From its shops and bistros to its festivals and farmers' markets, the tony town of Winter Park has long been a hotbed for moneyed snowbirds and visitors, though lots of locals frequent its quaint cobbled lanes. Folks enjoy the commerce, no doubt, but also its color and space, whether in the form of flower boxes and tricking fountains or fine, al fresco dining.
See & Do
Park Avenue may be the most obvious and well known spot that's rife for Winter Park exploration, but visitors will get an altogether different POV on the Winter Park Scenic Boat Ride. From the city's beautiful homes to its flora and fauna, its a relaxing, lovely ride from end to end.
Whether your interests run horticultural or culinary, the Farmers Market is a dont-miss. Held ee Saturday morning at the city’s restored train depot, it channels the city’s heritage, and serves as a wonderful jump-off point to hit some of the area's cultural offerings like the Charles Hosmer Morse Museum. Once your appetite's worked up, consider a stop at Croissant Gourmet, Umi or perhaps Prato, for a posh cocktail and perfect pizza.
Feeling oenophilic? You can't do better than Park Avenue's Wine Room, where tasting fun (and comfortable seating) beckons. Clandestine? Consider Park Social. It's a speakeasy, so be sure you know the password. How about a movie? The nearby Enzian Theater is ground-zero for independent films, cult classics and has a fabulous bar/restaurant right on site.
Many visitors choose Winter Park as a small-town alternative destination to downtown's bustle and the crowds the theme parks draw. Consider a stay at the Alfond Inn, where on-site dining at Hamilton's Kitchen is a wonderful precursor to an evening of on-foot exploration. The verdant terrace at the Park Plaza hotel puts visitors right in the middle of everything that makes Park Avenue worth visiting: shops, restaurants, nightlife and more.
Park Avenue is Orlando's Rodeo Drive, lined end to end with brands visitors will recognize (Lilly Pulitzer, Lucky Brand, Restoration Hardware) and one-of-a-kind specialty boutiques for home, garden, jewelry box and closet. Even Fido will find a haven at The Doggie Door (and Fido's mom or dad can shop for wine and home furnishings simultaneously)!