, we didn't go all the way to Key West. We stayed in Key Largo, saw a shark about 10 yards off the beach. Went to John Pennekamp Coral Reef State Park and rented a boat again. Then we went to Marathon Key and had a nice time there. The Big Fish Grille in Key Largo has fish tacos that are not to be missed.
NEXT TIME I go to Miami/the Keys, me and Wifey will get a tattoo at Miami Ink!