For a sunset cruise I would recommend Sunset Watersports sunset cruise on their yacht, the Party Cat. They treat their guests fantastic and is a very enjoyable experience. Dont be afraid to ask the crew and captain questions about the island or their local hangouts,they'll usually be glad to share. Yes Key West is like New Orleans in the sense that you can walk down the street while drinking an alcoholic beverage...from bar to bar on Duval street all night long. Beach wise, the Simonton street beach is a pretty nice LITTLE beach with pretty sand, but sometimes it is just over run by homeless people. Fort Zachary Taylor has a pretty nice beach also, but the best beach is probably on Sunset Key...its the little island right off of Key West that has all the expensive looking houses and such. Hope this was of help to somebody.