One of the best ways to appreciate the under-the-radar beauty and classic Florida escape of Winter Park is to meander over to Lake Osceola for a one-hour boat tour. You learn much about the area's history and gossip about the houses on the lake. Hop on an 18-passenger pontoon and cruise through Winter Park’s tropical canals and lakes, past mansions, Rollins College and other sights.

If you’d rather explore on your own, they also rent canoes and rowboats