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 â" with its sophisticated decor and warm elegance â" could easily manage this feat without the cache of a location inside Grand Bohemian Hotel Orlando.
Get ready for a time warp to Hawaiian and South Seas kitsch (and that's before you even sample the powerful punch of their rum cocktails)! Aku Aku brings tiki culture front and center in downtown Orlando with art and decor that hearkens back to its heyday of the 1940s and '50s. Potent rum punches served in delightfully themed glasses, tiki heads, coconuts and the like, might even make the drinks taste better. Not that they need any help. Festive is the order of the evening here. Bring friends for a fun night out, pull a date into one of the cozier nooks and share bowl-sized cocktails. In here, every night feels like you're on vacation.
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 Shoe Repair is a modern-day speakeasy in a romantic upstairs enclave on Pine Street. Call a number and they'll text you a password if they've got space. Hanson's serves an array of Prohibition-era-inspired cocktails with a focus on quality bourbon. They do a mean champagne cocktail, as well.
Mathers Social Gathering's story, or at least that of the charming building in which it is housed, begins back in the 1800s, and the third-floor space that Mathers occupies is rife with charm and atmosphere. Expertly mixed craft cocktails await its well appointed customers. There are many places for cheap beer and its oft inexperienced consumers in downtown Orlando. Mathers Social Gathering is not one of them. This is a space for sophisticated winding down, whether a date night, day-washing drinks with colleagues or deal-making drinks with clients. Cocktails here are phenomenal, but they will run you upwards of $12 each. That's why if you want to experience Mathers' good-life vibe with less impact on the wallet, you should advantage of its Happy Hour, when a select list of drinks are just $7 and light bites are half off. It runs Wednesday - Saturday from 4-7 p.m.
This upscale rooftop lounge is chic without being pretentious and offers patrons lovely views of downtown from its "Ivanhood" location, steps from not only a host of other bars and bistros, but just upstairs from a sister establishment, M or (Majors) Bar. A cool venue in its own right, 60 classic cars are on display, vintage video games and pool tables beckon - and you can amble down from the roof to check it out, drink in hand, before returning to your lofty perch up top. Beautiful spot for happy hour with friends or an intimate date-night cocktail to start of end a romantic evening.
Step back in time inside the Courtesy, a downtown haunt that hearkens back to the era of Prohibition. Lovingly hand-crafted cocktails are the norm, from classics like the daiquiri and Manhattan to new spins on the old-fashioned. Events and specials abound and Happy Hour â" Monday through Friday from 5 to a very generous 8 p.m. â" features a homespun craft punch that goes for $4 a glass until it runs out. The mixologists here are no joke, oft called-upon to craft liquid creations for the highest of high-end foodie dinners and events. Pop in and test out their skills. You may sign up for a class.
So you want to go out drinking, but you're with a varied group. Some are all about the beer, others are hoping to catch some live music, and all of them are hungry. Sanford Brewing could be your love match tonight. With an array of house-brewed beers, an expanded menu of other local craft pours and a menu that features solid grub like Thai chicken wings, massive deep-fried pretzels and mac-and-cheese you can customize - not to mention indoor and al fresco seating, SBC has wide appeal. Add to that dog- and family-friendliness and al fresco seating options on scenic Sanford Ave. and you may never drink anywhere else.
With wide-open digs in Audubon Park, Redlight Redlight is the bar of choice for many of Orlando's craftiest craft brew aficionados and already has 10 years under its belt. Its ridiculously ample beer list might feel overwhelming to some, but staffers are always happy to help. Belly up and order your favorite or sample, sample, sample. With more than 250 bottles, a massive list of rotating drafts and two beer engines for cask-conditioned ales, it's like you died and went to hop heaven. Regular events, from Orlando City soccer watch parties to expert-led food pairings, level up the always casual and often educational experience.
Located in a beautiful old space in walkable, wonderful downtown Sanford, Bitters & Brass is a haven for cocktail enthusiasts. Its vast menu is sectioned off by booze: gin, rum, vodka, scotch, bourbon/rye, brandy, tequila/mezcal and more. Even absinthe gets its own section, and in their moody, dark-paneled space, with its vintage vibe, the Green Fairy is actually an excellent choice. And if you feel like spinnning Fortuna's wheel, do. Because the barkeeps here are wonderful at gleaning your preference and mood and creating something you'll be delighted to sip.
Located amid Orange Avenue's 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. What's more, the Imperial's full menu provides excellent pairings for hungry patrons. And let's face it: If 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.