Winter Park

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 nine-hole golf course is on the National Register of Historic Places.