Park Avenue, Orlando

Winter Park was founded in the late 19th century by northern business magnates as a resort community. Henry Plant’s railroad had connected Orlando and Sanford with the Atlantic coast rail lines, and visitors were flocking in. Northerners came down to thaw out and to recuperate from various maladies. A spot along the railroad tracks, nestled between several beautiful lakes, caught the eye of Loring Chase. Together with a group of wealthy friends, they planned out the town and promoted it heavily. It eventually became the site of Florida's first four-year college, Rollins, and of the communities crown jewel, the Seminole Hotel, a long-gone luxury resort.

To further attract vacationers, the city planners borrowed some themes and names. And so was born the second-most famous Park Avenue in the US. You won't find quite the same amount of hustle and bustle here as on New York's version, but you will find shopping and dining with a cozy village vibe. Along the avenue, you'll find Central Park, with a stage on one end for local events and a beautiful rose garden.

If you have time, check out the pontoon boat tour. It's an excellent way to see the city via the many canals that connect the area's lakes. Knowledgeable and humorous tour guides fill you in on the community's history and happenings along the way. Most of Winter Park's attractions are centered around Park Avenue, making the city a great place to stroll around. You'll find the Morse Museum of American Art, Casa Feliz Historic House Museum, Rollins College, and a history museum along the avenue.