Bobby’s Monkey Bar

I’m realizing quickly that hanging out with the locals/​semi-​locals, you see a whole different (and frankly interesting) side of Key West. This bar is nestled among the residential areas of Key West back in a neighborhood.
This was the first stop after flying in that afternoon and it was time for a cocktail. This bar did not disappoint. Small and dark, it was definitely a little dive bar, but in a somewhat charming sort of way. Cash only, but if you show up without, they have an ATM right there.
Drinks were cheap and plenty strong. They have a u-​shaped bar right inside the door, but if it is full, there is a rail that runs around the place where you can set your drink and talk. They also have a pool table in which several friends took part.
If you’re looking for a cheap drink with a kick, this is your place.

One of the things everyone kept telling us before we went to the Keys, especially Key West, was how gay friendly it was. Being a gay couple on our honeymoon this was an extra win for us. I quickly pulled up Unilocal and searched for places I wanted to go.
I chose Bobby’s Monkey Bar because it wasn’t a big tourist bar. I much prefer the small, more dive bar feeling places to the gay clubs.
After wandering around for a bit we were hot and in need of a cold drink. We just happened to be a block away from Bobby’s. We went in and got (almost) exactly what we were looking for. It was a small, smoky, and very loved place. It was only the bartender and a usual at the bar. It was perfect for my husband because he is a social creature. He was bursting at the seams to talk to someone. We spent 2 hours in that bar talking to the bartender about Key West and what to do.
The bartender explained that while this bar technically could be called a gay bar, over the years it has morphed into more of a locals bar that just happens to have a lot of gay patrons. It was the model of a neighborhood bar. People came and went quickly. Mostly they were just dropping by on a walk to say hi to the bartender or to drop things off for later.
Everyone was very welcoming to us too. I think that many people touched on the fact that they got a odd vibe from the locals. I think that odd vibe is the want to preserve their local bar. It is like having a secret surfing spot. Once everyone knows about your spot they all want to come. I think they have a fear that non locals will be rowdy drunk tourists that walk Duval street, or that their little piece of quiet will be disturbed. Show them respect and that you aren’t some drunk ass and you will be just fine.
Bobby’s made our day with a quiet afternoon, good drinks, and excellent conversation. A hidden gem that deserves respect and patronage.
⁸⁸⁄₁₀₀

Our B&B manager told us this was the «locals» watering hole. Down the street and we walked by, sat on a bench across the street and decided that we were probably to touristy to go in.

Wonderful people
Great a karaōke
A local bar so don’t expect Hollywood but
Great crowd
Friendly bartender live crowd
I love it the first time
Will be back if in key west again

Definitely a place the locals congregate at, but tourists are welcomed with open arms. Bartender is awesome and fast. We went on a Tuesday night, and they were doing karaōke. (Not sure if it’s only on certain days or if it’s a nightly thing.) Karaōke host was great. Everyone in there was really cool, crowd was a lot of fun. Cash only, but there is an ATM on site.

This place could be a lot if fun, but there’s limited seating. Unless you’re sitting at the bar, you have limited interaction with others. Our bartender wasn’t particularly friendly or outgoing, either.

This place was so much fun! As a straight person, you definitely need to be thick-​skinned to some uncomfortable glares, but for the most part, the staff and crowd were friendly and accommodating to us «out of towners.» Expect a low-​lit, dive bar atmosphere with a very attentive bartender and a phone book thick book of every karaōke tune. Guaranteed fun time!

Got in late to Key West. and walked to the closest bar for a drink
Walked into Bobby’s Monkey bar.
Now this is an old school Bar. Pool Table, Smokey, and pouring strong drinks.
Of course. Thursday nite was Karaōke night. I’m not a singer but just had to join in the fun. what was going to be a few drinks turned into a few hours of a bunch of fun with new friends. Hah
The locals were great and are straight friendly. This bar is a little bent to the left but… like Homer Simpson said. I like my Beer Cold and My Homosexuals Flaming. but it’s Key West…