We independently research and recommend any products or places but we may earn a commission if you click on links we provide. Learn More.
What was once an exclusive resort for the well-to-do in the 1800s is now a much-loved city whose magic has continued to draw in visitors from near and far. Winter Park is a suburb of the nearby Orlando, and it’s no surprise that visitors continue to flock here when in need of a little break from the big city.
Known for its plethora of pristine parks and beautiful lakes, the town is a nature lover’s dream. There is also an impressive collection of museums, award-winning restaurants, and a great display of historic architecture.
Whether you’re coming from nearby Orlando or further afield, Winter Park is a destination in its own right. There’s even an Amtrak stop here, making it a convenient day trip or weekend getaway.
Here are some of the best things to do in Winter Park, Florida.
Take A Scenic Boat Tour
Take a ride through Winter Park’s beautiful chain of lakes on a scenic and historic boat tour. Operating since 1938, the city’s scenic boat tour is the perfect introduction to this stunning area.
The tour takes you through the canals and lakes on a small pontoon boat, and a guide will point out all the noteworthy attractions along the way, including Rollins College, parks, museums, and opulent mansions. As you float, you’ll also see trappings of the wild area that this once was, with overhanging trees, lush vegetation, and scores of waterfowl and other wildlife.
Tours run every day year-round, making this one of the best things to do in Winter Park no matter what time of year you’re in town.
Albin Polasek Museum
Even if you’ve never heard of Albin Polasek (chances are, you haven’t), a visit to the Albin Polasek Museum is one of the best things to do in Winter Park.
This is part museum and part sculpture garden, and you can tour the artist’s former home before exploring the impressive sculpture garden out back. The home features original furnishings and over 200 pieces of Polasek’s work. The garden faces Lake Osceola, and if you’re lucky, you may be in town for one of the cultural events hosted here throughout the year.
Walk Around Downtown
No trip to Winter Park is complete without a stroll through the charming downtown area. Park Avenue is the town’s elevated version of Main Street, with boutique shops, upscale jewelry and furniture stores, and tons of restaurants.
As you peruse Park Ave, you’ll come across a number of cultural landmarks, including Rollins College, Hannibal Square, and Central Park – home to the famous Saturday morning Farmers Market.
The downtown area is the perfect place to amble along without any plans in mind, and once you’re ready for a break, you can pop into a restaurant, stop for a glass of wine, or visit the gourmet chocolatier!
Charles Hosmer Morse Museum Of Art
While you’re downtown, be sure to check out the Charles Hosmer Morse Museum of Art. The museum houses one of the most comprehensive collections from Louis Comfort Tiffany, a renowned artist who dabbled in various mediums, including paintings, pottery, jewelry, and, most famously, glass.
The newest exhibition features glass panels that were saved from the artist’s Long Island mansion, which burned down in 1957. There are many exhibitions inside this large museum, so be sure to block out a good chunk of time to discover the works of an artist whose life goal was “the pursuit of beauty.”
Mead Botanical Garden
One of the best free things to do in Winter Park, Florida, is visiting Mead Botanical Garden. This 47-acre garden is full to the brim with lovely landscapes, from colorful planters along paved paths to towering trees along scenic hiking trails.
The wetland ecosystem plays host to a variety of creatures like turtles and waterfowl, and there’s even a butterfly garden on-site. This urban oasis sits a few miles from downtown Winter Park, but it’s easily accessible by foot or by car.
Enjoy A Day At The Central Park
Central Park sits in the heart of Winter Park, Florida and offers 11 acres for relaxing, gathering, and strolling. Of all the parks in the city, Central Park takes the cake in terms of location and foliage, with lovely purple wisteria blooming throughout the spring. There’s also a rose garden on the southeast end of the park, plus several fountains and lots of shady oak trees encircling the entire area.
In addition to the inviting atmosphere, this lush setting also hosts a variety of events throughout the year, including a weekly Saturday farmer’s market, an autumn art festival, a Fourth of July celebration, and more.
Sample Local Restaurants
Winter Park is chock-full of great restaurants, and what better way to get a taste of a place than by, well, having a taste of the food!
Park Avenue is one of the best places to eat in Winter Park. In addition to the array of great shops, there are also tons of places to sit down and get some great grub. You’ll find everything from adorable coffee shops to swanky sit-down restaurants here, and there are tons of other options all around town to satisfy any craving.
Visit The Shops
It should come as no surprise that a former swanky resort town has a great shopping district. Park Avenue is the main drag in town, and it’s hands down the best place to head if you want to shop ’til you drop.
This upscale avenue is lined with both one-of-a-kind boutiques and well-known shops, selling everything from luxury home decor to cosmetics and everything in between. Once you’re all shopped out, you’ll find a variety of restaurants and cafes up and down the entire avenue.
Rollins College is often regarded as one of the most beautiful campuses in the country, so don’t miss your chance to see it while you’re visiting Winter Park. The sprawling campus overlooks Lake Virginia and boasts lovely historical buildings, several parks, and a free art museum.
The Rollins College Museum of Art gets top marks for both quality and quantity – there are over 5,000 works in the collection in a variety of mediums from many different time periods, from the early Renaissance to contemporary works.
Kraft Azalea Gardens
If you’re looking for something a little more off the beaten path, make your way to Kraft Azalea Gardens. Situated just a mile north of downtown Winter Park, these lesser-known gardens feature trails through the public garden plus more paths through the park beyond. There’s also a small dock for fishing, a great egret rookery, and a photogenic temple styled with ancient Greece in mind.