The Florida city of Winter Park is a relatively upscale community north of Orlando surrounded by picturesque lakes. On the day of our visit there were showers in the morning, so we wandered through some shops and eventually had an awesome lunch at Bosphorous. After that the sky brightened and we were able to take one of the scenic boat rides. Earlier in history, the natural waterways connecting many of the lakes were expanded into navigable canals to facilitate transport of logs from lumbering operations. These now provide recreational boating opportunities.

There are several museums in Winter Park, but alas, we learned they weren't open on Mondays.
The Albin Polasek Museum & Sculpture Gardens
The Morse Museum of American Art, includes the world's most comprehensive collection of works by Louis Comfort Tiffany.

For a pleasant outdoor experience, the Scenic Boat Tour is recommended. We traveled by pontoon boat through three small lakes connected by canals. The lakes are surrounded by gorgeous homes, and on Lake Virginia we find Rollins College, a private, coeducational liberal arts college, founded in 1885.