Winter Park & Park Avenue District

The City of Winter Park is one of Central Florida’s most visited communities in large part to the award-winning restaurants, sidewalk shopping, acclaimed arts and more in the upscale Park Avenue District. 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 will 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. Furthermore, the hotel’s profits endow a scholarship program at Rollins.

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 Recommended restaurants, Prato, as well as Luke’s Kitchen in nearby Maitland. They specialize in innovative Italian and classic American cuisine, respectively.

Just off of Park Avenue, the MICHELIN Recommended ÔMO by Jônt is a 2025 James Beard Award finalist for Best New Restaurant. It is a sister restaurant to the Two-MICHELIN-Star Jônt in Washington, D.C.

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.

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.

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, 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, world-class desserts at The Glass Knife, Southern cooking at 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.

You will 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, The Farmacy, Rifle Paper Co., Bang & Olufsen Winter Park, 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 6,000 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.

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.

If live theater is more your thing, book a date at The Winter Park Playhouse — one of the few professional musical theaters in Florida. And at Casa Feliz, you can enjoy the live Music at the Casa series on select nights. Alternately, take a tour of the historic home on Tuesdays, Wednesdays and Thursdays.
 

In addition to numerous holiday events, Winter Park hosts two annual, high-profile 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.