It's criminal not to have Green Parrot at the top of the bar list. It's not just the best bar in Key West. It's the best in the entire country. I've never seen a place that punches so far above its weight when it comes to booking live music.
I also disagree with most of the restaurant list. Key West suffers from the same problem as Hawaii -- since they have a captive market, most places simply don't try very hard. It is better to go with the less-expensive joints like B.O.'s, Schooner's and El Siboney. The food is solid, unfussy, and not overpriced. Mo's used to be the epitome of this in Key West. Then Mo and Rena retired. Hasn't been the same since. Furthermore, so many of "the good guys" have shuttered -- Turtle Kraals, Waterfront Market, Bistro 245. We had breakfast -- con leche and cheese toast -- every morning at Sandy's Cafe, which became the best in town when La Dichosa closed.
I have no problems paying a lot of money for an outstanding meal. But with some of the prices Key West is charging, I expect a couple Michelin stars on the door.
Key West is better about using local fish than Hawaii is, though. There's that, at least. Still, too many places are pouring frozen food from a bag straight into a deep fryer and charging top dollar. Such places are counting on their customers not knowing any better. And the faster these restaurants are run out of business, the better.
Last time I returned home, I ate at the Conch Fritter Stand at Sunset Celebration, Schooner's, El Siboney (twice), and Dion's Quick Stop fried chicken. All the rest of my meals were prepared at home -- that way I knew where the hogfish and shrimp came from.
It truly breaks my heart that this is the state of affairs in Key West. In my youth, the bar happy hours were throwing down outstanding food for the cost of a beer -- Viva Zapata's, Bogart's, and Schooner's had better food than what you can get at most of today's restaurants. In addition, we had all those above restaurants which have since closed. And innumerable others such as Cafe Alia, Louie's Backyard, Goldie's Conch Salad. It's terrible to watch your home slide into decline.