THIS Is Winter Park

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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

Want to catch the best highlights of Winter Park on an afternoon? We have you covered with our THIS is Winter Park tour – a half day walking tour of the top spots is this beautiful Central Florida village with European style!

You learn why this was Central Florida’s original tourist destination as you visit sites that date back to the founding of the town; learn about (or maybe even spot!) celebrities past and present who are attached to Winter Park and their favorite hangouts; sample delicious local flavors at an old-fashioned tasting room; and then enjoy a full included lunch on world famous Park Avenue.

You finish your day cruising the lakes and canals of Winter Park as you admire the beautiful junctures of where breath-taking mansions and Florida wildlife come together, the perfectly relaxing way to cap off your Winter Park adventure.

Tour Includes:

  • 4 Hour Guided Tour Through Winter Park.
  • History/Celebrity Walking Tour of Winter Park.
  • Visit to a tasting room with food samples.
  • Full lunch service.
  • One-hour boat tour of the Winter Park lakes and canals.
  • 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.


The tour lasts approximately 4 Hours.

Tours depart meet in the lobby of the Winter Park Chamber of Commerce Building, located at 151 W Lyman Avenue, Winter Park 32789. Due to COVID-19 the lobby may be closed. If the lobby is closed, your guide will meet you outside of the lobby. There is free parking near the departure point 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.


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