15 Top things to do in Winter Park, Florida

Students entering Rollins College campus entrance | top things to do in winter park
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Looking for a vacation destination that is not packed with tourists? Winter Park might just be the spot for you!

Did you know that Winter Park is a small town in Florida known as one of the coolest suburbs in America? The city is comprised of just over 28,000 people. Talk about small town charm!

Commonly recognized for its scenery, Winter Park is packed full of beautiful trees, lakes, and parks. Along its charming cobblestone streets, you will find museums, locally owned shops, and historical homes.

Here are some of the top things to do in Winter Park worth visiting:

1. Love history? Check out the Charles Hosmer Morse Museum of American Art

The Charles Hosmer Morse Museum of American Art | top things to do in winter park

The Charles Hosmer Morse Museum of American Art | The Charles Hosmer Morse Museum of American Art, Facebook

The Charles Hosmer Morse Museum of American Art | Isabella Thalheimer, YouTube

Charles Hosmer Morse Museum of American Art is where Louis Comfort Tiffany’s (1848–1933) work is still on display. From paintings and pottery to windows and much more, you’ll find the magnificent art Tiffany is most well known for.

Most of the items on display in the museum were from Louis Comfort Tiffany’s own home workshop in Long Island. His pieces are a unique piece of antiquity on display for all to enjoy. Whether you are into art or history, this museum can be an inspiration to all who visit.

The Charles Hosmer Morse Museum of American Art
445 North Park Avenue | Winter Park, FL 32789
Admission: $6 for adults, $5 for seniors age 60 and older, $1 for students and free for children younger than 12
Ph: +1 407-645-5311
Get directions

Best place to eat nearby according to locals and visitors:
• Hillstone Restaurant (4.5/5 stars, American, $$$)
• El Potro Mexican Restaurant(4.5/5 stars, Mexican, $$)
• The Osprey Tavern (4.6/5 stars, New American, $$)

See the full list of places to eat near The Charles Hosmer Morse Museum of American Art.

The best hotel to stay near The Charles Hosmer Morse Museum of American Art based on overall price, location and amenities according to travelers:

The Alfond Inn at Rollins College (9.2/10 stars, $$$) – Booking.com

2. Discover the greatest finds at Park Avenue shopping district

Group of friends gathering outside of a mall at Park Avenue | top things to do in winter park

Group of friends gathering outside of a mall at Park Avenue | Park Avenue, Winter Park, Facebook

Second of our list of things to do is Park Avenue – one of the great appeals of Winter Park. This area is full of small shops, unique boutiques, and some of the best restaurants in all of Florida. Each season, the city organizes different activities, like parades and festivals, for locals and visitors alike to enjoy. This hidden gem in Florida allows tourists to find the best food and shopping experience around.

Park Avenue
151 W. Lyman Avenue Winter Park, Florida 32789
Admission: Free
Ph: (407) 644-8281
Get directions

Best place to eat nearby according to locals and visitors:
• Sushi Pop Winter Park (4.6/5 stars, Restaurant, $$$)
• Café de France (4.5/5 stars, French, $$)
• Due Amici Pizzeria (4.7/5 stars, Restaurant, $$)

See the full list of places to eat near Park Avenue.

The best hotel to stay near Park Avenue based on overall price, location and amenities according to travelers:

Park Plaza Hotel (8.5/10 stars, $$$) – Booking.com

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3. Shop ‘til you drop at the Farmers Market

Fruits and vegetables displayed at Winter Park's Farmers Market | top things to do in winter park

Fruits and vegetables displayed at Winter Park’s Farmers Market | PauloAlmeidaPhotography, Shutterstock

Located in the old train depot on West New England Avenue, Winter Park’s Farmers Market is the source of enjoyable shopping for many in the area. From fruits and veggies to flowers, baked goods, soaps, coffee and much more, this site allows you to enjoy grocery shopping at its finest.

Each Saturday, from 7 am until 1 pm, the farmer’s market opens its doors to allow visitors to browse its products. You’ll find everything your heart might desire because this market is known as one of the best farmer’s markets in Central Florida.

