The Courtesy is a good place to start, because it is well known in Orlando. It has a killer absinthe collection and a handful of creative cocktails. Try the Piedra Almas, Mezcal, house made mango shrub, yellow Chartreuse, fresh lime, and candied lime garnish. The Courtesy offers The Courtesy Cocktail Class on the first and third Saturday of every month. This is a great way to not only sip great cocktails, but to learn to make them!
The Courtesy, 114 N Orange Ave, Orlando, FL, USA +1 407 450 2041
Hanson’s Shoe Repair
The exclusive Hanson’s Shoe Repair requires a password to get in but the cocktails are worth the trouble. You will feel like you are in the heart of the Prohibition Era in the oldest building in Orlando. If that is not cool enough for you, try the Bijou: Beefeater gin, green Chartreuse, Dolin rouge, and Angostura orange bitters. Get the daily password on the Twitter feed.
Hanson’s Shoe Repair, 27 E Pine St, Orlando, FL, USA +1 407 476 9446
The Woods is in a historic building and rotates its menu monthly. The décor makes you feel like you are in the forest. Table tops and the bar are naturally shaped pieces of trees. The Woods also caps the number of patrons that come in, so it’s never overcrowded, and you can have an actual conversation without shouting. Try the Chupacabra: Tres Agave Reposado tequila, Aperol, King’s Ginger, and grapefruit juice. If you don’t see anything on the menu that looks interesting, you can request a custom drink.
The Woods, 49 N Orange Ave, Orlando, FL, USA +1 407 203 1114
The Matador has been revamped with a dark red and black color scheme that almost shouts ‘hipster.’ Beards or not, this place has great drinks. They take a while to mix up, but they’re totally worth it. The Matador also has over 20 beers on tap. Ask for the Sunflower, a delicious blend of St. Germain, gin, absinthe, and lemon juice. Even those who don’t love gin will appreciate this drink. The billiards table is free.
Lil Indies is small. It’s almost hidden by Will’s Pub, but you will be glad you took the extra effort to find it. Lil Indies is like a dive bar but without the grunge. There isn’t much seating, so be prepared to stand. Try ordering Death in the Shade, Herbsaint Legendre, Tahitian and Merkat lime, coconut water, sugar, and mint. This drink is not at all fruity but feels very tropical. Behind the DJ booth is some hidden seating.
Lil Indies, 1036 N Mills Ave, Orlando, FL, USA +1 407 748 8256
The entrance to The Pharmacy is hidden behind a set of doors that look like elevators. There are no signs, but if you call, you will get directions. The inside is beautiful decorated, almost modern. The menu is broken down into ‘Elixirs’ for drinks and ‘Prescriptions’ for food. It has some of the most delicious food and drinks in Orlando. The Pharmacy is more of a sit down dinner spot, but the drinks are so good, it’s worth stopping in. Try the Airmail, Caña Brava rum, lime juice, Pharmacy simple syrup, and Flor Prosecco. The seating is family style, so you might get cozy with strangers.
The Pharmacy, 8060 Via Dellagio Way, Orlando, FL, USA +1 407 985 2972
Luma on Park
Luma on Park is a foodie favorite with amazing cocktails, and it is a place for tequila lovers. While known for incredible food, Luma steps up big time with great cocktails to complement the menu. Try the Tequila Pine, pineapple habañero tequila, house made vanilla simple syrup, pineapple juice, and lime. If you aren’t in the mood for sit down dinner but want to try the cocktails, there’s a lounge that offers small plates and cocktails.
Luma on Park, 290 S Park Ave, Winter Park, FL, USA +1 407 599 4111
The concept is simple: put a bar in the center of the room and have the atmosphere revolve around amazing drinks. It works. The bartenders at The Guesthouse are friendly, and happy hour goes on until 8pm. It has traditional drinks like the Moscow Mule and the Old Fashioned, but there are also some adventurous cocktails worth trying, like the Army Navy: Hayman’s Royal Dock Gin, Orgeat, Angostura lemon, and cherry.
The Guesthouse, 1321 N Mills Ave, Orlando, FL, USA +1 407 630 6574
Cask and Larder
Cask and Larder is awesome for a variety of reasons. Not only does it brew its own beer, but it also specializes in real Southern cooking; I am talking your grandma’s cooking, but taken up a notch. It has a selection of cocktails that will make your toes curl. Try the Pear Jam: Ron Barcelo Añejo rum, St. George pear brandy, sherry, and saffron bitters.
Cask and Larder, 565 W Fairbanks Ave, Winter Park, FL, USA+1 321 280 4200
The Whiskey specializes in burgers and whiskey. Not all the craft cocktails are made with whiskey, but why mess with a good thing? It’s not just the cocktails that are craft, the burgers are delicious and balance out the drinks nicely. Try the Rock a Roller, Bulleit, strawberry liquor, rhubarb bitters, and lemon juice. There is live Blues music on Tuesday.
The Whiskey, 7563 Sand Lake Rd, Orlando, FL, USA +1 407 930 6517