Drive Time: Fifteen minutes northeast of downtown Orlando; ninety minutes northeast of Tampa
Long before greater Orlando was invaded by gloved mice and boy wizards—before Jurassic Park and Seuss Landing and all the rest—there was Winter Park. Founded in the 1880s by well-heeled Northerners as a balmy subtropical refuge, it remains a vision of lush prosperity on Orlando’s northeast edge: redbrick boulevards, moss-draped oaks, drooping banana plants fronting lakeshore mansions.
Known for its beacons of high culture, Winter Park is home to several standout museums (including the Morse Museum and the Albin Polasek Museum and Sculpture Gardens), an annual Bach Festival, and a huge springtime Sidewalk Art Festival. Rollins College’s leafy lakeside campus—with its Spanish Mediterranean stucco and red tile roofs, it could pass for a swank resort—has a small but impressive art museum of its own. Intriguing new sights have also sprouted up around town: innovative restaurants such as Brandon McGlamery’s Italian-inspired Prato, thriving artisanal start-ups like leatherworker Jason Gregory’s Makr Carry Goods, and a splashy new hotel that doubles as a cutting-edge gallery.
The 24-Hour Agenda: Owned by Rollins College, the stylish and dog-welcoming Alfond Inn sits just a few minutes’ stroll from Park Avenue. Amenities are plentiful, but the star attraction is the contemporary art—in the lobby, the corridors, even the men’s room. Another lodging option: the Park Plaza Hotel, a twenty-eight-room Old Florida throwback built in 1922 with balconies, jungly with potted ferns, overlooking Park Avenue.
After a sidewalk-table breakfast at the always bustling Briarpatch (try the smoked salmon scramble), allow time for a leisurely round of window shopping along downtown’s eminently walkable Park and surrounding avenues. (Check out Writer’s Block, a recently opened indie bookstore, and Orlando Watch Company, which carries new and vintage timepieces.) An hour or two perusing the Morse Museum’s dazzling collection of glass works by Louis Comfort Tiffany is all but mandatory, as is a lunchtime grouper sandwich at Winter Park Fish Company. The Saturday farmers’ market, centered around an old train depot, is a big draw. And the hour-long scenic boat tours, which shuttle you around three lakes linked by canals, are practically a local cliché but still a great way to gawk at grandiose houses at water’s edge. Maui B’s offers guided stand-up paddleboard trips through the chain of lakes, too, or a little farther north on the Wekiva River.
A short drive to Audubon Park (on the Orlando border)brings you to a welcome newcomer: East End Market, a food lovers’ bazaar hawking all things fresh and Floridian—from local microbrews on tap to cage-free duck eggs. Stick around for tapas at Txokos Basque Kitchen, where the tender, smoky pulpo gallego will change the way you feel about eating octopus. And treat yourself to a stroll around nearby Leu Gardens, a fifty-acre oasis of green tropical serenity; if your timing’s right, the Friday-night outdoor movie showings (April through June) are a locals’ favorite.
Meet the Locals: When James Petrakis was growing up in Winter Park, “if it was a nice restaurant, it was a steakhouse,” the chef says. The
town’s food scene has blossomed lately, largely thanks to Petrakis and his wife, Julie, who opened the Ravenous Pig in 2007 and have since racked up a string of James Beard Award nominations while growing their culinary empire, with a Southern-tinged, craft-beer-centered menu at Cask & Larder and a new “upscale bodega,” Swine & Sons.
“I wouldn’t want to be anywhere else,” says Anna Bond, who with her husband, Nathan, cofounded a homegrown success story: Rifle Paper Co., which they launched in 2009 and whose stationery, phone cases, and other accessories—graced with Anna’s illustrations—now appear in nearly five thousand stores worldwide, including Anthropologie and Barnes & Noble, in addition to the brand’s downtown headquarters and shop.