9 Unique Experiences in Winter Park, Florida

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Winter Park is a beautiful mix of unique experiences. Known for tourism and as a famous snowbird town, it maintains a quaint small-town feel with its winding brick streets and canopies of live oak and camphor trees covered in Spanish moss. There’s no better place to beat the winter cold than Winter Park, Florida. 

About Winter Park, Florida

Located less than ten miles north of Orlando, Florida, Winter Park is a well-known gem. This resort community includes a great deal of outdoor recreation space for every age, including biking trails and many parks for your relaxation and exercise activities. Its main street, Park Avenue, has a wide variety of dining options, art galleries, shops, and other entertainment venues.

After the railroad came into town around the late 1800’s, Winter Park developed quickly. Since then, Winter Park has been a popular destination. With a current population of just over 30,000 people, it seems to be a small town.

However, in the winter months, the population rises with all the tourists that arrive to enjoy the area, including the world-famous Walt Disney World Resort. Still, it manages to maintain its small-town vibe, even then.

Best Time of Year to Visit Winter Park, Florida

Some of the best times to visit Winter Park, Florida, is during early spring from March to May and then again from October to December. Temperatures average between 70 to 80 degrees with less than two inches of rain.

These months are the most comfortable — it’s not too rainy, cloudy, or muggy. It might seem as though it’s perfect. Keep in mind, though, the best weather brings more people. So, if you don’t mind the heat, you might want to visit when there are fewer visitors. 

9 Unique Experiences in Winter Park, Florida

We’ve got nine experiences unique to this town. There’s something for everyone in this quaint Florida town, from museums to a craft distillery to water activities and botanical gardens.

Albin Polasek Museum & Sculpture Gardens

Address: 633 Osceola Ave., Winter Park

This historic site overlooks Lake Osceola and sits on three acres of beautiful land. Albin Polasek is an internationally acclaimed Czech sculptor. Here you can explore Polasek’s landmark home, his sculptures, and peaceful gardens.  You can tour the gardens and museum on your own or via a guided tour. 

The gardens and museum are designed to inspire creativity and peace. The curators hope that you’re encouraged to create art and unleash your creative side.

The Brewstillery

Address: 1288 N. Orange Ave., Winter Park

Bear and Peacock Brewery and Winter Park Distilling Company make up what’s known as the Brewstillery.

The first craft distiller in Orange County came into existence in 2010.  Starting with a homemade 50 gallon still, Winter Park Distilling Company has grown into its own with its handcrafted bourbons and dark rum. Offering patrons whiskey, rum, vodka, and bourbon at the Brewstillery, you can come in for a taste or a bottle to go.

Bear and Peacock Brewery opened in the shared space in 2016 by the same owners of the distillery.  Recognizing the need for both, they serve craft beers on 12 taps in the elegantly designed taproom space.

Casa Feliz Historic Home Museum

Address: 656 N. Park Ave., Winter Park

Also known as the Robert Bruce Barbour House, this is a restored Spanish Farmhouse. Designed by the famous architect James Gamble Rogers II, this historic home is majestic in its simplicity and stories it has to tell.

Known as the Crown Jewel in this city of homes, Casa Feliz or the Happy House currently sits proudly above the golf course overlooking the city.  The house faced possible demolition in 2000, and the community rallied to have it restored, which meant it also had to be relocated.

Today, this farmhouse serves the community as a historical museum and a popular event space and has become more than just a farmhouse. It now holds a piece of Florida’s heart.

Prometheus Esoterica

Address: 1740 FL-436, Winter Park

Billed as a macabre dreamland to satisfy your darkest desires, Prometheus Esoterica is a store you’ve never visited before. You’ll find many interesting trinkets here focusing on medical science, natural history, religious antiquities, and much more. They will either entice you or chill you to the bone.

