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Tours to Take in Winter Park

Winter Park Scenic Boat Tour

Nestled just outside of Orlando, Winter Park is a charming city brimming with natural beauty, culture, and hidden gems waiting to be explored. Whether you're a local looking to rediscover your backyard or a visitor searching for an authentic Central Florida experience, these standout tours offer a unique look at what makes Winter Park so special.

Original Orlando Tours

For those who want to explore Winter Park like a local, Original Orlando Tours is your go-to guide. Their curated experiences dive deep into the city’s rich history, arts scene, and culinary offerings. From walking food tours along Park Avenue to in-depth historical excursions including Mister Rogers, they strike a perfect balance between fun and informative. Guests rave about the guides’ insider knowledge and enthusiasm, making each tour feel like a personalized adventure through the heart of the city. For more information on Original Orlando Tours, click here.

Scenic Boat Tours

A true Winter Park staple, the Scenic Boat Tours offer a peaceful, picturesque journey through the city’s chain of lakes and canals. Departing from Lake Osceola, the one-hour narrated tour glides past opulent waterfront homes, tropical gardens, and historic landmarks. Guides share local lore and fascinating stories, adding depth to the stunning views. It’s an ideal way to see the natural side of Winter Park, especially on a sunny afternoon. For more information on Scenic Boat Tours, click here.

Albin Polasek Museum & Sculpture Gardens

Step into the world of renowned sculptor Albin Polasek at this beautifully preserved historic home and garden. The museum offers guided tours through Polasek’s former residence and studio, featuring many of his original works. Outside, the lush sculpture garden overlooking Lake Osceola is both serene and inspiring, dotted with over 50 sculptures. Visitors leave with a deeper appreciation for both the artist’s legacy and the artistry of the space itself. For more information on tours at Albin Polasek Museum, click here.

Rollins Museum of Art

Located on the Rollins College campus, the Rollins Museum of Art is a cultural gem that offers free admission and rotating exhibitions year-round. Tours here highlight an impressive collection spanning centuries and continents, from contemporary works to classical pieces. Docent-led tours provide engaging insights into the artwork and the stories behind them, perfect for art lovers and curious minds alike. It’s an inviting and enriching stop for anyone exploring Winter Park’s vibrant cultural scene. For more information on tours at Rollins Museum of Art, click here.

Casa Feliz

Casa Feliz, located in Winter Park, is a well-preserved historic house museum that offers visitors a glimpse into 1930s Spanish farmhouse architecture. The building, designed by acclaimed architect James Gamble Rogers II, showcases beautiful Mediterranean revival style with its red-tile roof, whitewashed walls, and wrought-iron details. Visitors appreciate the guided tours that provide insights into the house's history and architectural features. For more information on tours at Casa Feliz, click here.

Mead Botanical Garden

Mead Botanical Garden is a 47-acre urban oasis in Winter Park, open daily from 8 a.m. to dusk with free admission. Visitors can explore a variety of ecosystems, including a butterfly garden, boardwalk, creek, and wildlife-filled pond. Self-guided trails make it easy to discover native plants and animals at your own pace. As part of the Great Florida Birding Trail, it's also a popular spot for birdwatchers. Whether you're after a peaceful walk or a bit of nature education, it's a serene escape in the heart of the city. For more information on tours at the Mead Botanical Garden, click here.

Self-Guided Tours


Winter Park History Museum

Begin your journey at the Winter Park History Museum, located at 200 W. New England Avenue in the historic Farmers Market building. The museum offers rotating exhibits that delve into various aspects of Winter Park's past. After exploring the museum, pick up a free brochure for the self-guided walking tour, which features 20 historic sites throughout downtown Winter Park. For those looking to explore further, there are four additional sites on the north end of Park Avenue. This tour provides a comprehensive look at the city's rich history and architectural heritage. For more information on self-guided tours at the Winter Park History Museum, click here.

Charles Hosmer Morse Museum of American Art

The Charles Hosmer Morse Museum of American Art houses the world’s most comprehensive collection of works by Louis Comfort Tiffany, including his jewelry, pottery, paintings, art glass, leaded-glass lamps and windows, and his chapel interior from the 1893 World's Columbian Exposition in Chicago. The museum offers a self-guided audio tour that provides a sequential narrative through its galleries, beginning with the Laurelton Hall introductory gallery and concluding in the Tiffany Chapel. For more information on tours at Morse Museum, click here.

Rollins Mister Rogers' Neighborhood Walking Tour - Available in March

Experience the legacy of Fred Rogers on the self-guided Mister Rogers’ Neighborhood Walking Tour at Rollins College. Offered annually throughout March, Monday through Friday from 10 a.m. to 4 p.m., this free tour begins at the Olin Library, where visitors can view a collection of Rogers’ memorabilia, including his iconic sweater and sneakers, personal letters, and photographs. For more information on Mister Rogers' Neighborhood Walking Tour, click here

Whether you’re gliding across the lakes, strolling through art-filled gardens, or uncovering local history, Winter Park’s tours promise unforgettable experiences for every kind of explorer.