As the country's oldest city, Saint Augustine, Florida, has plenty of historic charm. Henry Flagler turned the town into a winter resort in the late 19th century, headquartering his Florida East Coast Railroad there. His influence can still be seen in the architecture of the buildings he constructed, such as the Ponce de Leon and the Alcazar Hotel, which are now City Hall and the Lightner Museum. Even modern homes here have adopted the Old Florida style, with wraparound verandas, an open floor plan that maximizes air circulation, and a metal roof with a cupola to allow heat to escape.

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