Cobbled-stoned streets, narrow alleyways, and gorgeous buildings, Winter Park, Florida has several museums, restaurants, and fun activities for the whole family.
In this article, you’ll find the top 20 things to do in Winter Park, FL, and why this should be on your list for your next trip to Florida.
Top 10 Free Things to Do
Winter Park is full of gems! From the Casa Feliz to Hannibal Square, here are 10 free things you can do.
1. Visit Mead Botanical Garden
If you’re looking for a free garden to visit in Winter Park, Florida, Mead Botanical Garden is the one to go to. This is one of my favorite botanical gardens. With its lush greenery, vibrant flowers, and serene water bodies, Mead Botanical Garden is a paradise for nature lovers.
Tips for Visiting
✨ The garden is open every day from 8 to dusk, and it’s free to enter.
✨ Bring your camera and capture the beauty of the garden. You might spot some turtles, fish, wading birds, or butterflies
✨ The garden hosts various events and activities throughout the year, such as yoga classes, plant sales, concerts, and workshops. Check out their website for more information.
Address: 1300 S Denning Dr, Winter Park, FL 32789
2. Watch a Performance at Casa Feliz
Casa Feliz is not just a historic home museum, but also a beautiful wedding venue. The Andalusian-style masonry farmhouse has become one of the most popular spots for photos and weddings. When a wedding isn’t taking place, tours take place every Tuesday and Thursday from 10 a.m. to noon.
On the second Sunday of each month, Casa Feliz also has Music at the Casa, which features different musicians each month at this beautiful historic home, free of charge.
3. Rollins Museum of Art
If you find yourself strolling around Rollins College or Downtown Winter Park, head over to the Rollins Museum of Art. While this is a small museum compared to others, the Rollins Museum of Art offers quite a wonderful collection of art. Depending on the exhibit, some will be interactive and fun, while others will cause you to do a double-take. It’s a great way to spend some time indoors, especially when it’s summer.
4. Morse Museum of American Art
While this museum usually has an entrance fee, they do have free Fridays from 4 p.m. to 8 p.m. However this only happens from November through April. The Morse Museum of American Art is quite a popular museum and the reason for it is because it houses the most comprehensive collection of works by Louis Comfort Tiffany. This is a stunning museum to visit and one you shouldn’t skip out on.
Address: 445 N Park Ave, Winter Park, FL 32789
5. Winter Park History Museum
The Winter Park History Museum is an excellent stop for anyone wanting to learn more about the history of Winter Park.
This is where I learned about the Langford Hotel. The Langford Hotel was closed in May 2000, but it is forever an iconic hotel that once stood where the Alfond Inn stands now.⠀
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This hotel had all sorts of guests, including Mamie Eisenhower, June Carter Cash, Walt and Roy Disney. It was popular with many tourists not only for its tropical appeal but also because it ran year-round unlike the other hotels that would close during the summer (this was when it first opened).
Address: 200 W New England Ave, Winter Park, FL 32789
6. Kraft Azalea Gardens
While this is a small garden, it is still a beautiful place to visit. This 5.22-acre public garden is open year-round, and it is a great place to enjoy the shade provided by the enormous cypress trees. It’s also a great wedding venue since it has the beautiful Exedra as a backdrop.
Address: 1365 Alabama Dr, Winter Park, FL 32789
7. Stroll around Hannibal Square
This is one of those places that many of the tourists don’t seem to know about. Mostly because downtown Winter Park is the popular spot, but Hannibal Square has quite a bit to offer. From the history surrounding this place to the quaint little park, this is a beautiful place to visit full of restaurants and shops.
Address: 511 W New England Ave, Winter Park, FL 32789
8. Stroll around Downtown Winter Park
Downtown Winter Park is one of my favorite places to visit in Orlando. It has so much to offer, from amazing restaurants and shops to beautiful parks and museums. Here are some of the things I love about this charming neighborhood:
Address: 110 N Park Ave, Winter Park, FL 32789
9. Check out The Alfond Inn
I have been to numerous events at the Alfond Inn and I am always impressed by the food, the event spaces, and the hotel in general. This beautiful hotel also has a collection of art in the lobby, and you do not need to stay there to check them out. Some of this collection can also be found at the Rollins Museum of Art.
