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27. Florida

If most people were asked to name a state they most closely associated with the word "retiree," many would say Florida. The state's beaches have drawn in more retirees than some states have people. However, that has been a double-edged sword. Taxes remain relatively low, with a sales tax of 6%. However, few small beach towns still exist, and most places see huge influxes of tourists during the summer months. Also, all the condos look identical.

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That said, the state is pretty big, and it's still possible to find old Florida vibes if you know where to look. The southern portion of the state also offers retirees a more Caribbean vibe. Florida's population is around 22.2 million, with 4.7 million being 65 or older.