In cities like Boston, Nashville, New York and San Francisco, visiting the neighborhoods is part of the itinerary. But in Orlando, where droves of tourists head straight to the theme parks, some of the city's most-cherished enclaves go undiscovered. Carve out some time for exploring these eight personable neighborhoods and quaint small towns, each with a distinct vibe and plenty of local flavor.
The Town of Celebration is a modern take on Americana. Disney started building the self-contained neighborhood as a master planned community in 1996. Today this thoughtfully designed mini metropolis, now unaffiliated with the corporate giant, is a polished, upscale residential and commercial area with old-fashioned looking homes—big on front porches—that have modern interiors within. Market Street, the main drag, draws visitors for its indoor-outdoor restaurants with lake views. Several revered architects including Michael Graves and Philip Johnson designed signature buildings. Residents and visitors make use of Celebration’s 26 miles of walking trails and 45 parks of various sizes. A Robert Trent Jones golf course is open to the public.
Plant Street, the heart of Winter Garden, is a retail and restaurant strip created from what was long a worn-down citrus center’s downtown. Quaint, friendly and free of pretention, the welcoming enclave with brick-paved streets and faux gas lamps is timeless yet trend-forward. Children jump in splash pads and couples cavort in oversized porch swings set in the center of town--where silver-haired gentlemen sometimes play Americana tunes alfresco. Adults sup and sip wine and martinis in welcoming dining rooms, cafes and watering holes—chic, bohemian or cozy. Athletes walk, jog, bike and skate by, as Plant Street is part of the expansive West Orange Trail. A brewery and indoor locavore market, plus a weekly farmers market, offer up artisan wares and groceries.
Just north of downtown is upscale enclave Winter Park, which was the area's first resort community as wealthy northerners came down in the late 1800s to escape cold winters. Today, the area is popular for its scenic lakes, thriving arts community and shopping and dining scene. Park Avenue is the main thoroughfare that runs through downtown and is chock-full of independently owned boutiques, retail stores, sidewalk cafes and art galleries. The Morse Museum of American Art holds the most-comprehensive collection of Louis Comfort Tiffany stained glass. Winter Park is also home to Florida's oldest college, Rollins College, which sits on the beautiful shores of Lake Virginia. The college has a public dock and a free art museum open to visitors.
Many visitors have compared this lakefront community to a charming New England city. Take a walk to the Palm Island Lighthouse or peruse antique shops, art galleries and boutiques downtown. Just 30 miles of downtown Orlando, exploring this town feels a bit like going back in time, where simple pleasures like eating an ice-cream cone, admiring the seasonal flowers or just relaxing in a rocking chair on the front porch take priority.
This quiet town between Orlando and Daytona Beach is filled with charm and history. Deland boasts the first private university in Florida, Stetson University. Downtown, students, locals and visitors watch movies in the 1921 Athens Theatre, shop locally owned boutiques and dine at sidewalk cafes, amid colorful outdoor murals depicting historic scenes. Local professor and chef Hari Pulapaka, who runs Cress Restaurant, is a four-time James Beard semi-finalist for best chef in the South.
A quiet agricultural community before the theme parks came to town, modern-day Kissimmee invites visitors to experience Old Florida. Visitors drive past sprawling cattle ranches while heading to traditional airboat rides. Eco tours introduce participants to Orlando’s natural side. Zip-line and ropes-course operators add a bolt of thrill to the outdoor experience. Make time to see a classic rodeo if the timing’s right. Kissimmee’s historic city center is worth a visit for its street art, including the quirky Monument of States, an early ’40s statue with mementos from 48 of the Fifty Nifty. It’s within the spiffy 25-acre Kissimmee Lakefront Park, an open-air escape with floating docks over Lake Tohopekaliga, fishing piers, wooden and paved trails, and eco “rain gardens.” Family-oriented dinner theaters abound along Kissimmee’s main tourism thoroughfare.
Dr. Phillips/Restaurant Row
Equidistant from the Disney, Universal and SeaWorld theme parks, Dr. Phillips is the only Orlando neighborhood that draws equally from tourist corridors and residential neighborhoods. Its main drag, Sand Lake Road, has become known as Restaurant Row for its midscale and upscale restaurants, which flank the street via high-end Mediterranean-style strip centers. Boutiques, upscale grocers, and polished retailers selling goods from cigars to liqueurs beckon those looking to stock their hotel rooms or suitcases. Quiet parks dot Dr. Phillips, which was named for a citrus magnate and philanthropist. Bay Hill, a residential golf community, is home to the annual Arnold Palmer Invitational.
Ivanhoe Row/Mills 50/Loch Haven
Ivanhoe Row and Mills 50 are up-and-coming Orlando neighborhoods known for their offbeat yet attractive businesses. Ivanhoe Row was long Orlando’s antiques center; now art galleries and trendy bars fill the vintage storefronts with hipster wares and fare. It’s a short walk to Loch Haven Cultural Park’s museums and theaters. Nearby, Mills 50 is two neighborhoods in one. Artsy with an edge, it’s an LGBT-friendly enclave lined with inexpensive cafes serving flavors that span the globe. It’s also Orlando’s Asian center, packed with Vietnamese restaurants, grocery stores and acupuncture practices. Seek out Mills 50’s utility boxes, dumpsters and exterior business walls; many are painted in colorful one-of-a-kind motifs by local artists.
College Park is technically part of the city of Orlando, yet this urban commercial/residential hybrid is a closely knit community all its own. The main drag, Edgewater Drive, is a pedestrian-friendly thoroughfare with restaurants, boutiques and resale furniture emporiums. Surrounding that, 1920s-era bungalows along brick roads named for universities are home to an eclectic group of residents, most of whom shop and socialize at the now-retro 1950 Publix supermarket. Author Jack Kerouac spent time in one of the bungalows. It’s now a writer’s retreat. Away from College Park’s center, expansive homes with lake views show Orlando living at its most graceful.
By day, its high-rises bustle with office workers. After dark, the streets fill with decked-out club-hoppers. Yet downtown Orlando is packed with intriguing sub-destinations worth exploring. Orlando’s creative community shows its talent in the Downtown Arts District. Its CityArts Factory boasts several galleries, nearby arts venues rotate collections regularly, and street sculptures can be found in all kinds of locales, including the exterior of a parking garage, where “Our Journey” is worth seeking out. Lake Eola is a blue oasis. There, tourists ride paddleboats shaped like swans, locals stroll the perimeter at sunset, shoppers stock up on wholesome foodstuffs at the weekly farmers market, and groups practice yoga on the lawn en masse. Hipsters live in Thornton Park’s restored historic homes, urban professionals in its contemporary condos; both groups frequent the neighborhood’s casual restaurants, some of them headliners with noteworthy fare. Big venues draw huge crowds: the state-of-the-art sports and concert arena Amway Center and Dr. Phillips Center for the Performing Arts, and the recently renovated open-air Citrus Bowl stadium. Orlando City Soccer is scheduled to open its own stadium in 2016. Before and after downtown events, attendees gather around Church Street Station, where historic buildings with fanciful adornments mix with contemporary buildings to house food, drink and entertainment venues; the area is often open only to pedestrians.