Peacocks, Presidents, Puzzles – The Winter Park Walking Tour

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friends walking and shopping on park avenue in historic old world winter park during original orlando tours
Park avenue for shopping in historic old world winter park during the boat and shopping tour on original orlando tours

Tour Overview

Welcome to one of Florida’s best-kept secrets, the lovely city of Winter Park.

Chartered in 1887, Winter Park is more than 100 years old and has the pedigree to prove it. From being the location of the first Florida college to hosting multiple U.S. Presidents swapping the chills of Washington for a tropical paradise, Winter Park has a rich history just waiting to be explored and discovered!

On this fascinating Winter Park history tour, you’ll learn why this picturesque village became (and still is!) a mecca for wealthy businessmen, politicians, celebrities and their families over the years, as you wander along with the shops, restaurants, and historic buildings along Park Avenue, the thriving center of town. Wandering under the treed canopies and passing European-styled cafés, we’ll recount the personal stories of this Central Florida treasure and share the intriguing history behind the walls you see.

Whether you are a visitor or a seasoned Central Floridian, you encounter intriguing tales of the past, savor the present, and envision the future as we guide you through the incredible brick-lined streets of Winter Park!


Tour Includes:

  • 90 Minute – 2 Hour Guided Walking Tour Through Winter Park.
  • Stories from locals and insider tales.
  • Historical information about the surrounding area.
  • Fun facts about the buildings and historical figures in town.
  • Every person age 4 and above on the tour must have a ticket.
    • Adult Ticket: 13+
    • Child Ticket: 4-12
  • Please reserve in advance.
  • Confirmations will be sent within 48 hours of booking, subject to availability.
  • Tour must have at least two guests booked to operate.


The tour lasts approximately 90 minutes – 2 hours.

Tours which depart after 5:00pm and on Sundays originate from the benches in front of the City of Winter Park Administrative Building, located at 401 South Park Avenue (southwest corner of South Park Avenue and West Lyman Avenue), Winter Park 32789. History tours departing at all other times (i.e. before 5:00pm, Monday – Saturday) meet in the lobby of the Winter Park Chamber of Commerce Building, located at 151 W Lyman Avenue, Winter Park 32789. There is free parking near both buildings and along the local streets in the area. If coming from the I-Drive or Orlando tourist zones, you may want to allow at least 45 minutes travel time depending on your departure location; check your GPS, Waze, Google Maps or other apps so you can be sure to join our tour in plenty of time.

This tour operates on various days and times each month. Check the schedule on this page for exact details.

Please arrive 15 minutes before your scheduled tour to check in. There are no refunds or partial credits for guests who are late to the tour or no-shows. Tours depart rain or shine!

Private and Large Groups:

A private tour (ten or more) can be designed for your group to deliver a customized, extraordinary evening! For groups of ten or more, please contact Rich at or (407) 986-8687 to create your unforgettable visit!

Cancellation Policy:

You may receive a full or partial refund by notifying us via email at of the cancellation. No refunds shall be issued for cancellations not received at least 24 hours in advance of the starting time and date of your tour. Please review your Terms and Conditions document for other cancellation provisions.

Sunny’s Local Tips and Bits:

There are four towns named “Winter Park” in the United States. This one in Florida was the first. The other three are located in North Carolina, South Carolina and Colorado.


This historical walking tour is only offered in English. Florida weather varies throughout the year, so you may want to check the forecast and plan to dress accordingly. Tours operate rain or shine! We suggest wearing comfortable shoes and bringing an umbrella if there is a chance of rain. If using a tour voucher, reservation must be validated within 48 hours of tour departure time, or the reservation may be forfeited.


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100% of guests recommend

5 of 5 guest rating

based on 4 reviews

  • Angela McGaskin

    1 Review
    "Great time!"
    Me and my husband came out on the Peacock tour yesterday and had a great time! It was a perfect day for walking around and we learned so much interesting and fun facts, I would recommend this to everyone.
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  • "History Come Alive!"
    As a history buff, I've been on a few history tours in my day. They can often lean towards a stiff, "class lecture" tone. This tour did not fall into that. The guide did a great job at not just stating facts, but telling a story. We left having learned so much, and had a lot of fun in the process.
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  • Todd Bakers

    1 Review
    "Fun tour for my family"
    My family went on the peacocks presidents and puzzles tour last week and had a really good time. The tour was fun and the tour guide made the history fun and relatable for my younger children. Looking forward to doing the food tour next month!
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    Had a great time on a Winter Park walking tour today. Rich was very knowledgeable and entertaining. I would definitely recommend this tour company—very professional, friendly and helpful.
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