10. Visit Rollins College
There are so many gems around Rollins College! So if you’re in Winter Park, take a stroll around Rollins College and check out some of these “hidden” gems.
Things to see:
For more check out my YouTube video!
Address: 1000 Holt Ave, Winter Park, FL 32789
Top 10 Things to do
While there are plenty of free things to do in Winter Park, FL, some of the best things to do are not. Here are a few things to do that cost money but are worth visiting.
11. Scenic Boat Tour
Nothing like a scenic boat tour to enjoy the beauty of Winter Park. The lake views, the historic homes, the canals… it’s all amazing! If you haven’t already taken a tour with Scenic Boat Tour, then be sure to add this to your Florida bucket list!
You’ll go through canals, under bridges, see beautiful homes, and learn more about charming Winter Park!
Address: 312 E Morse Blvd, Winter Park
12. Albin Polasek Museum & Sculpture Gardens
Winter Park has quite a selection of museums, but out of the many we have, Albin Polasek Museum & Sculpture Gardens is unique. Aside from checking out the indoor museum which was once Albin Polasek’s home, they have an impressive collection of sculptures in the gardens plus you get a beautiful view of the grounds and home.
Address: 633 Osceola Ave, Winter Park, FL 32789
13. Harry P Leu Gardens
This is another beautiful garden we have in Winter Park, but unlike its free counterpart, the Harry P Leu Gardens does have an entrance fee. The gardens at Harry P Leu Gardens are amazing though and if you go during one of their themed exhibits, you might just see fairy doors or dinosaurs in the garden.
Address: 1920 N Forest Ave, Orlando, FL 32803
14. AJ Chocolate House
There are so many different brunch spots in Winter Park, but what I love about AJ Chocolate House is the variety of chocolate they have! They have all sorts of chocolate treats to choose from and they are absolutely delicious. Founded in Lithuania, this is their first store in the U.S.
Address: 522 South Park Ave, Winter Park, FL 32789
15. Orlando Science Center
This is such a fun place to take the kids and even if you don’t have kids, it’s still an impressive science center to check out. They also have events such as Science Night Live, which is an event for adults.
Address: 777 E Princeton St, Orlando, FL 32803
16. Brunch at the Many Restaurants
Winter Park has a plethora of restaurants to choose from. Whether you find yourself in a historic downtown or one of the neighborhoods. Brunch in Winter Park is a must!
One of my favorites is MAYA CAFE Lounge & Gallery. This cafe is a visual treat, with colorful decor and a red Corvette in the middle of the dining room. Aside from being absolutely stunning with all the beautiful pieces decorating the shop, the food is also quite delicious!
Right next to it, you’ll also find the food truck La Patrona!
Address: 1980 Howell Branch Rd., Winter Park, FL
17. Orlando Museum of Art
If you’re looking to explore more museums in the area, the Orlando Museum of Art is one you should check out. They usually have some fun exhibits to check out, my favorite being the display of Christmas trees that are on display during the holidays.
Address: 2416 N Mills Ave, Orlando, FL 32803
18. The Axe Trap
Looking for something fun to do in Winter Park? Then check out The Axe Trap!
The Axe Trap has it all: cocktails, food, and fun! Don’t miss their ladies night on Thursdays with $10 cocktails.
Address: 2600 Lee Rd, Winter Park, FL 32789
19. The Winter Park Playhouse
This is unlike any theatre I’ve been to. The Winter Park Playhouse is more intimate and you’ll find some great musical comedies and cabarets year-round.
Address: 711 Orange Ave Ste C, Winter Park, FL 32789
20. Paddleboard through canals
Paddleboard Orlando offers the opportunity to paddleboard through the Venetian canals in Winter Park. So if you’re looking for something more adventurous than the boat tour, this is something worth doing.
Address: Dinky Dock Park – 410 Ollie Ave, Winter Park, FL 32789
