Step back into Winter Park’s rich history with a walking tour and scenic boat cruise past presidential estates and peacocks. Discover the stories behind Florida’s first college and elegant lakeside mansions.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; involves gentle walking and a relaxed boat ride
Wildlife
History
Winter Park was chartered in 1887 and became a cultural and educational center with Florida’s first college.
Conservation
Efforts are in place to protect Winter Park’s lake ecosystem and native plant species through community-led water quality programs.
Original Orlando Tours
Step back into Winter Park’s rich history with a walking tour and scenic boat cruise past presidential estates and peacocks. Discover the stories behind Florida’s first college and elegant lakeside mansions.
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 walking shoes
The initial walking portion covers historic streets with some uneven pavement. Good shoes help you stay comfortable.
Bring sun protection
Boat tours expose you to sun and breeze; wear a hat and sunscreen to stay comfortable on the water.
Stay hydrated
Carry water especially during warmer months to keep energy levels up through walking and boating.
Check boat accessibility
Confirm in advance if you require any mobility accommodations on the boat to ensure a smooth trip.
Comfortable walking shoes
Supportive shoes make walking on historic paved paths easier.
Sun hat
Protects against strong sun exposure during the boat tour.
summer
Light jacket or windbreaker
Wind can pick up on the water; a light layer offers comfort.
spring
Reusable water bottle
Staying hydrated is important on combined land and water tours.