Your Guide to a Perfect Afternoon on Park Avenue in Winter Park

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Park Avenue Winter Park

A local hub for dining, shopping, and exploring, Winter Park's Park Avenue is no secret to Orlando locals. Offering up everything from popcorn drizzled with chocolate to pontoon boat tours, the area is popular for good reason. While small in size, Park Ave. boasts unique eateries, upscale shopping, and multiple cultural activities.

Spend an afternoon discovering what makes Park Ave. so special by choosing a few options from our guide to the area.


Central Park

It may not be a park of NYC proportion, but our local Central Park is a great spot for an afternoon walk or picnic. You'll find a stage at one end and a beautiful rose garden at the other end, with walking paths, large trees, benches, and a fountain in between. Also, be sure to catch Popcorn Flicks in the Park, a free outdoor movie series in collaboration with Enzian usually held on the second Thursday of each month.

Scenic Boat Tour

A convenient and fun way to explore the Winter Park chain of lakes, the Winter Park Scenic Boat Tour is less than a five-minute walk from Park Ave. The tour is a relaxing, 1-hour pontoon boat ride narrated by a knowledgable guide (who will likely provide a steady stream of humorous jokes). You'll cruise along Lake Osceola, Lake Virginia, and Lake Maitland, navigating narrow canals between each lake while learning about numerous estate homes, Rollins College, and Winter Park history. Boat tours run hourly from 10am-4pm and the cost is $16 per person.

Winter Park Scenic Boat Tour | Image credit: Stephanie Patterson


The shopping is what attracts most visitors to Park Ave. in the first place – endless boutiques, specialty stores, and upscale offerings can be found around each corner. For the full Park Ave. experience, combine shopping with another local activity and a meal at one of the area's top restaurants.

Charles Hosmer Morse Museum of American Art

Located on the north end of Park Ave., away from the main hustle and bustle, this art museum is home to a large collection of American art along with an extensive collection of Tiffany glass. Admission to the museum is $6 for adults and FREE on Friday nights November-April, which is ideal for couples looking to have a memorable but budget-friendly date night. 

Other Options:


French Bakeries

Love French pastries? Then you’re in luck. NYC-based French bakery Financier Patisserie serves up an assortment of French pastries and menu items by day and transforms into a charming bistro by night. You'll also find oodles of French pastries and delights at Croissant Gourmet, just off of Park Ave.

French date night in Orlando - Financier Winter Park
Financier Winter Park | Image credit: Stephanie Patterson

Weekend Brunch

Briarpatch is your go-to for breakfast or brunch. Sunday brunch draws a big crowd, so be prepared! Choose from 5 pancake varieties, 6 eggs benedict options, and plenty of other breakfast favorites. Briarpatch also serves lunch if you're not a morning person.

Other ideas for brunching on Park Ave:

  • Boca Winter Park: Saturdays and Sundays from 10am4-pm
  • Hamilton's Kitchen at The Alfond Inn: Saturdays and Sundays from 8am-2pm
  • The Parkview: Saturdays and Sundays from noon-4pm

Romantic Dinner Options

There are so many restaurants on Park Ave that we made a culinary map to outline our favorites for couples. A few highlights include Rome's Flavours for an authentic Italian date night (the pizza is incredible!), Garp & Fuss for courtyard dining, Sushi Pop Winter Park for satisfying your sushi cravings, and BoVine Steakhouse for an upscale night out.

Image credit: Rome's Flavours

Pizza at Prato or Braccia

You can't ever go wrong with pizza, especially on Park Ave. For authentic Italian check out Prato, a rustic Italian eatery serving up creative pizzas like “The Widowmaker.” Prato also offers a great happy hour, or you could follow our Prato + Gelato date night itinerary.

For pizza with a Brazilian twist, take a quick step off Park Ave. to Braccia to enjoy crispy, thin crust pizza in a cozy indoor/outdoor environment. The Chicken with Catupiry (a Brazilian soft cheese) pizza is out of this world.

Sweets at Peterbrooke and Gelato-go

Peterbrooke Chocolatier of Winter Park is small but full of tasty treats ranging from chocolates to gelato and chocolate shoes (yes, really) to chocolate covered popcorn. Speaking of the chocolate covered popcorn, it's a local favorite and bestseller, so make sure to take a bag home with you. And by take a bag home, I really mean take a bag to consume during the car ride home (oops). 

Gelato-go in Winter Park serves up authentic Italian gelato along Park Avenue. All flavors are made fresh in house, and the shop was awarded Best Dessert in the Best of Winter Park 2019 awards. Pair your cup or cone with an espresso and then stroll Park Avenue to awaken each of your senses.

Park Avenue Winter Park date ideas - Gelato-go
Image credit: Arlene Laboy


Barnie's Coffee Kitchen

Located in a picturesque courtyard along Park Ave. known as Greenada Court, Barnie's is where to go to get your coffee fix. They make a great iced latte to help you cool down on those hot late summer days and the breakfast offerings are spectacular.

Imperial Wine Bar

This wine bar is Imperial’s third location in Central Florida. A furniture store by day and wine bar by night, the menu includes wines, beers, cocktails, and a savory food menu.

Park Avenue Winter Park dates - Imperial Wine Bar
Image credit: The Imperial at Washburn Imports Winter Park

The Parkview

Also a fabulous restaurant (with a weekend brunch), The Parkview offers and impressive selection of craft beer and wine. If you visit during brunch, make sure to try the mimosa flight.

Other Options

  • Drinks at The Alfond Inn, located just a short stroll from Park Avenue
  • Sample wines to your heart's content or attend a tasting event at The Wine Room

Florida food and travel photographer and writer Stephanie Patterson

About the Author/Photographer:
Stephanie Patterson is the editor of Orlando Date Night Guide. She’s a talented professional food and travel photographer and writer with a passion for creativity, the beach and great eats. When she’s not taking photos or writing, you can find her exploring the state for her Florida travel blog, Travel Taste Click. Find her online at and


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