Winter Park

Fun fact: four presidents have visited Winter Park, Florida, including Barack Obama in 2012. With those notable stop-ins, this former resort town exudes charm and encourages relaxation even today. The suburban city in Orange County showcases some of the best natural scenery in Central Florida, and nature lovers flock here to enjoy the more than 70 parks in the city. For those still looking for a resort feel, Winter Park also has top-notch golf courses and a popular shopping district.

The city’s Main Street is a lively area. It serves as a cultural hub, complete with art galleries, a liberal arts college, museums, a cemetery and even a beach. Boaters enjoy having easy access to a launch nearby, and two of Winter Park’s most famous attractions are Rollins College and the Charles Hosmer Morse Museum of Art. The latter destination is home to the United States’ largest collection of Tiffany glass.