“I could live here,” I thought, watching sunlight dapple the brick-lined streets of Park Avenue. There was something quietly magnetic about Winter Park — a blend of moss-draped trees, Mediterranean revival architecture, and an unhurried rhythm that made me slow down without trying. I came for the museums and gardens, but I stayed longer than planned, just because it felt good to linger.
Best Things to Do in Winter Park, FL
Park Avenue: Winter Park’s Walkable Heart
The hum of conversation spilled out from sidewalk cafés, and I found myself pacing slowly past boutiques and galleries without any rush to go inside. Park Avenue felt like a European main street dropped gently into Central Florida — shaded, polished, easy to love. I sat on a bench for a while with a cup of coffee and just people-watched. It was the kind of place that makes doing nothing feel like a plan.
Central Park: Pause Here First
Directly across from Park Avenue, Central Park stretches out like an open invitation. The fountains were bubbling, the grass tidy, and the oak trees generous with their shade. I wandered through the rose garden and paused by the sculpture near the fountain, feeling that early morning hush you only get before the kids start squealing near the splash pad. It was peaceful in a way that made me take a deeper breath than usual.
Marvel at Masterpieces at the Charles Hosmer Morse Museum of American Art
This museum is famous for its Louis Comfort Tiffany collection — and rightfully so. The rooms glow with iridescent glass, stained windows, and intricate lamps that feel almost holy in their craftsmanship. I lost track of time in the reconstructed Tiffany chapel, where the mosaics shimmered like they were breathing. I whispered to myself, “It’s like standing inside a jewel box.”
Stroll Through Art and Nature at the Albin Polasek Museum & Sculpture Gardens
Set along the shore of Lake Osceola, the Albin Polasek Museum offered a different kind of stillness. The sculptor’s former home, now a museum, feels lived-in and personal. The outdoor sculptures — some solemn, some whimsical — guide you along garden paths that hug the lake. I sat by one piece shaped like a gate, feeling like I’d stepped into a poem made of bronze and breeze.
If You Love Serene Escapes, Relax at Kraft Azalea Gardens
Hidden at the end of a residential street, Kraft Azalea Gardens is shaded and quiet, the kind of spot where you can hear the wings of birds. I walked under cypress trees and stood alone inside the Exedra monument, which felt strangely grand for such a tucked-away park. The lake was glassy, reflecting clouds that moved so slowly it was hard to tell they were moving at all.
Savor Spanish Flavors and Tapas at Bulla Gastrobar
When I walked into Bulla Gastrobar, the air was warm with the scent of garlic, olive oil, and something slow-roasted. I ordered the huevos Bulla — crispy potatoes, jamón, and a soft egg on top. When I cut into it, the yolk spilled golden over everything. It tasted smoky and rich, like comfort disguised as brunch. I sat by the window, watching Park Avenue blur by in soft motion, not ready to leave yet.
Wander Through Natural Beauty at Mead Botanical Garden
Mead felt wilder than Winter Park’s other green spaces — a mix of boardwalks, pine trees, and open meadows. I followed the trail past a butterfly garden and saw turtles basking on logs. It didn’t try to impress; it just offered space. I sat near the creek for a while and let the air move through me. It felt like pressing reset.
Step Into Historic Elegance at Casa Feliz Historic Home Museum
This blue-shuttered Spanish farmhouse is postcard-perfect, with thick walls and warm terra cotta tiles. Inside, I learned about architect James Gamble Rogers II, and outside, the arched loggia looked out over Central Park like a scene from another century. I imagined what it’d be like to live there, music echoing off the tile as citrus trees perfumed the yard.
If You Crave Contemporary Creativity, Explore the Rollins Museum of Art
Small but carefully curated, the Rollins Museum of Art sits on the edge of the Rollins College campus. I wandered through collections that spanned centuries and continents, but it was the quiet contemporary wing that stuck with me — color, shape, and shadow doing the work of language. A docent smiled as I stared too long at one piece. “It gets you,” she said. It did.
Bike or Stroll Scenic Paths on the Cady Way Trail
Part urban path, part nature corridor, the Cady Way Trail was where I stretched my legs and cleared my head. Bikers passed in a blur. I watched squirrels leap across live oak branches and felt the sun shift across my shoulders. It wasn’t a destination, really — just a way to connect things. But in that moment, it felt like the most important place of all.
Celebrate Community History at the Hannibal Square Heritage Center
I ended the day here, reading stories I hadn’t known, faces I hadn’t seen before. This small but powerful museum preserves the history of Winter Park’s African American community, and I left carrying their voices with me. The exhibits were filled with family photos, oral histories, and love stitched into fabric. “Everyone should have to stop here,” I thought.
Conclusion: A Place That Softens You
Winter Park didn’t ask for anything — not my urgency, not my productivity, not even my plan. It simply let me be. I arrived curious, and I left settled. This little town offered me art and nature, story and stillness. And in the end, I drove away slowly, like I might turn around and do it all again.
Winter Park At a Glance
- Drive time from Orlando: 20 minutes
- Vibe: Refined, walkable, artful, and green
- Best Time to Visit: Spring or early fall for cooler weather and blooming gardens
- Highlights: Park Avenue, Morse Museum, sculpture gardens, brunch at Bulla, lakeside quiet
- Facilities: Ample public parking, restrooms in parks and museums
- Cost: Many attractions are free or under $10
- Hours: Most attractions open 10am–5pm; parks open earlier
- Food Nearby: Park Avenue (Bulla, Briarpatch, Barnie’s Coffee), Hannibal Square
Best Time to Visit Winter Park, FL
October through April is my favorite window to visit. I’ve spent fall mornings walking Park Avenue with a breeze on my face, and spring afternoons surrounded by art festivals and blooming flowers. You’ll find it cooler, calmer, and perfect for outdoor dining or canal cruising.
How I Get to Winter Park (And How You Can Too):
- By Car: I just hop off I-4 and in about 15 minutes I’m sipping coffee on Park Avenue. You’ll be surprised how easy the drive is from downtown Orlando.
- By Train: I’ve taken Amtrak and SunRail into Winter Park Station—it’s right on Park Avenue, so you step out and you’re already in the heart of it.
- By Plane: I fly into Orlando International (MCO). From there, it’s about 25–30 minutes by car. You can rent one or grab a rideshare—I’ve done both, depending on the trip.
Where I Love to Stay (And Think You Will Too):
- The Alfond Inn – This is my go-to when I want something stylish and close to everything. The rooftop terrace and rotating art collection always make me feel like I’m on a special getaway.
- Park Plaza Hotel – I’ve stayed here for the cozy rooms and balconies. It’s got that old-world charm that makes you want to slow down. And yes, you’re right on Park Avenue.
- Nearby Orlando hotels – Sometimes I stay in Baldwin Park or Downtown Orlando for a different vibe. It’s still close, and you’ll have more options if you're planning a longer trip.
Jump to a Spot...
- • Marvel at Masterpieces at the Charles Hosmer Morse Museum of American Art
- • Stroll Through Art and Nature at the Albin Polasek Museum & Sculpture Gardens
- • If You Love Serene Escapes, Relax at Kraft Azalea Gardens
- • Savor Spanish Flavors and Tapas at Bulla Gastrobar
- • Wander Through Natural Beauty at Mead Botanical Garden
- • Step Into Historic Elegance at Casa Feliz Historic Home Museum
- • If You Crave Contemporary Creativity, Explore the Rollins Museum of Art
- • Bike or Stroll Scenic Paths on the Cady Way Trail
- • Celebrate Community History at the Hannibal Square Heritage Center