The Wicked Stepsister

I'm not a local, but I visit my parents in South Orlando a few times a year and am always in search of a decent watering hole--specifically in the hit-or-miss Kissimmee area. My friends and I had a really unexpectedly good "guys night out" at Wicked Stepsister. The place reminded me of some of the cooler LA dive bars, like Barney's Beanery.

The Wicked Stepsister has a cool laid back vibe. These guys had a strong selection of beer and wine, which made up for the lack of spirits on the menu. Maybe that's something they'll incorporate later on, but no biggie for us. Just tell the server or bartender what you're in to, and they'll make spot-on recommendations for beer or wine. The free pool was an unexpected bonus, so my buddies and I enjoyed a few games.

The service was super-cool and friendly. Very knowledgeable and made great recommendations about the beer, played any music we requested, even offered us cigars.

The location is in a cool area, too. I really liked the historic district; haven't been out here in years. Definitely worth checking out, if you're looking for a relaxed atmosphere with a great selection of beer and just an overall cool vibe. Highly recommend!

Service so rude we left before ordering.

They also only have beer or wine, not a full bar.

For some reason this venue is all of a sudden showing up as 3 Sisters Speakeasy.  This isn't 3 Sisters, it's the dive bar across the street call The Wicked Stepsister.  Hopefully Yelp will get this fixed.

Anyway, I just wanted to say that what you ask for is exactly what you get here.  Super dive-y, super smokey bar with a jukebox and a couple of pool tables.  They also had a DJ out front for a couple of hours last night, which seemed a bit random.

As a stand-alone property I'd say you needn't bother.  However, as an adjunct to the four venues at City Centre (3 Sisters Speakeasy, Sushi by Chef Ha, Vintage Vino, and Chef John's Dockside Inn), it really fills its role well.  You definitely get the sense that the location, and its patrons, were rejected by the we're-too-good-for-you crowd across the street.  Although I'll probably never go in here again, I am pretty impressed by the story.  

Ah heck, maybe I'll go back next weekend, just to see if I can get a deal on a hookah.