Madeira Beach, Florida has quite the reputation; legend has it that the first settler of this small town outside St. Petersburg was in fact a pirate by the name of John LeVique. Although today Madeira Beach, fondly known by some as “Mad Beach,” sees many more tourists than pirates, it has not lost its sense of fun and adventure. Check out John’s Pass Village and Boardwalk, a large outdoor space with options for dining, drinking, and shopping, while the beaches along the coastline offer endless opportunities for relaxing and sunbathing. The city is also famous for its excellent seafood scene, with grouper being the town’s main specialty.

Rating: ⭐⭐⭐⭐⭐

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