10 Best Things To Do In Winter Park, Florida

Just north of Orlando’s major theme park attractions is a charming, Mediterranean-influenced town that people have been flocking to for over 100 years; so much so that it’s in the name—Winter Park. This Central Florida suburb is a preservation of Old Florida, mixed with European architecture and cultural influences. The college town is home to Rollins College, which is unmissable in its Mission Revival architecture. The academic institution sits at the end of a long walkable brick promenade, Park Avenue, where the locals gather to eat, drink, and greet each other.

Winter Park is kept shady and cool by ancient oaks and towering Cypress trees. It’s a verdant oasis just a short drive away from the bustling downtown of Orlando, and heavily trafficked Lake Buena Vista. Often overlooked by Orlando’s 70 million yearly visitors, Winter Park is well worth a break from the theme parks for a day or two of exploring its botanical gardens, dynamic culinary offerings, historic significance, and active arts scene.  

Things To Do

Hop Between Parks

No, we’re not talking about theme parks here. Winter Park is home to lush gardens and public parks. Enjoy the peace of a morning nature walk at Mead Botanical Garden, a forest of pine trees connected by boardwalks and specialty gardens. Enjoy yoga in the garden with the locals on Sunday morning, or come by and join avid local birders as they search for sitings. Next, wind your way through Winter Park’s residential neighborhoods to find the Kraft Azalea Gardens, a secret hideaway of prodigious Cypress trees, and a Grecian rotunda overlooking Lake Maitland. A popular picnic spot, plan your visit around golden hour when the sunset over the lake is magical. 

Harry P. Leu Gardens is a 50-acre tropical estate on Lake Rowena that is a must-visit. See the camellias in bloom in the winter, and azaleas in spring. Learn about Florida native cultivars and exotic tropical plants from the well-educated staff as you wander between greenhouses, trickling waterfalls, rose gardens, and bamboo forests. With its fertile gardens and walking trails overlooking the lake, it's a welcome and locally loved urban escape.

Cruise the Winter Park Chain of Lakes

Embark on a tranquil journey through Winter Park's Chain of Lakes, where Venetian-style canals sheltered in Spanish moss connect these bodies of water. The Winter Park Scenic Boat Tour offers a smooth pontoon excursion that includes narration from boat captains about Winter Park facts, history, famous residents, and the historic homes on the waterfront.

Alternatively, try a self-guided tour by renting a kayak and setting off on a leisurely paddle on these placid lakes that offer an up-close look at elegant waterfront estates and natural Florida wildlife, like the majestic Blue Heron.

Immerse Yourself in the Arts

Winter Park is home to several museums that make for enriching afternoon events. Explore the exhibits at the Charles Hosmer Morse Museum of American Art, home to the world's most comprehensive collection of works by stained glass artist, Louis Comfort Tiffany. Enjoy a stroll down Park Avenue as you make your way to your next stop—Rollins College Cornell Fine Arts Museum. This well-curated museum has a permanent collection of Old Masters, European works, and American art such as Andy Warhol and Tibor Pataky.

Artists looking to exercise their creativity should stop by Crealde School of Art, a multidisciplinary school that hosts workshops, classes, and rotating exhibitions that highlight Florida artists.

Tour Historic Homes & Architecture

Architecture enthusiasts will enjoy a guided tour of Casa Feliz Historic Home Museum. The Andalusian-style farmhouse is a notable work of James Gamble Rogers II and is the pillar to Winter Park’s Meditteranean architectural aesthetic. 

Czech sculptor Albin Poalasek retired to Winter Park after a prolific career. He continued sculpting in Winter Park at his waterfront home, which is now an interactive museum dedicated to his life and sculptures. The Albin Polasek Museum & Sculpture Gardens gives visitors a unique, intimate look at the 20th-century artist’s body of work, art studio, and inspirations.

