Winter Park looks quiet on the surface, but beneath the brick streets and lakeside parks is one of Florida’s most influential cultural cities. This episode takes you beyond the café patios of Park Avenue and into the deeper story of how a small, carefully planned community became a powerhouse of art, architecture, and historic preservation.

We explore the city’s origins in the 1880s, the citrus empire that vanished overnight, and the reinvention that followed. You’ll hear how Rollins College shaped national conversations, why a world-class Tiffany collection ended up in a small Southern town, and how Hannibal Square changed the political history of Florida in ways most visitors never learn.

Think of this as a guided walk through a place that hides more truth than its postcard image suggests. Winter Park is elegant, thoughtful, and far more important to Florida’s identity than most people realize. By the end, you’ll understand why this small city has shaped taste, culture, and conversation for more than a century.

Wherever you go, you can take the story with you.

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