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

by Dani Meyering

A local hub for dining, shopping, and exploring, Park Avenue in Winter Park is no secret to Orlando locals. Offering one of the most refined areas in Central Florida, the avenue of Park 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.

Pro tip: Fall as well as the holiday season are especially lovely here, and complete with charming Christmas light displays.

Updated June 2026

THINGS TO DO AT PARK AVENUE IN WINTER PARK

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. And recently refreshed stage offers community performances, at the north end of the park. Then on the south end of the park is a beautiful rose garden, 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 at Central Park, Winter Park.

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 knowledgeable 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 10 a.m.-4 p.m., and are first come, first served. The cost is $19 per person.

Winter Park Scenic Boat Tour | Image credit: Stephanie Patterson

Important tips:

Bring along some water
10 a.m. and 11 a.m. tours are less busy, so are weekdays
Most of the tour is in the bright sun so dress comfortably
Gratuity for the boat driver is appreciated

SHOPPING AT PARK AVENUE

The shopping is what attracts most visitors to Park Ave. in the first place, with endless boutiques, specialty stores, and upscale offerings that 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.

Gasp Winter Park is just off Park Avenue and is worth the extra steps for the cute, hot pink vibes.
Writer's Block book shop is a must-visit for couples. May we suggest picking out a book to read together? Or pick out a book for each other?
Kathmandu has offered goods from around the world right here on Park Avenue for years.
Frank offers great gifts for those who love interior design and adding a bit of flair to their space

Charles Hosmer Morse Museum of American Art

Located on the north end of Park Avenue, 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 Charles Hosmer Morse Museum of American Art is $8 for adults, $7 for seniors, $3 for students with a valid ID, and free for children younger than 12.

The cheap admission is ideal for couples looking to have a memorable but budget-friendly date night. And even though it is affordable, this place is so beautiful it made our list of impressive date ideas.

EATS AT PARK AVENUE

French Bakeries

Love French pastries? Then you’re in luck. You'll also find oodles of French pastries and delights at Croissant Gourmet, just off of Park Ave. Also, give The Glass Knife a try; we hear their homemade pop tarts are delicious!

Weekend Brunch

Briarpatch is your go-to for breakfast or brunch. Sunday brunch draws a big crowd, so be prepared! Briarpatch also serves lunch if you're not a morning person.

Other ideas for brunching on Park Ave:

Boca Winter Park: Saturdays and Sundays
Hamilton's Kitchen at The Alfond Inn: Saturdays and Sundays

If you love brunch then you've got to check out these Best Restaurants for Brunch in Orlando.

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!) and BoVine Steakhouse for an upscale night out.

For Asian-fusion fare and lovely outdoor dining head to Umi at the south side of Park Avenue. Umi is owned by a husband and wife who infuse their restaurant with global flavors and global decor.

Italian

You can't ever go wrong with pizza, especially on Park Ave. For authentic Italian check out Prato, a rustic Italian eatery. Patro is back from a refresh and is usually home to a great happy hour.

On the south end of Park Avenue is a charming Italian eatery that is authentic and delicious. Grappolo Cucina Italiana recently opened and is swiftly gaining a following.

Related: A Local's Favorite Places for Pizza

Sweets and Desserts

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 taking a bag home, I really mean taking 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. 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

A beautiful sweet spot along Park Avenue is AJ Chocolate House. At the south end of Park Avenue inside AJ Chocolate House you'll find chocolates, specialty coffee, scrumptious cakes, and indulgent breakfast items.

AJ Chocolate House now offers brunch featuring croissant sandwiches paired with a light salad, dressed in chocolate vinaigrette! And you absolutely MUST try the incredible Norwegian Hot Chocolate, layered with dark, white, and milk chocolates.

Norwegian Hot Chocolate AJ Chocolate House Winter Park — Norwegian Hot Chocolate AJ Chocolate House – image by Dani Meyering

DELICIOUS DRINKS AT PARK AVENUE

Barnie's Coffee Kitchen

Location: 118 S Park Ave, Winter Park, FL 32789

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.

The Imperial Winter Park and Winter Park Distillery

Location: 136 S. Park Avenue , Winter Park, FL, United States, Florida

This wine bar is The Imperial's second location in Central Florida; the other is the original in Ivanhoe Village. A furniture store by day and wine bar by night, the menu includes wines, beers, cocktails (thanks to its partnership with Winter Park Distillery), and a food menu of bar snacks and lighter fare.

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