Toasting Orlando's Best Dens of the Drink

Photo courtesy of A.D. Thompson
By A.D. Thompson, Orlando Local Expert

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 friends? Do you want to dress to impress, relax in your favorite, old T-shirt or don your best mouse ears? Are you leaning toward a crisp, craft-brewed cider, a peppery Cabernet with notes of vanilla or a cutting-edge craft cocktail flavored with house-made syrup? And of course, if you're planning on pairing drinks with eats or perhaps live music, that might figure into the mix, as well. Just a few questions make the possibilities seem infinite. We whittled 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 and even theme-park offerings in the form of Jock Lindsey's Hangar Bar, with Indiana Jones-themed drinks and memorabilia that pair beautifully with a waterfront setting. Belly up, friends, and prepare to sample some of the city's very  best.

9. Wally's Mills Ave. Liquors
Photo courtesy of Wally's

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.

8. Bosendorfer Lounge
Photo courtesy of Grand Bohemian Hotel Orlando

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.

7. Aku Aku Tiki Bar
Photo courtesy of Aku Aku

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.

6. The Guesthouse
Photo courtesy of The Guesthouse

A newish kid on the block in Mills 50, the Guesthouse is lush with greenery, cool and classy. The plants and lighting are just about as therapeutic and relaxing as the cocktails and it can feel a bit like you're lounging in your well-off friend's expansive pool house. Some of the city's finer food trucks make regular stops here, as well, so you'll have some quality eats to sop up creative cocktails like the bubbly Humming Bird, made with Prosecco, or the zingy Anejo Highball with its ginger beer. Classics like the Old Fashioned or a nice Gin Fizz are always winners if you're not feeling experimental.

5. Hanson's Shoe Repair
Photo courtesy of Hanson's Shoe Repair

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.

4. Mathers Social Gathering
Photo courtesy of Mathers Social Gathering

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.

3. The Courtesy
Photo courtesy of The Courtesy

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 – Monday through Friday from 5 to a very generous 8 p.m. – 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.

2. Redlight Redlight Beer Parlour
Photo courtesy of A.D. Thompson

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.

1. The Imperial at Washburn Imports (Orlando)
Photo courtesy of The Imperial at Washburn Imports - Orlando

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.