10 Best Orlando Bars: Unexpected Surprises

Ask 10 people for their idea of a great bar and odds are decent you'll get 10 different answers. Maybe more. Especially if you add the mood of the moment into the mix. Is this a first date or a night out with the girls or boys? Do you want to play dress-up or relax in your favorite, old T-shirt and broken-in flip flops? Are you feeling like a crisp, craft-brewed cider or a peppery Cabernet with notes of vanilla? More inclined to sample a fruity designer martini or a civilized sip on a 25-year, single-malt scotch? Are you planning on grabbing dinner while you're out? Is live music on your agenda? Just a few questions make the possibilities seem infinite. We're here to whittle the Orlando options down for you with a "bar salad" of sorts, a sampling of top haunts comprised of venerable old dives a la Wally's, chic hotel jazz lounges like the Grand Bohemian Orlando's Bosendorfer Lounge, intimate downtown speakeasies like Hanson's Shoe Repair -- a relative new kid on the block -- and even theme-park offerings in the form of EPCOT's La Cava del Tequila, with a roster of agave nectar that could put any Mexican fine-dining venue to shame.

10 Cask & Larder
Alright, maybe this Southern public house, the second venue for the owners of Winter Park's beloved Ravenous Pig gastropub just up the road on Orange Avenue, is known as a restaurant first, but it's playful craft cocktail menu and impressive array of house brews, not to mention beautiful, comfortable bar (with a window into the gleaming beerworks), says "welcome to happy hour" without even mentioning their salty and succulent country ham sampler. (Insert that noise Homer Simpson makes here.) If you're a foodie, or just play one on the Internet, the bar at Cask & Larder may well be the lounge you've been longing for. ((321) 280-4200)

9 The Velvet Bar
Party like a rock star at the Velvet Bar, where the Hard Rock's ubiquitous memorabilia makes for great conversation starters and a daily happy hour from 5 - 7 p.m. doesn't hurt, either. Sink into sumptuous zebra-print upholstery or grab a chair on the veranda for people watching as you overlook the resort pool. This is living. It's near-monthly Velvet Sessions event, billed as "Orlando's only rock n' roll cocktail party," would be worth the online price -- usually $29 (it's more expensive at the door) if only for the free specialty cocktails -- each event is themed -- and finger food from 6:30 - 8:30 p.m. On top of all that, you get a rock show. Gen-X'ers take note: it's usually a blast from your 80s/90s past. ((407) 503-2401)

8 Oblivion Taproom
For a pub with excessive emphasis on beer -- and by excessive emphasis I mean 40 rotating taps and the largest cider selection in town, not to mention all the bottles of ales and Lambics and sours (oh, my!) -- what sets Oblivion apart from the craft-beer-driven crowd is its secondary emphasis: the food. While much sounds like what you'd expect -- burgers, wings and the like -- Oblivion's menu is creative, with some surprising elements. Crispy pork belly, for example, or its utter opposite, seitan, tossed in the sauce of your choosing. Or the aptly named "Fatass" burger, topped with Italian sausage, bacon, chopped pork, Tasso ham, chicarrones, pickles, jalapenos, fried onions and smoked bleu cheese, with two fried eggs and "whiz" on a grilled garlic bun. Come to think of it, maybe you should go for a light beer.... ((407) 802-4800)

7 Bosendorfer Lounge
What's black and gold and red all over? If you're in downtown Orlando and don't know the answer, the joke is on you, because you're missing out on the Bosendorfer Lounge, one of the city's sultriest locales for cool martinis and even cooler live jazz and soul. Five-star hotel bars are generally imbued with a high level of sexiness, if for nothing other than their proximity to crisp, expensive high-thread-count sheets, but the Bösendorfer Lounge -- with its sophisticated decor and warm elegance -- could easily manage this feat without the cache of a location inside Grand Bohemian Hotel Orlando. ((407) 313-9000)

6 Wally's Mills Ave. Liquors
Some people call it a dive. Or a hole in the wall. But Wally's considers itself a tried-and-true neighborhood bar that's steeped in tradition. Whatever your classification, it's an undeniable institution that's been pickling the livers of Orlando's thirsty residents since 1954. Though worn and weary it may appear, its varied clientele -- on any given day your de facto drinking buds might be 25 or 65 or both -- are most often warm and welcoming. Moreover, its worldly barkeeps are renown for pouring the stiffest drinks in town. (407-896-6975)

