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 working environment, Austin's provides a steady infusion of both. Add to this local art for sale on its walls, a better-than-decent collection of tabletop games and amusements and a very nice craft beer menu. Add to THAT an eclectic and affable staff, a solid menu that runs from carnivorous to dedicated vegan and live entertainment – open mic, poetry, jazz, hip-hop – and all kinds of evening events. Now we've really got something, don't we? Don't come here expecting fancy. It's not. Friendly, however, they have in spades. And if you want a good panini at 3 am, you can have that, too.

Recommended for Winter Park's Best Nightlife because: Looking for a venue where you can turn day life into nightlife or vice-versa without going home to change? Try Austin's!

A.D.'s expert tip: Five words: mile-high peanut butter pie. Don't say we didn't warn you.

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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 away!), live music on Tuesdays, rotating craft beer specials, half-off burger days, a killer brunch and other tempting promos and events, the Porch is one of those places that could skew restaurant one day, bar another â€" just depends on your intent. DJs one night, karaoke the next and always, all kinds of cheese draped, bacon-wrapped, gravy-soaked goodness coming out of the kitchen.

Recommended for Winter Park's Best Nightlife because: The Porch is reliable fun for nights out watching the game, with an impressive bar and food menu to make camping out extra delicious.

A.D.'s expert tip: Drink specials run for the duration of every Orlando City soccer match.

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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 also share kitchens. Hence, much of the food is Vincent-prepared and the brunch menus, in fact, are identical. Commonalities aside, Hannibal's on the Square is sleek and hip and appropriately mood-lit with small plates, craft cocktails and wonderful (but meal unintrustive) live music. It's a nice option for intimate date nights and larger, group outings, as well. Small plates are ideal for sharing a nibble between sips.

Recommended for Winter Park's Best Nightlife because: Date night, group night, but Hannibal's won't be a too-late night. It's an elegant venue, ideal for small plates and posh sips.

A.D.'s expert tip: Sophisticated and understated, Hannibal's boasts a beautiful location that makes it nice for your whole night out, or just a start to your evening.

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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 cocktail â€" with the added bonus of being able to order one of Prato's wonderful pizzas or a side of meatballs to go with your beverages. Exposed brick, twinkly lights and some patio seating on Park Avenue give the place a cosmopolitan feel. And if the weather's right, sip al fresco and enjoy good company in its classy-but-casual environs.

Recommended for Winter Park's Best Nightlife because: Did we mention the Cetriolo? Seriously, though, the spacious square bar at Prato makes a wonderful atmosphere for date-nightlife or plain, old hang-with-your-friends fun.

A.D.'s expert tip: The Cetriolo cocktail, a refreshing amalgam of cucumber-infused vodka, lime, white cranberry and basil, imbues one's happy hour with spa-like Zen.

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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 with the tradition of clandestine lairs where super heroes and villains hone their craft, come evening, a passage at the back of this unassuming store opens and lo – a vast place for gaming, drinking, dancing, trivia-ing.... Okay, not a word. But you get the point. This casual geeky haven is loads of fun, a place where comic fans can take their Marvel-D.C. debate into the wee hours over a burger and craft beer or cocktails or crown themselves king or queen of awesome, useless knowledge on trivia night. Movie nights, DJs and other entertainment abound. Or you can just hang out, play a game, read a comic. Good stuff.

Recommended for Winter Park's Best Nightlife because: Finally, a sports bar for the Megacon set: no sports! The Geek Easy is the nerds' home in Winter Park.

A.D.'s expert tip: Love to sing? Come for Nerdy Karaoke, every Friday from 8 p.m. to closing time.

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"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 food menu of light bites and entrees provides ample follow up to craft beers and/or cocktails and of course, this is the Orlando area's best movie theater, too – showing new indies and all kinds of classics. Regular events add to the festivities, but there's no need to wait for something special to pop in for an after-work beverage or date night. In fact, this listing is actually in neighboring Maitland, not Winter Park, but it's so close (and so good), we can't leave it out in good conscience!

Recommended for Winter Park's Best Nightlife because: Dinner, drinks and a movie has never been this good, we promise. In fact, Eden Bar is so great, the movie isn't even mandatory.

A.D.'s expert tip: Looking for a lunch spot? Eden Bar runs all-day Happy Hour specials (food and drink) Monday-Friday, 11-5.

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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 if the opportunity presented itself. Warm woods and exposed brick make for a chic but comfortable setting; and tasty, reasonably-priced fare to accompany your wine selection up the ante. Kale Caesar salad, goat cheese quiche, house-cured pastrami and many more mouthwatering selections are on tap along with the beer. Feeling brunchy? Pop by on Sundays for a mimosa flight. The Parkview is as good a choice for a family lunch as a Friday date night.

Recommended for Winter Park's Best Nightlife because: A nice Park Avenue alternative to the uber-fancy, the Parkview has great eats and drinks, sans pretension.

A.D.'s expert tip: All kinds of events populate this venue's calendar. Some are ticketed and sell out! Keep up with them on Facebook to stay on top of the goings-on.

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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 Bombs, corned beef and cabbage and cold pints of Guinness. It's not just another college bar, however. A regular slate of live musicians makes it a far-and-wide local favorite, as well. It's even been featured on the Food Network. There's plenty of room for socializing at the bar but ample table choices if you're looking for a quieter night out. Versatile, comfortable, hospitable: Fiddler's Green is a fine choice.

Recommended for Winter Park's Best Nightlife because: AT Fiddler's Green you'll find live music, great pours, friendly faces, Irish charm. You can't argue with that.

A.D.'s expert tip: Fancy some darts? Fiddler's Green has its own league, but you don't have to be a ringer to enjoy a few games and a pint or two.

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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 straight from the Gen-X'er's childhood to create a trendy, comfortable space that's sentimental-hip. For Millennials and under: retro-hip. Dialing into the pay phone downstairs (shades of "Get Smart") will gain you admittance to this swinging lounge where original elixirs like the Serpico and Dr. No pair with flatbreads such as Guido Sarducci. Those more beer and wine inspired will find beverages to suit, as well.

Recommended for Winter Park's Best Nightlife because: Great cocktails, friendly staffers, good music, fun decor. Park Social's only drawback is that it will make you regret selling your grandparents' furniture.

A.D.'s expert tip: Wondering what to wear? Keep it smart – collared shirts for the gents, leave your shorts and hoodies home.

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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 spend time sharing their knowledge. With a little effort, they'll guide you to an $8 cabernet that rivals the most expensive bottle in the joint. The "automat" style makes sampling fun. Put some money on their debit-like wine card, and sample as many of the 150+ bottles as you want by plugging your card into each dispenser. Great for date nights, special occasions, friendly nights out.

Recommended for Winter Park's Best Nightlife because: Wine experts and novices will enjoy playing with the notes amid the Wine Room's vast selection.

A.D.'s expert tip: Cheese and charcuterie lovers be warned, they offer flights to pair with your wine.

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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.

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