Discover Downtown: Urban Sophisticates 2021 Edition

Last updated on July 28, 2021

You may be familiar with downtown Orlando as a nightlife hotspot, but it’s also filled with experiences for urban sophisticates looking for more #adulting options. Explore some of the ways you can turn up and tune into a more upscale side of downtown Orlando this summer.

Artistic and Cultured

  • CityArts is a crash course in the Orlando art scene and home to regular public programs and events like a public diary reading group, “Orlando Cringe,” and an outdoor concert series in their alleyway, The In-Between Series. 39 S. Magnolia Avenue
  • Dr. Phillips Center for the Performing Arts is Orlando’s top-tier event center and performance hall with world-class theaters and performance spaces as well as a game-changing outdoor event venue created in response to the COVID-19 pandemic, the Frontyard Festival[1] . 445 S. Magnolia Avenue
  • Haos on Church is an award-winning, novel venue featuring a strong assortment of burlesque, cabaret, and theatrical performances alongside amazing food. 123 W. Church Street
  • Mad Cow Theatre is one of Orlando’s longest-running professional theatre companies and overlooks Church Street Plaza. 54 W. Church Street [GMap]
  • SAK Comedy Lab is always different and never gets old. Wayne Brady started his improv comedy career right here before his stint on the show, Whose Line Is It Anyway? 29 S. Orange Avenue
  • SNAP! Orlando is one of Central Florida’s most-loved contemporary art organizations with a focus on modern, cutting-edge photography and they run a gallery in downtown Orlando’s South Eola neighborhood. 420 E. Church Street

Taste-full Evenings

  • The Boheme (Website) is upscale and urban sophisticate worthy with a menu that is eclectic and approachable, and the furnishings are simply gorgeous. 325 S. Orange Avenue [GMap]
  • Kres Chophouse (Website) is a modern, trendy steakhouse that serves up one of the finest dining experiences in Orlando, let alone downtown, and has won multiple awards through the years, including “Best Late-Night Dining,” “Best Orlando Restaurant,” and “Best Steakhouse.” The menu features in-house aged beef that’s hand-cut to order and some of the freshest Florida fish in the region. Service is exceptional, and it’s all located in a landmark 1930s building. 17 W. Church Street [GMap]
  • The Monroe (Facebook | Website) is one of Orlando’s most beautiful new restaurants. Located in Parramore at Creative Village and the new downtown University of Central Florida/Valencia College campus, it serves nostalgic childhood favorites in an airy, editorial interior that could easily be featured in an episode of Mad Men. 448 N. Terry Avenue [GMap]
  • Reyes Mezcaleria (Website) is one of those rare spots where the food is as delicious as the interior and y’all are just gonna eat it all up. They have a great big selection of tequilas and mezcals too. It’s the perfect place for a business meeting or after-hours get-together. 821 N. Orange Avenue [GMap]
  • The Robinson Cafe (Website) may be located in one of the oldest buildings in downtown Orlando but you’d never know it when you step inside and see the light, modern interior.  63 E. Pine Street [GMap]
  • SOCO Restaurant (Website) is all about Southern Contemporary Cuisine under the direction of award-winning Chef Greg Richie. Don’t sleep on those biscuits either. 629 E. Central Boulevard [GMap]
  • Foxtail Coffee Bar (Website) is a favorite among locals, with new storefronts popping up in every neighborhood of the city over the past few years. This little outpost in DoveCote Restaurant is the easiest way to get one of their scrumptious caramel cold brews on tap while you’re downtown. Grab a coffee and settle down at one of the tables in the expansive foyer and pretend you’re in a Roman cathedral. If you’re there in the afternoon, you might as well kick it until happy hour starts in the restaurant’s bar and order some oysters. 390 N. Orange Avenue [GMap]
  • Eola Wine Company (Website) is a friendly neighborhood wine bar near Lake Eola that specializes in light bites and charcuterie boards to share with friends. 430 E. Central Boulevard [GMap]

Glass Raisers

  • Mathers Social Gathering is a speakeasy with an immaculate aesthetic and is one of the best places in downtown Orlando to see and be seen. There is a dress code, so be sure to leave the sneakers and shorts at home. 30 S. Magnolia Avenue
  • The Wellborn is a selfie-ready oasis tucked underneath the 408 and chock full of tropical plants, tiki torches, and a nod to Orlando’s rich history - the bar is located in one of the oldest buildings in the city. 211 N. Lucerne Circle
  • Hanson’s Shoe Repair was actually just an alleyway at one point until a shoe repairman simply bricked up the front and slapped a roof on top and called it a building. Now it’s one of the coolest craft cocktail venues in town. Be sure to check their Twitter page @hansonsshoeshop for the daily password to get access or you’ll just have to stay in the main bar, Bauhaus, for the rest of the evening. Which isn’t a bad thing, we just want you to get the whole experience when you’re there. Rentals and buyouts are also available if you’d like to keep things private. 27 E. Pine Street
  • Bosendorfer Lounge within the Grand Bohemian is the swanky hotel piano bar you never knew you needed. The black, gold, and deep red interior set the scene and the jazz music in the foyer is the perfect accompaniment for your stiff martini or an unforgettable brunch, which happens every Sunday from 10 a.m. to 2 p.m. 325 S. Orange Avenue
  • Corona Cigar Company and Diamond Crown Lounge is a beautiful cigar bar and lounge in the center of the downtown, featuring a staggering selection of cigars. They also have a great leather-bound lounge that’s regularly full of executives and basketball players puffing away and drinking pricey drinks. The floor-to-ceiling windows also give you premium people-watching pleasure. 127 S. Orange Avenue
  • AC SKY BAR is located in Orlando’s newest lifestyle hotel on the 18th floor with 180-degree views of downtown Orlando’s expanding skyline. It’s one of the most popular places to have brunch in town and a great spot for business and leisure dates. Get there early to secure one of the fire pits for the happy hour sunset service. 333 S. Garland Avenue
  • Sky Lounge at Amway Center features beautiful views of the downtown Orlando skyline, and is an ideal spot to meet a group before a concert or a home game. 400 W. Church Street


  • Amway Center is a state-of-the-art venue for professional sports, concerts, and unique events. It’s home to the Orlando Solar Bears, the Orlando Magic, and the Orlando Predators. Take advantage of their premium seating options to enjoy tastefully-appointed suites with VIP bars, lounges, and private catering packages. 400 W. Church Street
  • Camping World Stadium hosts massive events all year round and has hosted performances by the likes of Beyonce and Jay-Z to the Florida Cup, and EDC Orlando. They offer climate controlled private suites that come with reserved parking spaces, theatre-style seating, personalized bar areas, and customized catering options.
  • Exploria Stadium is the home of Orlando’s Major League Soccer team, Orlando City, and offers a variety of suite options for private sports-viewing shenanigans that can accommodate 14-28 guests at a time. There are 31 available suites in the stadium, and they come with VIP parking and stadium access, catering, suite attendants, and more. 

Pamper Yourself

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