For great entertainment and the premier "straight bar" stop by Sloppy Joes. We actually stopped there twice during our day in Key West. The best time to stop was in the evening when they have their entertainment. One of the regular warm up acts are 2 guys who are definetly not politically correct. Make sure you listen as they describe all the other bars in the area.
There is three entertainment/bar areas to find something for everyone.
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