The city just north of Orlando, centered on Park Avenue and Central Park, with sidewalk cafes, a gastropub whose owners were James Beard semifinalists four years running, and restaurants that have been on Park Avenue since the 1980s and 1990s.
Where 4 Rivers was born: John Rivers left a healthcare career, started with a 2004 charity cookout he called the Barbecue Ministry, and flipped the Hot Brisket Now sign on Fairbanks Avenue in 2009. Now a 16-store group, still family owned, with vegan burnt ends and a kids menu.
Catch Tars baseball in Winter Park, then walk or drive a short way for a cocktail, a bakery stop or barbecue.
Watch Tars soccer or lacrosse in the middle of the Rollins campus, then walk to Park Avenue for a meal.
The original of what it calls Central Florida's first Turkish restaurant, opened on Park Avenue in 2004 and dressed in ebru paintings, silk carpets and handmade Turkish glassware. Halal meats, never frozen, and this room is where a six-city Florida group began.
A Park Avenue breakfast room since 1980, owned by the Pertz family since 1989, with Joe Pertz still making the layer cakes and his son John running the kitchen. It started dinner service in October 2025, Wednesday through Saturday.
The restaurant of The Alfond Inn, owned by Rollins College, which sends the hotel's net income to student scholarships and hangs more than 400 works of contemporary art on its walls. Chef Antwan Ellis cooks Florida Southern with local ingredients.
See Tars basketball or volleyball at Rollins, then eat on Park Avenue, a few minutes from campus.
Owned and hosted by Michael Schwartz and Richard Pannullo since March 1993, facing Winter Park's Central Park, which explains the motto: the only thing we overlook is the park. Grandma-style meatballs and Chef Pannullo's own cheesecake.
Opened on Park Avenue in 2011 by the team behind Luma on Park, and it outlived its parent: Luma closed in 2020, Prato is still here. Window-paned doors, year-round patio seating and a long communal bar, with a 2026 Michelin recommendation.
Orlando's first dedicated cocktail bar by its own account, opened downtown in 2012 by Gene and Diana Zimmerman and moved to Winter Park after its tenth year. Best for small groups, with Saturday classes where you build three cocktails from scratch.
Named for the Depression-era glass cake knives once given away in oatmeal boxes; the family collection is on display, and chips of the glass are sprinkled through the terrazzo floor. A Winter Park favorite since 2017 with 16 first-place wins in local awards.
James and Julie Petrakis, Winter Park natives who met at the Culinary Institute of America, opened it in 2007 and brew their own beer, with a beer garden out back. Four straight years as James Beard semifinalists and a 2026 Bib Gourmand.
