I'm not a huge fan of wings... well, I wasn't until I visited Buff's. Go on an off-night (no major sporting events), and you'll be seated and served quickly. Every type of wing they have is exceptional.
Simply amazing. I'm a Roast Beef Blues guy myself- the onions melt in your mouth, the beef is juicy, and the bleu cheese on top is melted perfectly on the sandwich. I'll be back!
My pick for "Biggest Fire Hazard I've Ever Seen" (go in and check out the thousands of business cards and bras stapled to the walls and ceilings), this bar is in my "Key West Top 3".
The music both during the day (usually a guy singing cover songs with his guitar), and at night (larger band on the big stage in the back), is always good. Drinks are cheap, and they have a couple of pool tables if you're into that, too.
Here's a game for Key West first-timers: When you walk up to this bar, look up, and you'll see a sign out front with a giant fish on top of it. Get yourself a quarter, stand with your toes on the curb directly in front of the sign (with your back to the bar), and try to arc a coin into the fish's mouth. Get it in, and... well... you lose 25 cents.
Other than that, it's your run-of-the-mill Key West Island-Style dive bar; go on in, have a drink, and take a look at all of the Capt. Tony memorabilia on the walls of the pool room.
Quitely nestled between two buildings, the width of the Smallest Bar measures about 7'. It's a bartender, four bar stools, and a cooler full of frosty beers.
It's a nice stop-off from Duval St., and there's usually good conversation from the bartender on duty. Definitely worth checking out if you're in Key West for any amount of time.
This is always a stop when I visit Key West. I've never hung out here for more than one drink, but they've got the best selection of frozen drinks in town. This is a good place for people watching, or beating the heat with the fans/misters they have installed under the bar's spacious canopy.
As for drink recommendations, I'm partial to the Rum Runner, or White Russian, myself. (Oh, and be sure to get a "floater" in any drink you order.)
I've had my share of blurry nights (and weekends) here at the Isle. It's cheap, it's divey, and the whole place is built around drinking.
The hotel is disgusting, but you probably won't care too much because if you're at Holiday Isle, you will not be hanging out in your room.
The site itself is well laid out- there are several bars on the property surrounding the hotel buildings. The food isn't bad; it isn't great, either. Their beachfront is nice to relax on, and they are neighbors with a number of charter fishing operations, so if you're into fishing (or renting a boat for the day), this is as good of a place as any.
If you're just passing through on your way from the FL mainland to Key West, this is a good "halfway" spot to pull over at to stick your toes in the sand and enjoy a cold one before hopping back on the road.
This is a great KW "locals" bar, off the beaten path of Duval St. Thankfully, most tourists don't know of this place, so it doesn't get obscenely crowded, just very crowded.
During the day, it's a great place to kick back and chill out in a relatively quiet open-air bar (free popcorn, too).
Good crowd, good music, and good times. I'll be back.
As blurry as my trips to Key West often are, this bar is definitely a must if you're in KW. Between JMH and the rest of the hooligans performing daily/nightly on their stage, you will definitely have a lot of fun singing/clapping along with the bands.
Downsides: service is slow, it's crowded, and there aren't usually any drink specials. Upsides: You're in Key West, so you're probably too drunk to notice any downsides.