Winter Park’s Farmers Market
200 W New England Ave, Winter Park, FL 32789, United States
Admission: Free
Ph: +1 407-599-3397
Get directions

Best place to eat nearby according to locals and visitors:
• Siam Garden Restaurant (4.5/5 stars, Thai, $$$)
• Deadly Sins Kitchen (5/5 stars, Restaurant, $$)
• Sixty Vines (5/5 stars, Restaurant, $$)

See the full list of places to eat near Winter Park’s Farmers Market.

The best hotel to stay near Winter Park’s Farmers Market based on overall price, location and amenities according to travelers:

Homewood Suites by Hilton Orlando-Maitland (9.3/10 stars, $$$) – Booking.com

4. Soak up the sun at Lake Virginia

Lake Virginia Florida long exposure | top things to do in winter park

Visiting Lake Virginia, fun things to do in Winter Park, FL | Joseph Thomas Photography, Shutterstock

Winter Park is bordered by many bodies of water, but Lake Virginia is one that draws many crowds. This beautiful piece of nature is an attraction for tourists and locals year round. Enjoy your vacation by spending some of your time not just by the lake, but on the lake. Boat and kayak rentals are available so you can spend the day on or in the water.

Lake Virginia
Winter Park, FL 32789 USA
Admission: Free
Ph: 407-691-7829
Get directions

Best place to eat nearby according to locals and visitors:
• 1803 Pizza / Kitchen (4.9/5 stars, Pizza, $$$)
• Rome’s Flavours (4.6/5 stars, Italian, $$)
• Luma on Park (4.5/5 stars, American, $$)

See the full list of places to eat near Lake Virginia.

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The best hotel to stay near Lake Virginia based on overall price, location and amenities according to travelers:

Residence Inn by Marriott Orlando Downtown (8.9/10 stars, $$$) – Booking.com

5. Discover the beauty of Albin Polasek Museum & Sculpture Gardens

Polasek Museum and Sculpture Gardens, in Winter Park, Florida

Polasek Museum and Sculpture Gardens, in Winter Park, Florida | Ebyabe, Wikimedia Commons

Albin Polasek Museum & Sculpture Gardens | Albin Polasek Museum, YouTube

The famous works of Albin Polasek, a Czech sculptor who resided in Florida, can be found in the Albin Polasek Museum and Sculpture Gardens. The Museum was founded in 1961 and was recently added to the United States National Register of Historical places. It contains over 200 pieces of Polasek’s art!

Stations of the Cross by Polasek | top things to do in winter park

Stations of the Cross by Polasek | Albin Polasek Museum & Sculpture Gardens

Visit this unique museum to explore diverse, beautiful art while also taking in some of the local history found in Winter Park.

Albin Polasek Museum & Sculpture Gardens
633 Osceola Ave, Winter Park, FL 32789, United States
Admission: Members and children 4 and under are free; Adults $10; Seniors (60+) $8; College Students with ID $8; Students (K-12) $3
Ph: +1 407-647-6294
Get directions

Best place to eat nearby according to locals and visitors:
• The Hangry Bison (4.5/5 stars, American, $$$)
• China Moon (4.6/5 stars, Chinese, $$)
• Adriatico Trattoria Italiana (4.7/5 stars, Italian, $$)

See the full list of places to eat near Albin Polasek Museum & Sculpture Gardens.

The best hotel to stay near Albin Polasek Museum & Sculpture Gardens based on overall price, location and amenities according to travelers:

Sheraton Orlando North Hotel (8.5/10 stars, $$$) – Booking.com

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6. Take a stroll in Central Park

Winter Park Central Park | top things to do in winter park

Winter Park Central Park | Central Park, Facebook

Central Park , Winter Park FL | Eamor Homes, YouTube

Central Park is one of Winter Park’s finest. Located in the heart of downtown, Central Park offers a comfortable oasis for all of its visitors. On special occasions, you’ll find a ton of events in the park; from festivals to parades, there is fun for everyone! This park has an appeal that will leave you feeling at ease.