Often described as a serial killer speakeasy, this one-of-a-kind store is found only in Winter Park. That just might be reason enough to pay a visit to this quaint and curious town. Maybe you’ll even get a chance to meet the evil geniuses behind this place. The husband and wife team must have some sort of a twisted mind.  

Charles Hosmer Morse Museum of American Art

Address: 445 N. Park Ave., Winter Park

The Charles Hosmer Morse Museum is well known for its comprehensive collection of Louis Comfort Tiffany’s art. His art includes jewelry, pottery, paintings, and glass-making designs. You’ll also see other American artists from the late 19th and early 20th centuries, including American paintings, graphics, and all types of decorative arts.

Adult tickets are $6. But don’t just come to explore the museum, as they also host various exhibits and community events that rotate throughout the year.

Take a Scenic Boat Tour

Address: 312 E. Morse Blvd., Winter Park

This scenic boat tour is for nature and city lovers alike. The pontoon boat is set up for a comfortable one-hour boat ride through three of the seven lakes that make up the Chain of Lakes in Winter Park. You’ll also get to experience two narrow man-made canals giving you more opportunity to explore the area.

Your tour will take you through the luscious tropical landscapes of palms, ferns, cypress trees, and tropical flowers. Along the way, you might catch a glimpse of an elegant crane or a sunbathing alligator. Adult tickets are $14, and be sure to have cash or check on hand as they do not take credit cards.

Take a Self-Guided Cultural Walking Tour

You can explore the town on your own or download a guided tour using the app “GPSmyCity: from iTunes App Store or Google Play to your mobile phone or tablet. The app becomes your personal tour guide as it walks you through one stop to the next using the GPS services on your phone.

Starting at Casa Feliz Historic Home Museum and making your way to the Morse Museum, you’ll learn about the culture and Winter Park history.  You can then stroll along Park Avenue, where you can explore over 140 boutiques, sidewalk cafes, museums, and world-class restaurants.

From there, you’ll make your way to the Winter Park Historical Museum for free exhibits that preserve the city’s story.  Continue your walking tour by visiting the beautiful All Saints Church and the Annie Russell Theatre, the longest-running theatre in Florida.

The last stop is the Knowles Memorial Chapel, the centerpiece of the Rollins Campus known for its stunning stained glass features. Or make the last visit back at Park Avenue for an evening at its many taverns and wine bars.

Visit Mead Botanical Garden

Address: 1300 S. Denning Dr. Winter Park

Wander 47 acres of this gorgeous natural habitat with free admission. You’ll experience tranquility within an urban setting that’s unique to Winter Park. Choose from hiking trails or walking the boardwalk. You can visit the greenhouse, the butterfly garden and the pond that is home to many turtles, birds, and fish.

If you’re more inclined to join an event in the garden, there’s tai chi or yoga classes. Or try your skill at learning how to identify mushrooms.  Also a popular event space for weddings, concerts, and summer camps for kids, there’s no shortage of entertainment at the Mead Botanical Garden.

Rent a Kayak on Lake Virginia

Request a rental online or call today: 407-416-4076

There’s nothing quite like spending the day on the water, except maybe spending it on a kayak or paddleboard.  With two launch sites available, your day can be your own. One is Dinky Dock off of Ollie Avenue near Rollins College on Lake Virginia, and the other is at Fort Maitland Park on Lake Maitland.

You can rent for a half or full-day, and all options offer the choice to sit or stand, making it perfect for fishing, paddling, or just relaxing. You’ll make your way around the Winter Park Chain of Lakes connected by navigable waters.  Seek out the canals, too, as those are quite peaceful and offer the chance to view native wildlife and a respite from the wind and sun.

Traveler’s Tip: Learn how to fit in like a local when you stop in to Orlando, Fla.

Culture and Adventure Awaits You

With so many activities and experiences unique to Winter Park, your time spent here will be full of culture and adventure. This quaint Florida town is full of wonders to explore, food to eat, and nature to lose yourself in. So much so, you might be asking yourself why you ever left to go to Disney World.

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