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This Winter Park institution has been showing visitors glorious lakeside mansions since 1938, when they were in their heyday of attracting wealthy snowbirds from the North. Three of Winter Park’s seven cypress-lined lakes, which are connected by thrillingly narrow, hand-dug canals, are explored in a 1-hour, 12-mile tour narrated by salty old fellas. The lakes are flat and relaxing, with plenty of bird life, and your guide will pay particular attention to the works of James Gamble Rogers II, a virtuosic architect responsible for many of the area’s finest homes. Among the high points is a glimpse of the modest condominium where Mamie Eisenhower spent her waning years and 250-year-old live oaks. You’ll find this charmer 3 blocks east of the shops on Park Avenue. Bring sunscreen because the pontoons are exposed.