Known for its scenic lakes, brick-lined streets, and rich history, it’s one of Florida’s best-kept secrets.
Whether you’re looking for art, food, shopping, or outdoor adventures, Winter Park has a little bit of everything. Here’s what to do when you visit.
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1. Wander Park Avenue
Park Avenue is the heart of Winter Park. This beautiful, tree-lined street is filled with boutique shops, sidewalk cafes, and restaurants.
Whether you’re shopping for home goods, clothing, gifts, or just enjoying a stroll with coffee in hand, this stretch of road is the perfect place to slow down and enjoy the day.
You’ll also find some of the best dining and local events right along this street.
Photo Credit: City Of Winter Park
2. Relax in Central Park
Located right on Park Avenue, Central Park is a gorgeous public space that serves as the town’s social and cultural hub.
It’s the ideal place for a picnic, a book break, or just enjoy the outdoors.
You’ll often find events happening here throughout the year, such as concerts, outdoor art festivals, or farmers’ markets.
The fountain, flowers, and shaded benches make this park especially inviting on a sunny Florida afternoon.
3. Take the Winter Park Scenic Boat Tour
One of the most unique ways to experience Winter Park is from the water.
The Winter Park Scenic Boat Tour takes you on a one-hour narrated ride through the town’s chain of lakes and canals.
As you ride across the water, you’ll pass historic homes, Rollins College, and lush tropical landscapes.
It’s peaceful, informative, and gives you a fresh perspective on the town’s beauty.
The tour departs daily and is a top-rated attraction for first-time visitors. This was also my favorite activity in Winter Park.
Photo Credit: Morse Museum
4. Visit the Charles Hosmer Morse Museum
This museum is home to a collection of works by Louis Comfort Tiffany.
From stained-glass windows and lamps to jewelry and an entire chapel interior, the collection here is breathtaking.
It’s a quiet place where you can appreciate American decorative art in a beautiful, well-curated setting. If you enjoy art or design, this is a must-see.
Photo Credit:Polasek Museum
5. Explore the Albin Polasek Museum and Sculpture Gardens
Located on the shores of Lake Osceola, this lakeside museum showcases the life and work of renowned sculptor Albin Polasek.
Visitors can walk through the sculpture garden and enjoy peaceful views over the water while admiring the artist’s work.
It’s a hidden gem that adds an artistic touch to any Winter Park itinerary.
6. Indulge in Winter Park’s Dining Scene
Winter Park is home to some of the best restaurants in Central Florida.
If you’re visiting for brunch, Briarpatch is a local favorite with dishes like raspberry-brie French toast that are as delicious as they are Instagram-worthy.
For dinner, check out Prato, known for its handmade pasta and stylish atmosphere.
If craft beer and gourmet pub food are more your style, The Ravenous Pig offers a full gastropub experience with locally brewed beer and seasonal fare.
We ate at Bar Italia and enjoyed their options such as pizza, meatballs, bread, and chicken parmesan.
The variety of dining options makes Winter Park a great Florida dining destination.
7. Spend an Afternoon at Winter Park Village
Winter Park Village is a modern shopping and dining district located just a few minutes from Park Avenue.
It offers a mix of national retailers and local businesses, along with a movie theater and restaurants.
Whether you’re shopping, catching a film, or relaxing on an outdoor patio with a drink, Winter Park Village is a great place to spend a few hours.
It has a slightly more contemporary vibe than downtown, but still reflects the overall charm of the area.
Photo Credit: City Of Winter Park
8. Discover Kraft Azalea Garden
If you’re looking for a quiet outdoor space, Kraft Azalea Garden is one of the most peaceful spots in Winter Park.
Tucked away on the shore of Lake Maitland, the park is shaded by massive cypress trees and offers awesome views across the water.
It’s a favorite location for weddings and photoshoots, but also a great place to relax with a coffee or take a quiet morning walk.
9. Learn Local History in Hannibal Square
Hannibal Square is a historic African-American neighborhood in Winter Park, and it’s an important part of the town’s culture.
The Hannibal Square Heritage Center offers exhibits and oral histories that honor the legacy of the area’s residents.
Today, the neighborhood also features cafes, shops, and public art installations that blend history with community life.
It’s a meaningful place to visit and reflects the town’s diverse heritage.
10. Attend One of Winter Park’s Seasonal Events
Winter Park is known for its well-organized festivals and community events.
The Winter Park Sidewalk Art Festival, held in March, is one of the most prestigious outdoor art shows in the country.
In October, the Autumn Art Festival highlights Florida artists and draws locals and visitors.
There’s also the festive “Dinner on the Avenue” event, where long tables are set up down Park Avenue for a one-night, open-air dining experience that celebrates local food and community.
Final Thoughts on Visiting Winter Park
When it comes to Florida, Winter Park offers the best of both worlds—quiet, scenic streets and lakes mixed with high-quality art, food, and culture.
Whether you’re coming for a day trip or a full weekend getaway, Winter Park has plenty to keep you entertained without the crowds or chaos of other Florida destinations.
From the beauty of the lakes and gardens to the unforgettable boat tours, top-tier restaurants, and small-town atmosphere, Winter Park truly earns its reputation as one of the best small towns in Florida.
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Booking a last-minute trip to Florida?
If so, we have you covered. Here are some top recommended tours and experiences!
Top Tours in Florida – Viator
Top Hotels In Florida – Booking.com
Looking To Get Around In Florida?
Check out rental car rates here! 🚗
