Best Happy Hours in Winter Park

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Oh, happy hour! Is there anything better than getting off work and enjoying drinks with friends? We don’t think so! In fact, we love happy hour so much we’ve created a list of the best happy hours in Winter Park for you to enjoy.

Check out this curated list of the best spots to spend happy hour next time you’re in the neighborhood and feeling a little thirsty!

It’s hard to walk down Park Avenue in Winter Park and not run into people gathered around Prato, waiting to get inside. A great way to beat the crowds is to stop in for happy hour! On weekdays from 4PM-6PM, you can enjoy $8 cocktails, $5 glasses of wine, and apps for under $10! Prato has a warm, contemporary design inside, but you’re also free to enjoy happy hour al fresco all year round!

Prato features hand-crafted Italian cuisine like flatbreads and pasta, as well as a vibrant bar with an extensive wine list. With options like these, you can’t pass up the opportunity to take your coworkers here after a long day!

Happy Hour: Monday-Friday | 4PM-6PM

📍124 Park Ave. Winter Park, FL 32879

Nobody does Tex-Mex better than Dallas, so Cocina 214 is bringing the flavors of Dallas straight to Orlando! When the two Texas native owners moved to Florida, they missed authentic Tex-Mex and decided to create their own, hence the Dallas area code. Now you can enjoy high-quality enchiladas, fajitas, burritos, and more without ever stepping foot on a plane.

You can enjoy their menu on a budget with their happy hour specials, running every weekday from 4PM-6:30PM. Happy hour includes $3 cervezas, $5 house margaritas and wine, as well as snacks like the $5 cocina trio or $6 avocado bites. Salud!

Happy Hour: Monday-Friday | 4PM-6:30PM

📍151 E. Welbourne Ave. Winter Park, FL 32789

If you just can’t get enough Mexican food, Pepe’s Cantina is here to help fill that void! With locations in both Clermont and Winter Park, their happy hour specials start at 11:30AM. $4.99 margaritas and sangria for breakfast? Yes, please!

Pepe’s Cantina also offers weekday specials like margarita Mondays, taco Tuesdays, pitchers Wednesdays, Teremana’s Thursdays, fancy Fridays, sangria Saturdays, and bottomless mimosa brunch Sunday. There’s something for everyone, every day at Pepe’s Cantina Winter Park.

Happy Hour: Monday-Friday | 11:30AM-6PM

📍433 W. New England Ave. Winter Park, 32789

The Ravenous Pig is a new and exciting gastropub and brewery located on Fairbanks Ave. in Winter Park. Not only do they have an amazing restaurant indoors serving up great dishes (like the mahi sandwich, goat cheese tortellini, shrimp and grits, and pastrami brisket), but they’ve also opened their doors to include a brand new beer garden!

Happy hour in the beer garden is from 4PM-6PM Tuesdays-Fridays and includes $4 beers, $6 wines, and $2 off all cocktails! Enjoy small-batch craft beers brewed right on-site, and enjoy them while playing lawn games in their gorgeous outdoor space.

Happy Hour: Tuesday-Friday | 4PM-6PM

📍565 W. Fairbanks Ave. Winter Park, FL 32789

Grab your happy hour crew and head to Boca Winter Park for some gorgeous and delicious drinks after a day of window shopping. Boca Winter Park offers a happy hour on weekdays from 3PM-6PM, because sometimes you just need an afternoon cocktail. Happy Hour includes $5 house cocktails, 1/2 off wines by the glass, and $5 featured apps for you to snack on. 

Boca also has girls-night-out specials on Thursdays starting at 3PM for $5 tastings, cocktails, and $3 wines. Be sure to keep an eye out for their special tasting events with chocolate, wine, and cheese on select nights. 

Happy Hour: Monday-Friday | 3PM-6PM

📍358 N. Park Ave. Winter Park, FL 32789

Happy hour, but make it oysters. Blu on the Avenue is located on Park Ave. and is here to serve you happy hour specials including $5 Yuengling, wells cocktails, and Three Olives Vodka. Add in $6 select wines and Old Fashioneds, as well as $12 for a dozen oysters, and you’ve got a bevy of cheap options.

Blu on the Avenue is one of the only places in Winter Park that offers a happy hour on the weekends, as well as a late-night happy hour starting at 11PM. Now you can have a go-to place for great drinks at a great price any time throughout the week!

Happy Hour:
Monday-Friday | 4PM-7PM
Saturday-Sunday | 11AM-4PM
Every day | 11PM-Close

📍326 S. Park Ave. Winter Park, FL 32789

There are three different 310 Restaurant locations around Orlando, with the original being in Winter Park at, you guessed it, 310 Park Ave. With amazing American cuisine with modern flair, it’s no wonder this restaurant has people coming back for more.

Happy hour includes $4 domestic beer, $5 premium wells drinks or Three Olives Vodka, and $6 Tito’s, Gentleman Jack, sangria, and house wine. While you’re there, be sure to check out their dinner or brunch menus with options like blackened mahi mahi, crispy duck, mushroom ravioli, or the tenderloin eggs benedict. I’m hungry just typing it!

Happy Hour:
Monday-Friday | 4PM-7PM
Saturday-Sunday | 11AM-4PM
Every day | 11PM-Close

📍310 S. Park Ave. Winter Park, FL 32789

Dexter’s is back and better than ever with the New Standard in Winter Park. Located on Orange Avenue, The New Standard is here and ready to have you coming back again and again. It’s easy to enjoy a restaurant when they offer such great happy hour specials!

Their happy hour deals includes small plates (like croquettes, wings, and burgers) and drinks specials (like $5 spritzers, margaritas, mules, beer, sangria, and wines.) The New Standard also has live music and entertainment, so there’s sure to be a show while you drink and dine!

Happy Hour:
Tuesday-Friday | 4PM-6PM

📍1035 N. Orlando Ave. Ste 101 Winter Park, FL 32789

Ready to Explore the Best Happy Hours in Winter Park? Follow our Instagram for More!

Why limit being happy to just one hour? Enjoy our list of happy hours in Winter Park, and tag us @StuffToDoInOrlando next time you’re enjoying a drink at one of the listed locations!