Learn About Winter Park’s Beginnings

Of course, don’t leave Winter Park without learning about the city itself. Visit the Winter Park Historical Museum, housed in the old train station depot. It won’t take long to walk through the one-room museum, but you’ll leave knowing much more about this small town’s historic timeline—like why the peacock is on the city seal. Just three blocks west of this museum is the Hannibal Square Heritage Center, which houses photos and oral histories of Winter Park’s African American community.

Catch a Live Show

If engaging entertainment is what you crave then catch a theatrical performance at the historic Winter Park Playhouse, a year-round theatre that puts on productions with professional performers in an intimate setting. Music enthusiasts should check the calendar to see who’s playing at Blue Bamboo Center for the Arts, a jazz venue that showcases both local and international artists. Blue Bamboo frequently partners with Casa Feliz for atmospheric concerts at the historic home.

Places To Eat

Winter Park is where you’ll find some of Orlando’s most creative chefs and restaurants. Of Orlando’s four Michelin stars, one is located in Winter Park—Soseki, a 10-seat omakase experience. Even if you don’t make it to this fine dining experience, there are many other local eateries well worth a visit.

Sip on Craft Caffeine

On Saturday mornings, see what’s in season at the Winter Park Farmer’s Market held in Central Park across from the train station. Afterward, grab a craft coffee or matcha latte at New General Cafe while you stroll in and out of Park Avenue boutiques. For a bite, salivate at the counter of Croissant Gourmet, a Parisian-style boulangerie that’s perfect for a light lunch or classic French-style pastry to nibble on while you walk. Enjoy an atmospheric coffee date over long conversation and people-watching when you pick a table outside of Barnie’s Coffee & Tea Co., which boasts the best patio on the ‘Ave.

Dine on the Avenue

Much like Europe’s piazzas and promenades, Park Avenue is made for pedestrian exploration. Many long-standing and well-loved restaurants live on this street. Try the locally-owned Lale Turkish Cuisine. Wander down some of Park Avenue’s charming alleys and coves and you’ll find a few hidden restaurants that locals know to look for, like Atlantic Beer & Oyster, a small open-air establishment serving oysters on the half-shell with crisp beer or bubbly. 

Indulge in an elegant dinner at AVA MediterrAegean, which offers a front-row seat to Central Park’s Rose Garden in airy, lime-washed surroundings.

The Ravenous Pig has long been a mainstay in Winter Park and is to thank for introducing the community to farm-to-table dining. Dine inside on a seasonal-inspired menu, or relax outside at their casual beer garden while sipping a pint of their house-made beer and playing yard games.

Taste Something Different

For a more intimate experience, try snagging a reservation at Danilo’s Pasta Bar, a tasting menu with Italian, Filipino, and French influences. The 8-seat venue is located at East End Market, a European-style market and food hall. Upstairs is where you’ll find Danilo’s alongside The Neighbors, a sunny, midcentury-style bar and local artist gift shop. Come here for the best happy hour deals, Florida craft beers, and custom cocktails inspired by the spirit of Orlando’s unique neighborhoods. 

If you can’t make it to dinner at Danilo’s, then you just walk downstairs to Domu, a ramen restaurant that doesn’t take reservations but is well worth the wait. Put your name in and order a smokey-old fashioned from the bar to enjoy on the patio. Don’t forget to try a plate of crispy Japanese-style wings.

Places To Stay

Indulge in a luxurious stay at The Alfond Inn, Winter Park's premier boutique hotel located just blocks away from the dining and culture of Park Avenue. The Alfond offers a rare boutique experience in a city where large-scale resorts are the norm. Plus, the 4-star hotel helps fund scholarships to Rollins College students. The award-winning on-site restaurant, Hamilton's Kitchen, is also a great spot for a meal. 

Similarly, the Park Plaza Hotel also offers a boutique stay in Winter Park where guests can enjoy morning coffee and juice on the French-style terrace overlooking Park Avenue.