Discover Fred Rogers’ Winter Park through a heartwarming walking and boat tour by Original Orlando Tours. Walk the spots where his love story began, then cruise past stately estates on scenic lakes.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
3–4 hours
Fitness Level
Participants should be comfortable walking on flat, paved surfaces for about 1.5 hours and able to remain on a boat for 1.5 hours.
Wildlife
History
Winter Park developed around a chain of lakes and served as a retreat for wealthy gardeners and business leaders in the early 20th century.
Conservation
Efforts to maintain water quality in the lakes protect the delicate habitats supporting local wildlife visible from the boat tour.
Original Orlando Tours
Discover Fred Rogers’ Winter Park through a heartwarming walking and boat tour by Original Orlando Tours. Walk the spots where his love story began, then cruise past stately estates on scenic lakes.
Original Orlando Tours is a guided-tour company based in Orlando, FL, that offers curated walking and boat experiences across International Drive, ICON Park, and Winter Park. The company operates a range of themed tours including food-focused walks such as Flavors of ICON Park and Flavors of Winter Park, arts and culture tours visiting local museums, history-focused walks like Peacocks, Presidents, and Puzzles, family-friendly Mister Rogers walking tours, and evening ghost walks that explore Winter Park’s haunted past. Several experiences combine a guided walking component with an optional scenic boat cruise showcasing Winter Park’s lakeside mansions.
Tours are led by local VIP guides and knowledgeable storytellers who highlight culinary partners, museum stops, historic landmarks, and notable estates, providing context and recommendations. Sample menus and restaurant discounts are included on food tours, and museum visits are part of arts-focused itineraries. All experiences emphasize accurate local history, curated partner venues, and accessible routes through popular Orlando and Winter Park neighborhoods.
Original Orlando Tours markets a mix of culinary, historical, arts, and pop-culture themes to appeal to visitors seeking immersive, walkable experiences in Central Florida. The business operates within Orlando and Winter Park and offers options suitable for day visitors, couples, families, and groups interested in food, architecture, or local lore. Reviews and local listings can confirm tour availability, schedules, and booking details. Booking is available online and through local visitor centers; schedules vary seasonally and reservations are recommended for popular tours to secure preferred dates and guarantee spots for groups and individuals year-round.
Tours Offered
10
Walking and boat tour experiences
Base Location
Orlando, FL
Operating in Orlando and Winter Park
Themes
Food · History · Arts · Ghosts
Specialized themed experiences
Guides
VIP & local guides
Local experts and storytellers
Book a walking or boat tour in Orlando and Winter Park today — check availability and secure a spot online.
Wear comfortable shoes
The walking portion covers several blocks on paved terrain, so supportive shoes help maintain comfort throughout the tour.
Bring a water bottle
Carry water to stay hydrated, especially during warmer months when Florida’s humidity spikes.
Check the weather forecast
Tours take place rain or shine, so pack a light rain jacket or umbrella if needed.
Arrive early
Plan to reach the meeting point at least 10 minutes before departure to ensure a smooth check-in.
Comfortable walking shoes
Supportive footwear ensures comfort during city walking sections.
Sun protection (hat, sunscreen)
Florida sun can be strong even in mild weather; protect your skin on open sections.
spring
Reusable water bottle
Bring water to stay hydrated in warm and humid conditions.
summer
Light rain jacket
Summer thunderstorms are common; a rain jacket helps keep you dry without bulk.
summer