Explore Winter Park's History with the Peacocks, Presidents & Puzzles Tour
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Discover the charm of Winter Park, one of Florida’s best-kept secrets. Founded in 1887, this historic city boasts a rich past, including being the home of Florida’s first college and hosting multiple U.S. Presidents who chose its warm climate over Washington’s chill. It’s also a favorite spot for celebrities, making its streets filled with stories waiting to be uncovered.
Join us on the Peacocks, Presidents and Puzzles - The Winter Park Walking Tour to explore the beautiful brick-lined streets and learn about the fascinating history behind this vibrant community. Whether you’re a first-time visitor or a local looking to deepen your knowledge, this tour offers a lively mix of history, culture, and fun facts.
Over 1.5 hours, you’ll stroll through the heart of Winter Park, discovering its iconic spots and hearing stories about the influential figures connected to the city. It’s a perfect way to experience the city’s past and present in a relaxed, engaging setting.
Frequently asked questions
How long is the Winter Park walking tour?
The tour lasts approximately 1.5 hours, giving you plenty of time to enjoy the sights and stories.
Is the tour suitable for children and all abilities?
Yes! The tour is accessible for infants and small children in strollers, and all areas are wheelchair accessible. It’s designed to be enjoyable for everyone.
What’s included in the tour?
You’ll receive fun facts about local buildings, historical figures, and celebrity connections. Plus, enjoy a 10% discount on your next Orlando Tours adventure, earn Sunny Perks Reward Points, and participate in a 90-minute guided VIP tour of key Winter Park locations.
Can I cancel my booking?
Yes. You can cancel for a full refund at least 24 hours before the scheduled departure. Cancellations made within 24 hours are non-refundable.
Where do tours start?
Tours departing after 5:00 pm or on Sundays meet at the benches in front of the Winter Park City Administrative Building, located at 401 South Park Avenue.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1.5 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Fun facts about the buildings, historical figures, and celebrity connections to Winter Park.
- 10% discount for your next Orlando Tours adventure (valid for 30 days).
- Earn Sunny Perks Reward Points for gift cards or other discounts.
- 90 Minute Guided VIP Tour of Key Locations in Winter Park.
Not included
- Gratuities
Itinerary
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Stop 1
On this fascinating Winter Park history tour, you’ll learn why this picturesque village became (and still is!) a magnet for wealthy businessmen, politicians, celebrities, and their families. As you stroll along Park Avenue, lined with shops, restaurants, and historic buildings, we’ll share stories behind the walls and the personal histories that make Winter Park special.
Meeting point & pickup
Meet at the starting point
Tours which depart after 5:00 pm or on Sundays start from the benches in front of the Winter Park City Administrative Building, located at 401 South Park Avenue (southwest corner of South Park Avenue and West Lyman Avenue), Winter Park 32789.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day(s) before
- 0% refund if cancelled 0–1 day(s) before
Instant confirmation
Your booking is confirmed immediately after checkout.
From $42.00 per person
- Free cancellation
- Secure checkout with our booking partner
