Ever since the early 1960s, when Walt Disney chose Central Florida as the location for his most extensive theme park, Walt Disney World, Orlando has been synonymous with mouse ears, thrill rides and daily parades. But most locals readily divulge that fantasy fulfillment has little to do with the real life of urban Orlando. From the downtown region heading north to well-to-do Winter Park, the city is a checkerboard of intriguing neighborhoods filled with historic bungalows, interesting galleries and cafes catering to the creative class. Nature is also a central attraction in the lake-filled city and suburbs that include warm springs preserves and parks with live oak stands. The glass-walled Dr. Phillips Center for the Performing Arts, opened in 2014, has given downtown a cultural bump, while homegrown creative endeavors include a new orchestra devoted to modern classics and unstarched performances.
Friday: 1) 3 P.M. Digital Art Dive
Make the Orlando Museum of Art your first stop in erasing theme park stereotypes. It holds an engrossing collection of American art, including paintings by Thomas Moran, Georgia O’Keeffe and John Singer Sargent. But its contemporary galleries, featuring digital artworks by artists like Jennifer Steinkamp are, perhaps, most compelling. The museum annually awards the Florida Prize in Contemporary Art; last year’s finalists dealt with issues from social justice to violence in Syria. A new show, “State of Excellence: Treasures from Florida Private Collections,” runs through April 29, and focuses on European and American art.
2) 5 P.M. Aperitif With Atmosphere
Set design does not begin and end with Disney, as the new Mathers Social Gathering lounge testifies. The downtown speakeasy-style bar resides on the third floor of a 19th-century furniture store. Patrons must find the hidden door in the foyer’s bookshelves to gain entry to the cavernous room with exposed brick walls and beams and conversation areas anchored by tufted leather couches and steamer-trunk coffee tables. Go at happy hour before the club-hoppers flood the place to indulge your design appreciation over a gin-and-cucumber Mathers Fizz and a bowl of roast fava beans served on silver platters.
3) 6 P.M. Taco Time
Tacos have hijacked the Orlando culinary scene with a string of newcomers from downtown’s Tin & Taco to the bustling Reyes Mezcaleria and the mural-covered Hunger Street Tacos in Winter Park. But if you can only hit one, make it Black Rooster Taqueria. The narrow, elbow-shaped space offers open views into the kitchen where chefs press corn tortillas to order while frying up pork fat, the centerpiece of the menu’s most indulgent taco and searing carne asada. There are also fresh limeade specials, guacamole made to order and brothy bowls with slow-cooked meat, including pozole verde. The limited service system – order at the counter and runners find you with the food – means you may not linger, but you’ll leave satisfied.
4) 7:30 P.M. Orchestral Maneuvers
Follow the creative crowd to whatever is happening at the Timucua Arts Foundation. Founded in 2000 by Benoit Glazer, the music director for the Cirque du Soleil show here called “La Nouba,” Timucua stages more than 70 events each year, most of them free, most of them concerts and many of them in Mr. Benoit’s living room, which is expansive enough to seat 99. It recently launched the new 15-piece Alterity Chamber Orchestra as its ensemble-in-residence. The orchestra presents contemporary classical pieces with passion, but without the formality normally associated with classical concerts.
5) 9 A.M. D.I.Y. Neighborhood Tour
Picket-fenced bungalows, moss-laden trees and brick-paved streets fill the historic residential neighborhoods of Thornton Park and Lake Eola Heights to the east and north, respectively, of downtown Orlando’s Lake Eola. Take a D.I.Y. tour to get a feel for Old Florida life aboard one of the orange bikes in the Juice Bike Share program. Make your first stop Downtown Credo coffee, a social-impact-oriented shop with four locations around town that sources coffee direct from growers and asks customers to name their price for each cup. Make sure to walk that bike around Lake Eola: Bikers are forbidden from cycling on the sidewalks that ring the shore.
6) 11 A.M. House & Garden
In the 19th century, old-money snowbirds from the north began spending their winters beside the lakes of Central Florida, particularly Winter Park, the Orlando neighbor that feels more like a village than a suburb. They and modern-day successors built mansions lining Lakes Osceola, Maitland and Virginia, which are connected by old logging channels: narrow passages about the width of the 18-seat pontoon boats operated by Scenic Boat Tour. The tour company’s hourlong itinerary takes in the fine homes and the Spanish-Mediterranean-style campus of Rollins College. The excursion is also a nature tour, especially in the slim canals where guides point out a 150-year-old live oak, among other sights.
