Things to Do in Winter Park, Florida

By VI | Disclosure: I use affiliate links

SR Productions/stock.adobe.com

Need a stylish, walkable escape with lakeside charm? I say head to Winter Park. Just north of Orlando, this town always charms me with its cobblestone streets, leafy canals, and seriously good café scene. I’ve spent afternoons boating, gallery hopping, and sipping espresso on sunny patios. Every time I go back, I find something new to love. You’ll feel the mix of small-town calm and artsy sophistication the moment you arrive.

Winter Park, FL Highlights

If you're adventurous like me: Take the Scenic Boat Tour – You’ll glide through canals and lakes, spotting elegant homes, giant cypress trees, and maybe even a heron or two. I’ve done it in every season—it never disappoints.
If you love history and art: Don’t miss the Charles Hosmer Morse Museum – I’ve marveled at the Tiffany glass more than once. The detail and color are unreal—you’ll walk out feeling inspired.
If you’re a shopper: Stroll Park Avenue – I always leave with a few too many bags. It’s lined with galleries, bookstores, and boutiques that feel handpicked just for you.
When I want to relax: I head to Central Park – I’ve had picnics under the oaks and even caught a live concert or two. You can just stroll and soak it all in—especially around the rose garden.
Got kids with you? Try Mead Botanical Garden – I’ve brought family here, and everyone—from toddlers to grandparents—enjoyed the trails, birds, and butterflies. You’ll love how peaceful it is.

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.