Winter Park Village is full of spots for a fun and tasty date night. Take your pick from a huge selection of food and drink specials in Winter Park Village, where more than thirteen different bars and restaurants stand ready to please your palate while going easy on your wallet. We're sharing the best Happy Hour deals in Winter Park Village, plus other date ideas since this iconic Central Florida venue is newly revamped!

Want more happy hour info? Check out our Guide to Orlando Happy Hours.

Winter Park Village Happy Hour

Bar Louie

What: All 16 oz. drafts are $4-$5, select premium liquor and all wines by the glass are $6, all signature martinis and select house cocktails are $7.50, and 50% off Select Bar Bites and All Flatbreads.

When: Monday through Friday, 4pm – 7pm
Where: 460 Orlando Ave., #122, Winter Park; 407-794-9500;

Bar Italia

What: Select bar bites from $7 to $10 (including Burrata Tomato Salad and Beef Carpaccio), select pizzas are $11, select cocktails and wine by the glass are $8 (including Limoncello Margarita), and $2 off All Draft Birra & High Noon Hard Seltzer.

When: Monday through Friday, 3pm – 6pm
Where: 480 Orlando Ave C-108, Winter Park; 407-734-2290;

Image of glass of wine, a beer, and food at Bar Italian Happy Hour
Prosciutto and Riccata at Bar Italia Winter Park Village – Image by Dani Meyering

The Cheesecake Factory

What: Appetizers, small plates, and snacks (including Ahi Tartare, Chicken Pot Stickers and the Happy Hour Burger) from $8.50 – $9.95 plus specialty cocktails, such as a Mojito and a Cosmopolitan, priced at $8.50 each. Select well drinks and wines by the glass are $8.50; draft beers are $495. View the entire happy hour menu.

When: Monday – Friday from 4pm – 6pm in the bar area.
Where: 520 N Orlando Ave, Winter Park; 407-644-4220;

cheesecake factory winter park village

The Hangry Bison

What: Provisions include a selection of $5 small plates alongside eight drink options ranging in price from $5-$6. 

When: Monday – Friday from 3-6pm.
Where: 480 Orlando Ave. #130, Winter Park; 407-677-5000;

Happy Hour Test Drive: The Hangry Bison

P.F. Changs China Bistro

What: Lucky Eight Happy Hour – select appetizers, dim sum, and cocktails are $8 each.

When: Monday through Friday, 3pm – 6pm.
Where: 436 N Orlando Ave, Winter Park; 407-622-0188;

pf changs food collage

Ruth’s Chris Steak House

What: Sizzle, Swizzle, Swirl Happy Hour includes mouthwatering sandwiches and full-size appetizers as well as hand-crafted cocktails and wine starting at only $9. Indulge in Ruth’s Cheeseburger & hand-cut fries or succulent Spicy Shrimp, and perfectly pair it with a Rocks Rita.

When: Monday-Friday and Sunday from 4-6pm.
Where: 480 N Orlando Ave, Suite 100, Winter Park; 407-622-2444;

Ruth's Chris Steak House Orlando happy hour drink
Ruth's Manhattan

Sakari Sushi

What: Appetizers (included Spicy Calamari) priced from $4.25 – $5.50, plus 2-for-1 drink specials on select sakes, house wines and beers.

When: Daily from 3-6pm
Where: 510 N Orlando Ave #104, Winter Park; 407-644-5050;

Tommy Bahama Marlin Bar

What: This new tropical-inspired gathering spot is small, but welcoming, with lots of outdoor seating, and attached to a Tommy Bahama retail shop. Happy Hour includes $9 wines, $11 cocktails, $13 martinis

Happy Hour Margarita and Coconut Shrimp Tommy Bahama Marlin Bar Winter Park
Happy Hour Margarita and Coconut Shrimp – image by Dani Meyering

When: Island Time/Happy Hour will be 3-6pm daily. There will be live music 4pm-8pm weekdays and 11am-3pm on Saturday and Sunday.
Where: 438 N. Orlando Ave. Winter Park, FL 32789; (689) 345-7935;

New Winter Park Village Date Ideas

Flutes Champagne Bar

480 N Orlando Ave, Suite 133, Winter Park

Flutes is perfect for date night! This new bar in Orlando opened on December 1, 2023. The menu focuses on champagne, sparkling wine, as well as distinctive wine, and a few craft beer selections. The atmosphere is very nouveau Winter Park, a modern lounge with multiple homages to the glamourous days of Hollywood past.

Looking for a way to elevate your champagne experience at Flûtes Champagne Bar? Pair their exquisite selection of Champagnes with the finest chocolates in town from AJ Chocolate House, a European fine chocolate artisan, crafts handmade chocolates rooted in Belgian traditions. Indulge in sweet bliss with over 150 different types of sweets in a charming, retro-style setting.

Image of man playing the saxophone at Flutes Champagne Bar
Flutes Champagne Bar Winter Park – Image by Dani Meyering

Jeni's Splendid Ice Creams

510 N Orlando Ave #102, Winter Park

Jeni's is the original artisan ice cream company known best for creative flavors you won’t find anywhere else (like Brambleberry Crisp and Gooey Butter Cake). They build every flavor completely from scratch using a unique recipe that’s been honed and perfected over more than 20 years.

Their ice creams are made to be paired, which is why they offer half scoops, so you can mix and match (and never have to choose just one flavor). Pick a couple of flavors to try out with your date.

Right now, they are offering Splendid Hour! Enjoy 20% off any L’affogato every day before 5 p.m. Limited time only.

Image of a cup of ice cream with two spoons in front of a Jeni's Orlando poster
Jeni's Splendid Ice Creams – Image by Dani Meyering

Chayote Barrio Kitchen

480 Orlando Ave C-134, Winter Park

At Chayote Barrio Kitchen, they’re writing a new narrative about Latin cuisine. They call it Nueva Mesa Latina, the “New Latin Table.” This new vision celebrates the heritage and culinary footprint of all Hispanic cultures and drives LatinX cuisine to its next stage, blending both traditional and current flavor trends into a whole new genre.

At Chayote Barrio Kitchen’s bar, artisan cocktails and a taste of Latin adventure await you. In addition to outstanding cocktails, they boast a catered wine list designed to complement the bold, Latin-forward dishes from their kitchen.