Long before Orlando’s theme parks, Northern snowbirds flocked to Winter Park for its mild climate amidst scenic lakes and moss- draped live oak trees. Today, the area’s charm draws visitors yearround with its art museums, sidewalk cafes and local boutiques.
Start on the southern end of Park Avenue at Rollins College, Florida’s oldest college that rests on beautiful Lake Virginia. Then, work your way up the half-mile stretch of cobblestone to peruse the shops and eateries. You’ll find everything from a two-story Pottery Barn inside a 1939 art- deco movie theater to locally owned boutiques like Violet Clover, Shoooz, Tuni and Tugboat & the bird.
Treat yourself to a coconut ice- cream cone at Kilwins, chocolate- covered popcorn at Peterbrooke Chocolatier or savory samples at The Ancient Olive. The Wine Room is another cozy spot for a shopping break, where you swipe your credit card for 1, 2.5 or 5- ounce pours.
Just past Central Park, the Morse Museum of American Art bookends the shopping district on the north end of Park Avenue and features the world’s largest collection of Louis Comfort Tiffany glass, including his famous chapel from the 1893 World Fair in Chicago.
If you don’t have time to see the museum, duck into the Alfond Inn on the way back to the car. Built by Rollins College, with famous residents like Paul McCartney, the Alfond Inn also serves as an art showcase with contemporary works on loan from the campus’ Cornell Fine Arts Museum.