The City of Winter Park & Park Avenue District
Throughout the Orlando area, unique neighborhoods, towns and cities offer outstanding dining, vibrant arts and culture, bespoke retailers, and outdoor adventures. The City of Winter Park is one of the best thanks in large part to the acclaimed restaurants, shopping, arts and more in the upscale Park Avenue District. If you haven’t been there yet, you owe yourself a visit — here’s why.
Discover: A Perfect Day in Winter Park
Approximately 20 minutes northeast of downtown Orlando, and not to be confused with Winter Garden to the west, Winter Park gained its name after the arrival of the South Florida Railroad in 1880. The highly rated Rollins College — Florida’s first four-year university — opened shortly thereafter, heralding the city’s refined future.
Discover: Winter Park Virtual Tour
Today, Winter Park’s epicenter is Park Avenue, a tree-lined, cobblestoned street bursting with acclaimed eateries, museums and some of the Orlando area’s best shopping. The city also has much for outdoor enthusiasts, including a robust parks system and the gorgeous Winter Park Chain of Lakes.
To really experience Winter Park, you’ll want to stick around for a few days. One of the best places to do so is The Alfond Inn. Owned by Rollins College, the recently renovated, AAA Four Diamond property boasts 112 guest rooms, a full range of amenities (including a pool) and a riveting art collection. What’s more, all of the hotel’s profits endow a scholarship program at Rollins.
Discover: Orlando's Top Hotels & Resorts
Some of Orlando's top culinary artists ply their trade in Winter Park, including James Beard-nominated Chef Brandon McGlamery. He has one of Winter Park’s MICHELIN Guide Recommended restaurants, Prato, as well as Luke’s Kitchen in nearby Maitland. They specialize in innovative Italian and classic American cuisine, respectively.
Discover: Orlando’s MICHELIN Guide Restaurants
Also nominated for James Beard Award honors, Chefs James and Julie Petrakis operate The Ravenous Pig, a seasonal gastropub that ranked as a MICHELIN Bib Gourmand eatery. You can also try the Petrakises’ fare at another MICHELIN Recommended eatery, The Polite Pig at Disney Springs®, offering shopping, dining and entertainment at Walt Disney World® Resort.
Discover: Orlando’s Top Chefs
In addition to being a One-MICHELIN-Star eatery, Soseki Modern Omakase has earned a MICHELIN Sommelier Award for Beverage Director Benjamin Coutts. Also rated as a MICHELIN Bib Gourmand is Swine & Sons, while AVA MediterrAegean, Kai Asian Street Fare and Doshi are MICHELIN Recommended.
Discover: Winter Park Dining
Other local favorites in the Park Avenue area include steaks and seafood at BoVine Steakhouse and blu on the avenue, Umi Sushi, French cuisine at Chez Vincent, New American at 310 Park South, Bosphorous Turkish Cuisine, Italian at VINIA Wine & Kitchen, and farm-to-table goodness at Boca Winter Park and The Alfond Inn’s fresh-focused Hamilton’s Kitchen.
Just a short drive from the city’s core, enjoy Spanish cuisine at Bulla Gastrobar, seafood at Reel Fish Coastal Kitchen, an authentic taste of Italy at Rocco’s Italian Grille & Bar or Bar Italia, world-class desserts at The Glass Knife, Southern cooking at The Coop and 4 Rivers Smokehouse, and choice cuts at Christner’s Prime Steak & Lobster, Fleming’s Prime Steakhouse & Wine Bar, Ruth’s Chris Steak House, and The Tap Room at Dubsdread, among many other options.
Shopaholics will adore Winter Park’s exquisite array of retailers, many of which are on and near Park Avenue. For instance, homegrown boutiques like Tuni Trendy + Chic and John Craig Clothier will have adults looking their best, while Tugboat & The Bird and Bebe’s and Liz’s will do the same for children.
Discover: Winter Park Shopping
You’ll also find outposts from nationally recognized retailers Lilly Pulitzer and J. McLaughlin. Both are part of the lineup at Shops on Park, which offers 20,000 square feet of shopping and dining on Park Avenue.
And yes, you can buy more than clothes in Winter Park. Specialty merchants include The Ancient Olive Gourmet, Bang & Olufsen Winter Park, The Farmacy, Peterbrooke Chocolatier, Williams-Sonoma and Writer’s Block Bookstore, to name a few. On Saturdays, the city offers even more unique shopping at the Winter Park Farmers’ Market.
For still more retail opportunities, make the short drive from Park Avenue to Winter Park Village. The outdoor shopping center has a host of stores and restaurants, plus one of the area's best movie theaters.
Feed your inner artist at Winter Park’s galleries and museums, including Rollins Museum of Art, which offers free admission. This facility’s collection — more than 5,700 pieces from the ancient to modern periods — is so expansive that a portion is displayed as the Alfond Collection of Contemporary Art at The Alfond Inn.
Discover: Orlando Arts, Culture & History
Nearby, you can peruse the world's most comprehensive collection of Louis Comfort Tiffany's creations at The Charles Hosmer Morse Museum of American Art. Similarly, the Albin Polasek Museum & Sculpture Gardens is devoted to the work of its titular sculptor. Or, develop your own artistic talents with a course or two at the Crealdé School of Art.
The latter is adjacent to the Hannibal Square Heritage Center, where you can learn about its namesake Hannibal Square district’s origins as an important African American community. Officially founded in 1881, Hannibal Square was the site of one of the country’s earliest Civil Rights marches in 1887 and is now one of Winter Park’s most expensive sections.
Winter Park also hosts two annual, outdoor art shows. In March, the Winter Park Sidewalk Art Festival attracts more than 200 artists to Park Avenue and adjacent Central Park, while October's Winter Park Autumn Art Festival exclusively features Florida artists. Admission to both is free.
Discover: Orlando Events
If live theater is more your thing, book a date at The Winter Park Playhouse. Just blocks from Park Avenue, the 123-seat venue is one of the few professional musical theaters in Florida. And at Casa Feliz, you can enjoy a tour of the historic home on Tuesdays and Thursdays.
The Winter Park Chain of Lakes — 12 in all — includes 2,781 acres of pristine waterways, and the Winter Park Scenic Boat Tour is a fun, relaxing way to experience it. You’ll see all manner of wildlife, not to mention multimillion-dollar mansions, during the narrated, one-hour excursions, which also go past Rollins College and Kraft Azalea Gardens.
Discover: Orlando Ecotourism
The latter is one of 11 amenity-laden public parks maintained by the city, with other standouts including Mead Botanical Garden, Lake Baldwin Park, Phelps Park and Ward Park. If seeing so much green has you aching for a tee time, don't worry: You can get your golf on at the Winter Park Golf Course, a 9-hole, public course that's on the U.S. National Registry of Historic Places.
Naturally — no pun intended — Winter Park’s lakes provide plenty of aquatic adventures beyond the Scenic Boat Tour. Look into paddleboard and kayaking rentals while you’re in the area and explore it all at your own pace.
With so much to see and do, it’s no wonder why locals adore Winter Park — and why you should make it part of your travel plans the next time you’re in Orlando.
There Is Always More to Do in Orlando
Endless adventures await in Orlando — and Visit Orlando powered by BestofOrlando.com can help you save on admission to top theme parks, attractions and experiences. Take advantage of our free planning tools to discover more ways to save money in the Theme Park Capital of the World.