Central Park
150 W Morse Blvd, Winter Park, FL 32789, United States
Admission: Free
Ph: +1 407-599-3334
Get directions

Best place to eat nearby according to locals and visitors:
• Bolay (4.7/5 stars, Restaurant, $$$)
• Toasted – Winter Park(4.5/5 stars, American, $$)
• Blended Bistro & Boba (4.7/5 stars, Restaurant, $$)

See the full list of places to eat near Central Park.

The best hotel to stay near Central Park based on overall price, location and amenities according to travelers:

Thurston House Bed & Breakfast (9.8/10 stars, $$$) – Booking.com

7. Learn about Winter Park’s history at Hannibal Square Heritage Center

The Community Pride Mosaic Mural across the street from the Heritage Center | top things to do in winter park

The Community Pride Mosaic Mural across the street from the Heritage Center | Hannibal Square Heritage Center

Hannibal Square Heritage Center | therestoforlando, YouTube

Hannibal Square Heritage Center has a wide variety of art, beautifully displaying the history of Winter Park and its surrounding areas. All of the art is worth a look; however, most visitors are particularly taken by the African American art. It has a lot to offer, such as dining, gifts, shops, etc., there is also a center that might be of interest to you.

Hannibal Square Heritage Center
642 West New England Avenue, Winter Park, FL 32789
Admission: Free
Ph: +1 407-539-2680
Get directions

Best place to eat nearby according to locals and visitors:
• Farm & Haus (4.7/5 stars, Restaurant, $$$)
• The Tap Room at Dubsdread (4.6/5 stars, American, $$)
• Shin Japanese Cuisine (4.5/5 stars, Japanese, $$)

See the full list of places to eat near Hannibal Square Heritage Center.

The best hotel to stay near Hannibal Square Heritage Center based on overall price, location and amenities according to travelers:

Comfort Suites Downtown (8.4/10 stars, $$$) – Booking.com

8. Discover even more about Winter Park at its History Museum

Princess of the Peacocks children's show at Winter Park History Museum | top things to do in winter park

Princess of the Peacocks children’s show at Winter Park History Museum | Winter Park History Museum, Facebook

This historical museum is home to the glorious and diverse past of Winter Park. Displaying and preserving the history of Winter Park and the surrounding areas, this museum will put a smile on the faces of all history buffs. If you are someone who loves to learn, who enjoys history and likes looking at historic relics, Winter Park History Museum is the place for you!

Winter Park History Museum
200 W New England Ave, Winter Park, FL 32789, United States
Admission: Free
Ph: +1 407-647-2330
Get directions

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Best place to eat nearby according to locals and visitors:
• Ruth’s Chris Steak House (4.7/5 stars, Steak, $$$)
• Santa Rosa Mexican Grill (4.6/5 stars, Mexican, $$)
• ANTONIO’S Maitland (4.6/5 stars, Italian, $$)

See the full list of places to eat near Winter Park History Museum.

The best hotel to stay near Winter Park History Museum based on overall price, location and amenities according to travelers:

The Alfond Inn at Rollins College (9.2/10 stars, $$$) – Booking.com

9. Enjoy the greenery at Mead Botanical Garden

Photo of visitors at Mead Botanical Garden | top things to do in winter park

Photo of visitors at Mead Botanical Garden | Mead Botanical Garden, Facebook

Mead Botanical Garden | Florida Hikes!, YouTube

Full of lush greenery, plants, and trees from all over the world, this garden is rich in beauty. Mead Botanical Garden is an oasis for all plants and wildlife. Each year, they host an annual orchid bloom that is both awe-inspiring and magical.

Whether you are trying to host an intimate gathering or looking for a scenic adventure, you will not regret your visit to the Mead Botanical Garden. Allow the gardens to take your breath away on the next visit.

