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

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.


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 $14 per person.

Park Avenue Winter Park scenic boat tour

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 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. A free cell phone audio tour is available every day for the Laurelton Hall exhibition.

Park Avenue Winter Park
Casa Feliz

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. Keep your eyes out for Paul’s Poems (he’s there Fridays 5-10pm) – pick any topic and Paul will write a poem for you on his typewriter. Also, be sure to catch Popcorn Flicks in the Park, a screening of classic movies in collaboration with Enzian usually held on the second Thursday of each month.

Other Options


Breakfast/Brunch at Briarpatch
Open daily from 7am-5pm (8am on Sundays) 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.

park avenue winter park
Credit: Kristen Manieri

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.” 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.

Park Avenue Winter Park

Sweets at Peterbrooke
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). Follow them on social media to find out about the chocolate classes they host a few times each year.

Walking Food Tour
For a taste of multiple local eateries all in an afternoon’s time, Orlando Food Tours offers food tours of the area with six yummy stops along Park Ave. In addition to food, you’ll also stop at a few historical and cultural points of interest during the three-hour tour.


park-station-cocktailsBarnie’s Coffee Kitchen
Located in a picturesque portion of 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 their breakfast offerings are spectacular.

Park Station
For craft cocktails, make a stop at Park Station. They make a mean Moscow Mule if you’re a fan of ginger, and have a full bar if nothing on the cocktail menu sparks your interest. The drinks are a bit on the pricier side, but this is still a nice spot for a drink or two. Visit during happy hour (4-7pm) to save on cocktails and select food items.

The Parkview
Also a fabulous restaurant (with awesome brunch on the weekends), The Parkview always has a wonderful selection of craft beer on tap for beer lovers and loads of wine options for wine lovers. If you visit during brunch, make sure to try the $10 mimosa flight.

Other Options

  • Drinks or Happy Hour at The Alfond Inn, located just a short stroll from Park Avenue. On cool days, they have the outdoor firepits lit, making for a wonderful way to enjoy the nip in the air.


Florida food and travel photographer and writer Stephanie Patterson

About the Author/Photographer:
Stephanie Patterson is the managing 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

Photo credit: Stephanie Patterson unless otherwise stated


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