7) 1 P.M. Double Feature
One of Winter Park’s affluent part-timers was Charles Hosmer Morse, whose heirs eventually amassed the largest collection of glass works by Louis Comfort Tiffany in the world and made it the anchor of the Charles Hosmer Morse Museum of American Art. In addition to wall-size, garden-themed panels, the museum’s Tiffany collection includes the kaleidoscopic chapel he created for the 1893 World’s Columbian Exposition in Chicago and several rooms from Laurelton Hall, his Long Island estate. For contemporary ballast, cross the leafy Rollins College campus to the Cornell Fine Arts Museum, which mounts shows with pieces that range from old master paintings to modern-day neon.
8) 4 P.M. Pushing Paper
If you’ve shopped in a hip stationary store recently, chances are you’ve seen the festive and funky designs of Rifle Paper Co. The Winter Park design firm operates an airy boutique in the Hannibal Square neighborhood, where you can pick up everything from cards and journals to wrapping paper and iPhone cases in its signature floral patterns. A few blocks east on Winter Park’s main drag, Park Avenue, independent boutiques include Violet Clover, selling blouses and accessories; and Han Design, with unique jewelry and Turkish rugs. Grab a novel and flop down in a cozy armchair at Writer’s Block Bookstore, where the staff tapes their mini book reviews to the shelves.
9) 6:30 P.M. Progressive Feast
Getting around much of Orlando requires a car, but Winter Park offers a bounty of restaurants within walking distance of each other. Start at the Ravenous Pig, staffed by crack bartenders who whip up cocktails that may include a rum-port-spiced apple Needle in the Hay. Move on to bustling Prato, where the partner and chef Brandon McGlamery serves market-inspired Italian dishes, including house-made pastas and pizzas cooked in a wood-fired oven. He also oversees Luma on Park, a romantic spot with an open kitchen and a luscious pineapple curd on the dessert menu.
10) 9 P.M. After-Dinner Art
The culinary arts and the fine arts meet at the Alfond Inn at Rollins, a few blocks from Park Avenue. Established by Rollins College, the nonprofit inn funnels all proceeds to its scholarship programs. Contemporary art fills the ground floor of the 112-room hotel in a rotating arrangement overseen by the curators of the Cornell Fine Arts Museum. Join the locals for post-dinner drinks in admiring the art or sitting around the courtyard fires beside the bougainvillea hedges.
11) 8 A.M. Wild and Scenic Splash
The freshwater springs and abundant lakes of Central Florida are central to the appeal of the region. Rarely do you see such bodies of water buffered by native hardwood forests, which makes Wekiwa Springs State Park, about 16 miles from downtown, worth the trip. Giant spreading oaks festooned in Spanish moss shade the grass and palmetto fields where wild turkeys wander. Show up early to join the regulars in swimming circular laps in the designated swimming area of the Wekiva River. Rent a canoe ($19.15 for two hours) to paddle the waterway, deemed a National Wild and Scenic River, looking for wild things, including alligators, deer and black bear.
12) Noon. To Market
Few places capture the creative energy of millennial Orlando as tastily as the four-year-old East End Market. Garden plots grow herbs and vegetables outside the building in the Audubon Park Garden District. Inside, a collection of businesses skew to culinary independents, including Skyebird Juice Bar & Experimental Kitchen, where fresh-pressed juices come in canning jars; Gideon’s Bakehouse, whose substantial cookies have a cult following; and Florida & Co., serving locally raised meats and seafood in sandwiches and small plates. Eat at the picnic tables beside the garden, then wander back through to shop the nifty potted succulents at Porch Therapy and the leather accessories made on the spot at Freehand Goods.
In the pedestrian-friendly village of Winter Park, the Alfond Inn at Rollins offers resort amenities, including a rooftop pool, a restaurant that champions Florida products, and a rotating contemporary art collection from the local Cornell Fine Arts Museum. The former utility commission headquarters has been converted into the 118-room Aloft Orlando Downtown, with the original terrazzo floors, marble walls and 10-foot floor-to-ceiling windows. It is conveniently located across the street from the Dr. Phillips Center for the Performing Arts.