Mead Botanical Garden
1300 S Denning Dr, Winter Park, FL 32789, United States
Admission: Free
Ph: +1 407-622-6323
Get directions

Best place to eat nearby according to locals and visitors:
• Keke’s Breakfast Cafe (4.5/5 stars, Breakfast, $$$)
• El Vic’s Kitchen (4.7/5 stars, Modern Indian, $$)
• Mee Thai (4.7 /5 stars, Thai, $$)

See the full list of places to eat near Mead Botanical Garden.

The best hotel to stay near Mead Botanical Garden based on overall price, location and amenities according to travelers:

Courtyard by Marriott Orlando Downtown (8.4/10 stars, $$$) – Booking.com

10. Set sail on a scenic boat tour

Winter Park Scenic Boat Tour | top things to do in winter park

Fun things to do in Winter Park, Scenic Boat Tour | Mike Whaling, Flickr

Scenic Boat Tour at Winter Park Florida | FloridaTVo, YouTube

Who doesn’t love an exciting boat tour? Climb aboard the 18-passenger pontoon boat and leave all your worries on the shore. For nature lovers and amateur photographers, any of the boat tours will putter through vistas of tropical trees, plants, flowers, and beautiful real estate. You will leave wanting to take another tour.

This excursion is an hour long tour, taking its visitors through the lakes surrounding Winter Park. There are tours every hour from 10 am to 4 pm.

Scenic Boat Tour
312 E Morse Blvd, Winter Park, FL 32789, United States
Admission: $14.00 for adults and $7.00 for children
Ph: +1 407-644-4056
Get directions

Best place to eat nearby according to locals and visitors:
• Park Avenue Pizza (4.6/5 stars, Pizza, $$$)
• Tabla Indian Restaurant Winter Park (4.7/5 stars, Indian, $$)
• Briarpatch Restaurant (4.5/5 stars, American, $$)

See the full list of places to eat near Scenic Boat Tour.

The best hotel to stay near Scenic Boat Tour based on overall price, location and amenities according to travelers:

Park Plaza Hotel (8.5/10 stars, $$$) – Booking.com

11. Discover the charm of Hannibal’s on the Square

Hannibal's on the Square settings on a Mother's Day celebration | top things to do in winter park

Hannibal’s on the Square settings on a Mother’s Day celebration | Hannibals lounge & Chez Vincent, Facebook

Hannibal’s on the Square is home to some of the best food and spectacular drinks. This historical neighborhood offers a quaint, enjoyable trip for all visitors. Hannibal’s on the Square will leave your appetite satisfied and your suitcase full. Looking for a great meal? Come here! Trying to find that perfect souvenir? This is the place!

Hannibal’s on the Square
511 W New England Ave, Winter Park, FL 32789, United States
Admission: Free
Ph: +1 407-599-2929
Get directions

Best place to eat nearby according to locals and visitors:
• Domu (4./5 stars, Ramen, $$$)
• Pig Floyds Urban Barbakoa (4.7/5 stars, Barbecue, $$)
• LaSpada’s Original Cheesesteaks & Hoagies (4.5/5 stars, Cheesesteak, $$)

See the full list of places to eat near Hannibal’s on the Square.

The best hotel to stay near Hannibal’s on the Square based on overall price, location and amenities according to travelers:

Homewood Suites by Hilton Orlando-Maitland (9.3/10 stars, $$$) – Booking.com

12. Explore the grounds of Rollins College

Students entering Rollins College campus entrance | top things to do in winter park

Students entering Rollins College campus entrance | Scott Cook, Flickr

I know what you’re thinking: who would want to visit a college on their vacation? Well, you just might after you find out what Rollins College has to offer. In 2011, this educational facility was dubbed one of the 50 Most Amazing College Campuses in The Best Colleges.

Within the walls of this Spanish-Mediterranean architecture, you will not only find beautiful gardens but history in its Walk of Fame and Cornell Fine Arts Museum.

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Rollins College
1000 Holt Ave, Winter Park, FL 32789, United States
Admission: Free
Ph: +1 407-646-2000
Get directions

Best place to eat nearby according to locals and visitors:
• Sakari Sushi (4.5/5 stars, Sushi, $$$)
• Francesco’s Ristorante & Pizzeria (4.7/5 stars, Southern Italian, $$)
• Choulala Fine Pastries (4.6/5 stars, Pastry, $$)

See the full list of places to eat near Rollins College.

