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A Look at the Best Bars in Winter Park, FL

Winter Park is one of Orlando’s standout neighborhoods — it’s loaded with things to do and places to shop. But most compelling to anyone who’s looking for a night on the town is the stellar selection of bars in Winter Park, FL, with plenty of options to suit both upscale and casual occasions. Here are a few of our favorites.

Our Favorite Winter Park Bars

  • Fiddler’s Green is a classic Irish pub, and that’s reflected in the decor, the menu, and that attitude. It’s a phenomenal place to enjoy a Guinness and a Shepherd’s pie, and so much the better if you’re able to do so with friends without the worry of choosing a designated driver.
  • Park Social is a callback to the 70s, where you’ll relax on plush couches with your friends and enjoy the ambiance amidst background music from luminaries of the age such as ABBA and Steely Dan. A classic cocktail den, Park Social also features craft beers, wines, and unique snacks such as a Chicken and Waffle Cone and a Truffled Jiffy Pop.
  • The Geek Easy is a special place for people of certain tastes — during the day, this establishment is a comic shop, but at night it transforms into a bar replete with burgers, cocktails, and trivia. While here, it’s as easy to spend time with friends as it is to enjoy comic books and a beer late into the night.
  • The Porch is a purveyor of classic American bar food, an impressive craft beer list, and cocktails, too. If you’re looking for a big burger with unfathomable layers, this is the place to visit! The standout of the menu is the Early Riser, which decks out your choice of protein patty with brie, applewood smoked bacon, caramelized onions, house bbq sauce, and fries to top it off.

Enjoy The Bars in Winter Park, FL By Letting Someone Else Drive

Signature Transportation Group boasts a fleet of vehicles to suit parties of all sizes throughout central Florida. From car service to party buses, we would be delighted to help you enjoy Winter Park’s nightlife.

Sedans and SUVs

  • Lincoln Continental
  • Mercedes-Benz S-Class
  • Cadillac Escalade
  • Chevy Suburban
  • Cadillac XTS


  • Limousine-Style Mercedes-Benz Sprinter
  • Turtle Top
  • Executive-Style Mercedes-Benz Sprinter

Executive Buses

  • 24-Passenger Executive Bus
  • 39- to 43-Passenger Executive Bus
  • 55-Passenger Motor Coach

Special Occasion Vehicles

  • 30-Passenger Trolley
  • 36-Passenger Limousine Style Party Bus

Let Signature Transportation Group Drive You

Whether you’re looking to go bar-hopping or you need to get to or from the airport, Signature Transportation Group can help. You can even book online!