Our neighbor, Winter Park, can’t be called a neighborhood – it’s its own city, made up of neighborhoods just like Orlando. There’s the well-established, swanky commercial strip of Park Avenue, the up-and-coming Hannibal Square, and various homey pockets long loved by locals. Park Avenue is the place to start, though. Packed with restaurants and boutiques, it’s anchored at its tree-lined north end by the renowned Morse Museum of American Art (445 N. Park Ave., 407-645-5311, morsemuseum.org), a repository of Tiffany glass and Victorian artifacts. Le Macaron (216 N. Park Ave., 407-295-7958, lemacaron-us.com), hidden away in a brick courtyard, is one of the few places to find the crisp-shelled Parisian sweets in the area. Barnie’s Coffeekitchen (118 S. Park Ave., 407-629-0042, barniescoffeekitchen.com) will caffeinate you with single-bean pour-overs and carefully crafted lattes, along with an updated menu (try the shakshuka, eggs baked in tomato-thyme sauce, if you have time to linger). For creative cocktails, the lounge at Luma on Park (290 S. Park Ave., 407-599-4111, lumaonpark.com) is a cozy alternative to the bustling dining room. Just off the avenue, Cocina 214 (151 E. Welbourne Ave., 407-790-7997, cocina214.com) serves high-end authentic Tex-Mex in style.
Although national retailers – Gap, Eileen Fisher, Lilly Pulitzer, etc. – are well-represented on Park Avenue, the independent boutiques offer better service: The ladies at Thread (356 S. Park Ave., 407-622-7600, threadwinterpark.com) will help you put together an outfit from racks packed with Tory Burch, Tracy Reese, Splendid and Calypso, and keep you posted on upcoming sales with handwritten notes.
The leafy, cobblestoned streets of Hannibal Square enfold a choice selection of cafés, bistros and shops. A glass of wine at Dexter’s (558 W. New England Ave., 407-629-1150, dexwine.com) is a classic beginning to your stroll; whimsical letterpress stationery can be found at the charming, tiny home of Rifle Paper Co. (558 W. New England Ave., 407-622-7679, riflepaperco.com) along with carefully curated housewares and accessories. Speaking of tiny, the deliciously eclectic menu at Fresh (535 W. New England Ave., 321-295-7837, freshcafe-wp.com) shows chef Gina Bugayong’s unbounded creativity. You may bump elbows with your neighbors in her rustic-modern jewelbox of a cafe, but you won’t mind.
Where Fairbanks Avenue splits off from North Orange, Floyd’s 99 Barbershop (610 W. Fairbanks Ave., 407-790-7799, floydsbarbershop.com) offers straight-razor shaves and old-school cuts in a rock & roll atmo. Further west on Fairbanks, traffic roars past a true Winter Park treasure – Skycraft Parts & Surplus (2245 W. Fairbanks Ave., 407-628-5634, skycraftsurplus.com), marked by a flying saucer on a pole, is where you’d go if you were in fact attempting to build a flying saucer. It’s packed with bins full of switches, screws, gears, and incomprehensible bits of plastic and metal and felt that could be the basis of a great machine – or a great art project. Most impressive is the way the ladies behind the counter recognize and know the price of everything. Nearby sits Orlando Vintage Clothing Co. (2117 W. Fairbanks Ave., 407-599-7225, orlandovintage.com) a source for impeccable 1950s and ’60s fashion. On the same block, B&B Junction (2103 W. Fairbanks Ave., 407-513-4134, bbjunction.com) serves high-quality organic and local burgers.
Near the intersection of Semoran Boulevard (aka 436) and University Boulevard sits Full Sail University, an entertainment media school with roughly 8,000 on-campus students. That many kids on a 24-hour schedule (not to mention all the instructors and staff) mean there’s no shortage of fast food, but there’s also some homegrown charm to be found. Humble little cafeteria Rincon Cubano (3327 N. Forsyth Road, 407-679-5600) slings some of the best Cuban food in town – their cortadito will change your life, or at least your day. Sleeping Moon Café (4951 N. Semoran Blvd., 321-295-7844, facebook.com/sleepingmooncafe) is a relatively new addition featuring coffee, sandwiches, local art and open-mic nights; vegans will find good choices here. And you can dunk anything from live blue crabs to sliced beef to baby bok choy in the simmering hot pots at newcomer Hotto Potto (3090 Aloma Ave., 407-951-8028, hottopotto.com), before slathering with their array of house-made sauces.
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