Bars and Breweries
Chroma Modern Bar and Kitchen
6967 Lake Nona Blvd., Orlando, FL 32827
Chroma in Lake Nona is known for its seasonal cocktail menu and handcrafted sodas. The bar is warm and welcoming and many of the cocktails pair well with the eclectic food menu that includes sharable plates and appetizers from all kinds of cuisines (tacos, pad Thai, pasta, ribs and curry fried chicken all bump elbows on the menu). Opt for the refreshing Bottled Sunshine, which mixes lemon, orange and tangerine juices with Solerno blood orange liqueur and Reyka vodka and is served in a bottle.
Crooked Can Brewing Company
426 W. Plant St., Winter Garden, FL 34787
Hanson's Shoe Repair
Driving into Winter Garden, it’s hard to miss the Crooked Can Brewery. This local favorite is known for its free spirit, laid-back approach to beer making, excellent taste, and unmatched quality. Grab a seat inside or soak up the sunshine on their outdoor patio while sipping on their classics like the cloud chaser and the high stepper.
Hanson's Shoe Repair
27 E. Pine St., Orlando, FL 32801
Housed in another historic setting – completed in the 1880s, the building might just be the oldest in downtown Orlando – Hanson's Shoe Repair serves craft cocktails inside and outside on the patio. Be warned: You will need the daily password to enter, but it can be acquired through social media, or by calling or texting the bar. Hanson’s is very committed to its speakeasy theme, so phones and photos are not permitted. Let this be a lesson in how people had fun before iPhones existed.
Mathers Social Gathering
3 Phoenix Building, 30 S. Magnolia Ave., Orlando, FL 32801
Housed in a historic building in the heart of downtown Orlando (it's been on Magnolia Street since 1894!), Mathers Social Gathering is where dapper bartenders shake up drinks made with small-batch spirits and house-made cordials, bitters and syrups. The bar is known for Prohibition-era specialities like bathtub gin — a surprisingly creamy drink made with Brokers gin, ground lavender, honey simple syrup, lemon and half-and-half.
The Ravenous Pig Brewing Co
565 W. Fairbanks Ave., Winter Park, FL 32789
This local brewery is run by the same team that own the next-door restaurant, The Ravenous Pig. The craft beer spot has year-round staples like Lone Palm golden ale and the Working Man porter, as well as a rotating selection of seasonal and limited-edition beers. You'll also find their selections at a number of pig-themed eateries, like The Polite Pig at Disney Springs and Cask and Larder at the Orlando International Airport. If you like what you taste, purchase a growler to take home with you.
Regency Beer, Wine, Liquor
16100 Marsh Rd., Suite 201, Winter Garden, FL 34787
When you don’t feel like grabbing a seat at an everyday bar, the Regency Beer, Wine, and Liquor store is here. But it isn’t your average liquor store. Not only do they have an incredible selection of beers and wines for you to take home. They also offer in-house tastings for you to enjoy during your shopping experience.
Toll Road Brewing Company
101 W. McKey St., Ocoee, FL 34761
Want to drink like a local? Off the beaten path, just a short drive out of Winter Garden, you’ll find Toll Road Brewing Company — named after the infamous Florida toll roads. This local-favorite brewery is a small craft brewery that specializes in craft beer made in-house, as well as showcasing other local Orlando breweries.
The Attic Door
28 W. Plant St., Winter Garden, FL 34787
Whether you’re in search of the perfect date spot or a place to spend an afternoon with your crew, Winter Garden’s Attic Door should be at the top of your list. This swanky wine bar, bistro, and live music venue serves up unique wines, craft beers, and great bites.
Lakeridge Winery & Vineyards
19239 US 27 North Clermont, FL 34715
Being Florida’s largest winery, Lakeridge Winery & Vineyards is an Orlando must-visit for locals and tourists. Located in Clermont, you’ll find 127 acres of rolling hills covered in Muscadine grapes — the same grapes used to create the award-winning wines you can taste or purchase in their gift shop.
The Wine Room on Park Avenue
270 S. Park Ave., Winter Park, FL 32789
Rustic-casual venue with 100+ wines to taste via a machine dispenser, plus artisanal cheese and tapas.
Wine Bar George
1610 E. Buena Vista Drive, Lake Buena Vista, FL 32830
Wine Bar George at Disney Springs boasts a curated list of over 140 wines by the ounce, glass or bottle. Each of the servers are uber-knowledgeable and can suggest a pairing with food or make you a flight of wine based on your answers to a few simple questions. The food is just as impressive, and includes sharable plates and charcuterie boards. If you’re lucky, you’ll spot resident Master Sommelier George Miliotes, who can sometimes be seen pouring wine and greeting guests.
Dance The Night Away
There is no better place to perfect your two-step than Cowboys, the city’s Western club of choice. The off-the-beaten-path venue boasts Orlando’s largest wooden dance floor at a whopping 20,000 square feet, along with a patio and multiple bars. Bonus points: You can nab free dance lessons so you aren’t lost when the party really starts to kick up when old-school Garth Brooks or Reba McEntire are blasted through the speakers and everyone starts singing along.
The Independent Bar
A downtown staple, this unassuming three-tier hangout with two dance floors spins music as eclectic as the crowd – hip-hop, house, Motown and New Wave all hold space on the dance floor – and the reasonable prices mean you’ll still have money left over to spend on quintessential hangover-preventing fare at the nearby food trucks. It’s an unpretentious local favorite, free of velvet ropes or bad attitudes.
A nightlife staple for more than a century, The Beacham has hosted the likes of Elvis, the Ramones, Pretenders and DJ Khaled. A concert venue on most nights, the space turns into downtown's largest nightclub on the weekends, attracting a young crowd with two dance floors populated by dancers and DJs spinning mostly hip-hop and rap. If you've got the cash, opt for VIP service, which comes with a private security and servers.
Orlando’s take on a Vegas-style club, Tier attracts a good-looking crowd willing to dish out the cash for a bottle of Ace of Spades. Private skyboxes set the high rollers apart but even the more down-to-earth clubber will enjoy the view atop the balconies overlooking the dance floor, state-of-the-art lighting and five bars. While EDM reigns supreme, the Friday-themed parties always draw a crowd.