The best hotel to stay near Rollins College based on overall price, location and amenities according to travelers:

The Alfond Inn at Rollins College (9.2/10 stars, $$$) – Booking.com

13. Take in the site at Dinky Dock Park

Photo of Dinky Dock Park | top things to do in winter park

Photo of Dinky Dock Park | Dinky Dock Park

Dinky Dock | Robbie Rockwell, YouTube

What once served as the Winter Park-Orland Railroad office now welcomes visitors from all around as a historical public park. Dinky Dock gives boaters access to Winter Park’s chain of lakes and sits directly on Lake Virginia, which is comprised of 220 acres of blue water. This site welcomes visitors with its historical appeal and fun lake activities.

Dinky Dock Park
410 Ollie Ave, Winter Park, FL 32789, United States
Ph: +1 407-599-3599
Get directions

Best place to eat nearby according to locals and visitors:
• Garp & Fuss (4.7/5 stars, Restaurant, $$$)
• Café de France (4.5/5 stars, French, $$)
• Boku Sushi & Grill (4.7/5 stars, Sushi, $$)

See the full list of places to eat near Dinky Dock Park.

The best hotel to stay near Dinky Dock Park based on overall price, location and amenities according to travelers:

Thurston House Bed & Breakfast ( 9.8/10 stars, $$$) – Booking.com

14. Casa Feliz Historic Home Museum

The beautiful Casa Feliz Historic Home Museum | top things to do in winter park

The beautiful Casa Feliz Historic Home Museum | Casa Feliz Historic Home Museum

This restored Spanish farmhouse is a dream come true! If you love architecture, you must visit this little piece of Europe located in Winter Park, Florida. Its beautiful landscape includes giant trees, courtyards, and rich greenery and is enough to impress any visitor. This is a great place to host a wedding or party.

Combined with this outstanding building with white-washed bricks and Spanish architecture, Casa Feliz Historic Home Museum makes for the perfect venue.

Casa Feliz Historic Home Museum
656 N Park Ave, Winter Park, FL 32789, United States
Admission: Free – $$
Ph: +1 407-628-8200
Get directions

Best place to eat nearby according to locals and visitors:
• Briarpatch Restaurant (4.5/5 stars, American, $$$)
• Prato (4.6/5 stars, Italian, $$)
• Rome’s Flavours (4.6/5 stars, Italian, $$)

See the full list of places to eat near Casa Feliz Historic Home Museum.

The best hotel to stay near Casa Feliz Historic Home Museum based on overall price, location and amenities according to travelers:

Residence Inn by Marriott Orlando Downtown (8.9/10 stars, $$$) – Booking.com

15. Laugh, play and ride at Disney World

Disney World | best things to do in winter park

Disney World | erin leigh mcconnell, Flickr

Disney World is one of the world’s best known amusement parks. It was first opened in 1971, and since then has offered wholesome, carefree entertainment for all ages. With over 45 different rides to choose from, you won’t have to ride the same roller coaster more than once (unless you want to!).

This amusement park is not just for families – whether you’re on a couples retreat or a girl’s weekend away, Disney World has something for everyone! Single day park passes start at just $109/person! Prices vary, depending on when and how long you plan to visit the park.

Disney World
Orlando, FL, United States
Admission: $109/person
Ph: +1 407-939-5277
Get directions

Best place to eat nearby according to locals and visitors:
• Gurgling Suitcase (4.8/5 stars, Bar & grill, $$$)
• Artist Point (4.5/5 stars, American, $$)
• La Luce (4.5/5 stars, Italian, $$)

See the full list of places to eat near Disney World.

The best hotel to stay near Disney World based on overall price, location and amenities according to travelers:

Four Seasons Resort Orlando at Walt Disney World® Resort (9.1/10 stars, $$$) – Booking.com


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