If you think Central Florida is all theme parks and roller coasters, think again. Just north of Orlando sits Winter Park, a storybook town where brick-lined streets, mossy oaks, and a chain of sparkling lakes invite you to slow down and soak it all in.
Known for its elegant charm, lakeside beauty, and artsy soul, Winter Park is a refreshing blend of nature, culture, and classic Florida sunshine. It’s the kind of place where you can spend a morning paddling through canals, an afternoon browsing boutique shops and art museums, and an evening sipping wine on a patio lit by string lights.
What We Love
Scenic Boat Tours Through Hidden Canals
Hop aboard the famous Winter Park Scenic Boat Tour and glide past Spanish-moss-draped cypress trees, waterfront mansions, and secret garden views you can’t see from the street. It’s relaxing, breezy, and full of “I didn’t know this was here!” moments.
A Museum Filled With Tiffany Treasures
Art lovers, don’t miss the Charles Hosmer Morse Museum of American Art, home to the world’s most comprehensive collection of works by Louis Comfort Tiffany. Think stained glass windows, intricate lamps, and a chapel interior that will leave you speechless.
Park Avenue’s Boutique Magic
Stroll Park Avenue and you’ll feel like you’ve wandered into a European town square. Lined with indie bookstores, charming cafes, wine bars, and galleries, it’s a walkable paradise for people-watching and impulse shopping.
Rollins College Campus Strolls
Take a peaceful walk through the lakeside campus of Rollins College, where red tile roofs, palm-lined walkways, and sculpture gardens make every step feel like a scene from a romantic novel. You might even catch a free concert or community lecture.
Saturday Farmers’ Market
Held at Central Park’s edge, this cozy market is a local favorite. Think fresh flowers, handmade soaps, artisan cheeses, and live music under the trees. It’s the perfect place to start your weekend.
Atmosphere & Setting
Winter Park has a warm, polished vibe that feels both upscale and down-to-earth. The streets are lined with brick pavers and shaded by towering oaks, while the scent of fresh coffee and bakery treats drifts from sidewalk cafés. A train occasionally rumbles through town, adding just the right touch of nostalgia. You’ll hear soft jazz pouring from shopfronts, water lapping against boat docks, and friendly conversations echoing off sunlit patios.
Value (Is It Worth It?)
Absolutely. Many of Winter Park’s best experiences—like the lakeside walks, gardens, and architecture—are completely free. The boat tour runs around $16 per adult, and admission to the Morse Museum is just $6 (even less for seniors and students). Dining and shopping can be as indulgent or affordable as you like, and everything is close enough to fit into a single day. Perfect for couples, friend getaways, or anyone in need of a quiet recharge.
Other Considerations
Winter Park is walkable, but wear comfy shoes—brick streets and cobblestones can be tricky in heels. Parking is generally easy to find, especially in nearby garages. Summer afternoons can be steamy, so plan your outdoor activities for the morning or evening. Most spots are wheelchair accessible, and many shops are dog-friendly, too. If you’re visiting in spring, don’t miss the annual Winter Park Sidewalk Art Festival—it draws artists and visitors from across the country.
From lake breezes to Tiffany glass and hidden garden paths, Winter Park proves that Florida’s most memorable moments don’t always come with roller coasters. It’s a place to wander, linger, and fall just a little in love with the slower side of sunshine.
Winter Park
đ Brewer Ave, Winter Park, FL 32789