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4 Amazing Restaurants on Park Avenue in Winter Park

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The quaint and charming shopping street, Park Avenue, lies in the heart of Winter Park, Florida. With more than 140 unique boutiques and restaurants, Park Avenue’s most prominent features are its gorgeous oak canopies and brick streets. 

 The restaurants on Park Avenue only add to its charm. With food from all over the culinary map, it’s no wonder this is a popular date night spot. Keep reading and we’ll tell you all about the best restaurants on Park Avenue.

Fresh, farm-to-table dishes are Boca’s specialty—with only local ingredients, their menu features some of the tastiest food around. Boca’s mission is to provide fresh, local, seasonal, and sustainable food to everybody. 

Boca offers a $29 to-go deal for two that includes a rotating entree, house salad, and a dessert for each person. Available Monday through Friday, 4PM–9PM, and to-go only. Order pickup and have a relaxing date night at home!

Monday–Thursday | 5PM–10PM
Friday | 5PM–11PM
Saturday–Sunday | 11AM–10PM

📍 358 N Park Ave suite a, Winter Park, FL 32789

Immerse your taste buds in Italy’s rich array of culinary delights! Prato emphasizes the “Park” of Park Avenue, as its name literally means park in Italian. This gorgeous restaurant has big window-paned doors and year-round patio seating that faces Central Park. Fresh ingredients are key at Prato’s—for freshness and quality standards, the menu may change seasonally or even daily.

Dine with a view, take your date out for some one-of-a-kind pizza and delicious Aperol Spritzes at Prato’s restaurant on Park Avenue. Plus, enjoy happy hours specials on drinks every Monday through Friday, from 4PM–6PM.

Monday–Thursday | 4:30PM–10PM
Friday–Saturday | 4PM–11PM
Sunday | 4PM–10PM

📍 124 N Park Ave, Winter Park, FL 32789

Located inside the Hidden Garden, the Garp & Fuss gastropub offers a quiet, cozy dining space with unique “American fusion” dishes. Their famous “handheld” sandwiches and burgers come in a variety of flavors, including everything from a fried chicken and honey burger to a veggie burger piled high with fresh toppings. 

Have a date night at home and enjoy curbside pick-up and take-out from Garp & Fuss from 4PM–9PM. Included in this deal is 50% off all craft beers and bottles of wine, so be sure to take some home for dinner!

Monday | CLOSED
Tuesday–Thursday | 4PM–11PM
Friday | 4PM–12AM
Saturday | 11AM–12AM
Sunday | 11AM–9PM

📍348 N Park Ave #5, Winter Park, FL 32789

At The Wine Room in Winter Park, experience a new way to sample and try new wines. Purchase a refillable Tasting Card and then wander amongst the vast selection of sample wines, trying any you like. If you love one, swipe your card at our famous self-serve wine-dispensing machines and get a full pour to sit down and enjoy. The Wine Room also has small plates and specialty cheese pairings, making it the perfect stop before dinner or a show on date night. 

The Wine Room is currently open at 50% occupancy and is offering walk-ins for dine-in as well as takeout, curbside pickup, and delivery, so you can explore a world of wine at your own home! Add wine by the bottle or glass to your takeout order…and maybe a sweet treat like their mouthwatering Hazelnut Bombe.

Monday–Thursday | 3PM–9:30PM
Friday–Sunday | 1PM–9:30PM

📍 270 S Park Ave, Winter Park, FL 32789

More Things to Do in Orlando

There are a lot of unique boutiques and restaurants on Park Avenue to discover. Explore every bit of Park Avenue and Winter Park with our Weekend Travel Guides! Or venture out and find other fun plans for date night in nearby Orlando. Here are a few travel guides that we think you would like:

Best Things to Do in Winter Park
Top Date Night Spots in Orlando
Explore the Top Beaches in Florida Close to Orlando
10 Best Pizza Restaurants in Orlando
7 Restaurants in Orlando from Diners, Drive-ins, and Dives You Must Try

Natalie Monzon

Natalie Monzon

Natalie is a City Manager for UNATION and author of the Stuff to Do in Orlando City Guide. For more insight on the best events and things to do in the Orlando area, download the UNATION app and follow @StufftoDoinOrlando on InstagramFacebook, and YouTube.

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