Peacocks, Presidents and Puzzles + Boat Tour

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historic old world winter park boat tour
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.

You’ll also enjoy a boat cruise on the Winter Park Scenic Boat Cruises as part of your visit where you’ll see awe-inspiring mansions and estates of past and current business leaders and celebrities.

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.
  • 1 Hour Boat Cruise Along the Canals and Lakes of Winter Park.
  • Stories from locals and insider tales.
  • Historical information about the surrounding area.
  • Fun facts about the buildings and historical figures in town.
  • Travel the lakes and canals of Winter Park to view magnificent mansions and local sites.
  • Every person age 2 and above on the tour must have a ticket. Children 6 and under must wear a life jacket on the boat.
    • Adult Ticket: 13+
    • Child Ticket: 4-12
    • Infant Ticket: 2-3
  • 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 3 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.


100% of guests recommend

5 of 5 guest rating

based on 3 reviews

  • Karen Crossman, Iverheath, UK

    1 Review
    "Quite a Nice Tour!"
    This is a perfect tour to learn about a fascinating Orlando suburb that looks like it should be in Southern Europe! Michael and Dan gave us a very informative walk through the town's founding. Some of the things they talked about were too far to walk to, but then we finished with the boat ride where we able to see those sites from the water. The boat is like a pontoon and is very smooth. Michael and Dan gave us cold waters to take on the boat too which was well appreciated. Overall this was really a nice day out at a good value.
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  • Garrett Tomlin

    1 Review
    "History by Land and Sea"
    Really enjoyed learning the interesting story of Winter Park with our guides and then packaging it up with a tour on the boat. The guides ended the tour at the docks so everything was seamless. Enjoyed it chaps!
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  • Samantha Morrison, Oviedo, FL

    1 Review
    "Great Way to Get Back Out Again!"
    Got my second shot and just wanted to get out, but not a huge crowd and this was just what I needed. Only 8 in our group plus us. Guides were super friendly and knew their stuff. The walk is really well planned out because all the stops are in the shade with benches. Not a ridiculous amount of walking, and the guides tell stories along the way. The first part of the tour ends at the boat docks where the guides walk you to your seating area and provided us cold bottled water (the boat doesn't have a canopy so that was more appreciated later than we knew at the time). I enjoyed seeing things on the boat that the guides had talked about so it all kind of came together for me. I do very much recommend this tour for a relaxing day out.
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