Beer Up Or Wine Down Amid Winter Park's Best Nightlife

Sure, you'll find more than a few Park Avenue locals on this Winter Park list – and why not? The posh, brick-lined streets of this lovely neighborhood are home to many a fine food-and-drink establishment. Case in point: the Wine Room. With its sleek, enomatic wine dispensers, oenophiles both amateur and expert can sample bottles from around the world at their leisure as they relax in warm, comfortable confines with a cheese board. Not your thing? Perhaps you should utter the secret word at Park Social and gain admittance to a lounge with retro speakeasy chic and an army of skilled, friendly barkeeps happy to serve up something that's as kitsch-ily named as it is refreshing. In the mood to catch a game? Even if you didn't plan on eating, you should probably visit the Porch with an empty stomach. It's menu is way too tempting to pass on completely. And if a truly sophisticated and elegant evening is what's called for, Hannibal's on the Square may well suit. Shall we play a game? (How about Global Thermonuclear War?) If you got that WarGames reference, you may feel comfortable at the Geek Easy, a deftly disguised bar at the back of A Comic Shop, where devotees of the d20 (and other realms of fandom) get their trivia, karaoke and movie nights on in the company of their fellow geeks. 



Austin's is open 24 hours, so if you like to party where you keep your off-site office, you're in luck. Hyperlocal and frequented by both college students and Wifi-powered freelancers with a need for excellent Fair Trade coffee and a pleasant...  Read More



Looking for a new home to catch those Orlando City games? Monday night football? A host of other sporting events? The Porch could be your sports bar love match. Casual and friendly with solid Southern American fare (seriously, dieters: stay...  Read More



Its neighbor and sister restaurant, Chez Vincent, has been pleasing the palates of Winter Park and beyond with fine French fare since 1997. Even so, many are unaware that Hannibal's and Chez Vincent share more than proprietors and walls – they...  Read More



Sure, Prato is one of Park Avenue's top venues for dining but the expert gunslingers behind its lovely and expansive bar are not to be dismissed. Theirs is a wonderful place to while away an evening with a good bottle or an expertly mixed...  Read More



We hate to use the whole "bigger on the inside," Doctor Who analogy (no, we don't), but in the case of the Geek Easy, it's literal and figurative. By day: A Comic Shop (yes, that's actually what the shop is called); by night: a bar. In keeping...  Read More



"One-of-a-kind ambiance" is phrase all-too-often tossed about. At Eden Bar, it's the real deal. Lovely and al fresco, but amply covered if the weather turns, this aptly named enclave is set amid lush foliage and towering oaks. An expansive full...  Read More



Fabulous wine and craft beer and a tantalizing food menu (Yes, actual food; not just bar bites and tapas!) make the Parkview an excellent selection when you're in the mood for a comfortable drinking venue, but wouldn't say no to lunch or dinner...  Read More



You don't even have to walk into Fiddler's Green to get a sense of its cheery Irish spirit. Walking distance from Rollins College and close to the multitude of dining and nightlife options on Park Ave., this venerable pub is known for its Car...  Read More



Melding '70s style with Prohibition-era surreptitiousness, Winter Park's Park Social is an amalgam of kitsch and posh, serving craft cocktails and bar bites with era-relevant pop culture names. Same goes for its decor, which culls pieces...  Read More



The Tuscan-styled Wine Room makes use of a system of self-serve, portion-controlled Enomatic wine dispensers to facilitate service. And seriously? It's fantastic. Staffers here are not only passionate about wines, they are more than happy to...  Read More


Meet A.D. Thompson

Amy Drew has spent nearly three decades as a professional writer and roughly half her life as a Floridian. The words, she has found, come easier with bare feet and rum.

A roller coaster...  More About A.D.