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
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days).
  • Please reserve in advance.
  • Confirmations will be sent within 48 hours of booking, subject to availability.


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 Sarah 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.

Not Available
Tour type: Daily Tour
Duration: 3.25 Hours
Maximum number of people: Unlimited


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