Cask and Larder565 W. Fairbanks Ave., 321-280-4200; caskandlarder.com
This "Southern Public House" has already reached legendary status. Occupying a landmark building, James and Julie Petrakis' latest venture serves terrific nouveau-Southern fare as well as brews made in-house. It has also become known for its creative craft-cocktail menu, which changes regularly. Think brown butter-infused bourbon old-fashioneds and an Earl Grey tea and sage-vodka lemonade.
The Courtesy Bar114 N. Orange Ave., 407-450-2041; thecourtesybar.com
Gene Zimmerman, owner of downtown Orlando's Courtesy Bar, says he sources the best herbs, spices and ingredients around town and collaborates with chef Kevin Fonzo of K Restaurant to concoct imaginative mixers (like cherry-tarragon soda) and garnishes (like smoked manzanilla olives). Big points for the bar's retro-cozy and sophisticated decor – a nice respite from some of its louder, rowdier neighbors on Orange Avenue.
Hanson's Shoe Repair27 E. Pine St., 407-476-9446; facebook.com/hansonsshoerepair
The new trend in downtown Orlando these days seems to be that of "mixology" hangouts with retro flair. The Speakeasy at Hanson's Shoe Repair re-creates the Depression-era secret stiff-cocktail culture (they do not allow cellphones in here) and offers you a chance to enjoy a (sorta pricey) Negroni, martini or French 75 out on a lovely balcony. You'll have to call in advance, though, as you need a password for entry.
1036 N. Mills Ave.; willspub.org
For the most part, you can expect to go in there, slide into a booth and order your drinks in an environment where you're not necessarily screaming over the band to have a conversation with your drinking buddies. But, on select nights, the bar becomes a venue for smaller-scale shows – like string bands or jazz trios – and intimate dance parties. In addition to craft beer and wine, Lil Indies now features a creative menu of craft cocktails (like the Indie Rock, house-made rock and rye with cacao and cherries), which changes regularly.
The Matador724 Virginia Drive; facebook.com/thematadorbarorlando
Once a favorite downtown haunt, Matador has relocated and now calls the ever-burgeoning Mills 50 district home. The Matador is a little less buttoned-up than other craft-cocktail places in town, making it a favorite with ginhounds and beer drinkers alike, and the outdoor patio, which faces Virginia Drive, is usually packed with people.
The Pharmacy8060 Via Dellagio Way, 407-985-2972; thepharmacyorlando.com
A pharmacy-themed speakeasy located right next door to the Table. Find the secret elevator door to get into the bar, which is decked out with vintage decor and stocked with bottles of liquor from craft distilleries around the region.
124 N. Park Ave., Winter Park, 407-262-0050; prato-wp.com
You'll battle crowds to get a seat at this Park Avenue It Spot, but once inside, the rustic Italian food and young, thirsty crowd will justify the body-checking. Don't leave without sampling an Italian Citrus cocktail.
The TreehouseMagnolia Avenue, downtown Orlando, 407-205-2062; facebook.com/thetreehouseorlando
You'll know you're in the right place when you see the "turf floor, green door." There's no sign for this treehouse-themed speakeasy, so you need to know where you're headed in order to find it (look for the green door between Frank & Steins and Pine Street). Once you're inside this cozy space, treat yourself to specialty cocktails like a basil lemonade or a cucumber gimlet.
The Woods49 N. Orange Ave., 407-203-1114; thewoodsorlando.com
This rustic second-floor craft-cocktail bar supports small-batch distilleries and craft breweries. Stop in for a drink or sign up for a cocktail class to learn tricks of the trade from the Woods' top-notch bartenders.