This peaceful, upscale community may be just outside the hustle and bustle of Orlando, but it feels like a different country. The town's name reflects its early role as a warm-weather haven for those escaping the frigid blasts of Northeast winters. From the late 1880s until the early 1930s, wealthy industrialists and their families would travel to Florida by rail on vacation, and many stayed, establishing grand homes and cultural institutions. The lovely, 8-square-mile village retains its charm with brick-paved streets, historic buildings, and well-maintained lakes and parkland. Even the town's bucolic 9-hole golf course is on the National Register of Historic Places.
On Park Avenue you can spend a few hours sightseeing, shopping, or both. The street is lined with small boutiques and fine restaurants and bookended by world-class museums: the Charles Hosmer Morse Museum of American Art, with the world's largest collection of artwork by Louis Comfort Tiffany, and the Cornell Fine Arts Museum, on the campus of Rollins College (the oldest college in Florida).
Winter Park at a Glance
Sports and Outdoors
Elsewhere in Orlando
Need a break from the big city? View 42-hour itineraries from 13 cities.More