5 La Cava del Tequila
For reasons that may or may not be more convincing to those among you who are parents, I have long held that bars at theme parks are a brilliant idea. This one, however, housed in the Mexico Pavilion at EPCOT, qualifies as a true oasis, particularly during Orlando's hottest months. A small selection of Mexican apps is available to pair with a surprisingly creative array of margaritas and more than 100 varieties of tequila in a cozy (read: it's on the small side) enclave made friendly by cast members and even friendlier for the nectar they serve. ((407) 842-1132)

This is the stuff of Gen-X fantasy: Craft brews and video games in one cozy place. Oh, and art. Which classes the place up amid the comforting pings and memorable jingles of arcade classics like Donkey Kong and Space Invaders. Of course, art and IPAs weren't something we considered while waiting to play the lone Ms. Pac-Man game at the roller rink in 1982 (or toughing out our addictions with inferior Atari graphics in the musty confines of our parents semi-finished basements). But we're all grown up now. Things have like, totally changed. ((407) 796-2522)

3 Hanson's Shoe Repair
A classy newcomer to Orlando's downtown bar scene, Hanson's Shoe Repair is generating some well deserved buzz in a tiny upstairs enclave of the NV Bar on Pine Street. With room for perhaps 30 patrons at a time in its cozy and beautifully restored nook -- which boasts a lovely enclosed patch of rooftop for outdoor imbibing, occasional live music and (va-va-voom) burlesque -- it's a space that back in the late 1800s was, in fact, an actual cobbler's shop. These days, Hanson's is a modern-day speakeasy -- call a number and they'll text you a password if they've got space -- serving an array of Prohibition-era-inspired cocktails with a focus on quality bourbon. They do a mean champagne cocktail, as well. ((407) 476-9446)

2 Redlight Redlight Beer Parlour
Now settled into its wide-open digs in Audubon Park, Redlight Redlight remains a favorite of Orlando's craftiest craft brew aficionados, but fear not the bearded hordes (though you will encounter many as this is their natural habitat), just belly up and order your favorite or sample, sample, sample. With more than 250 bottles -- including vintage selections -- 23 rotating drafts and two beer engines for cask-conditioned ales, it's like you died and went to hop heaven. Get one of their "passports" and drink your way to an honorary Ph.D. (407-893-9832)

1 The Imperial at Washburn Imports (Orlando)
Located amid Orange Avenue's burgeoning "hip strip" of Ivanhoe Village, the Imperial Wine Bar & Beer Garden should really be on everyone's list. Why? If you've ever pondered the potential joys of having a bar inside your favorite store, you won't ask. This unique haunt, nestled inside Washburn Imports (a phenomenal home furnishings showcase with pieces from the far-flung corners of the world) seems decorated for Bacchus himself. And yes, everything is for sale. Pull up a stool fashioned from centuries-old railroad ties or some such thing and enjoy the wine and microbrews. With a new chef on board, the Imperial's full menu provides excellent pairings for hungry patrons. And let's face it: Ii you're going take anything home against your better judgment while under the influence, it may as well be a gorgeous $1,500 reclaimed-wood bookcase. ((407) 228-4992)

A.D. Thompson has spent more than 20 years as a professional writer and roughly 15 as a Floridian. The words, she has found, come easier with bare feet and rum. A roller coaster enthusiast, A.D. readily admits there is fun to be had amid the madness of the theme parks, but has found there is magic, as well, in the outer-lying reaches of Mickey’s long shadow. She is delighted to share with you the spoils of her adopted city. Visit her colorful compendium at www.amydrewthompson.com.  

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Maps and Directions

Cask & Larder 10Best List Arrow
Type: Bar, Brew Pub
Neighborhood: Winter Park
The Velvet Bar 10Best List Arrow
Type: Bar, Hotel Bar, Live Music
Neighborhood: Universal
Bosendorfer Lounge 10Best List Arrow
Type: Bar, Hotel Bar, Live Music, Lounge
Neighborhood: Downtown
Wally's Mills Ave. Liquors 10Best List Arrow
Type: Bar
Neighborhood: Colonialtown
La Cava del Tequila 10Best List Arrow
Type: Bar
Neighborhood: Epcot ®
BART 10Best List Arrow
Type: Bar
Neighborhood: Colonialtown
Hanson's Shoe Repair 10Best List Arrow
Type: Bar, Live Music, Lounge, Nightlife District
Neighborhood: Downtown
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