WinterPark City Tours delivers engaging lifestyle tours which showcase our community’s rich history, beautiful spaces and tomorrow’s possibilities.


Our passion is centered around making connections and watching the magic of introductions, spontaneous meetings and happen-stance collide in a synergy that no one could imagine possible. Let us be your resource for what you are looking for in our community. Just ask! If we cannot answer your question or provide a resource for you on the spot, be assured that we will make it our goal to respond in a timely and helpful manner. It will bless you, the residents, businesses and citizens of our Community. THAT folks, is our legacy!
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Tour Days and Times
Days: Thursday, Friday (am only) and Saturday
Times: 10:30am and 1:00pm
Where do the tours start?
All tours start at the Winter Park Welcome Center and Chamber of Comerce located at 151 W. Lyman Avenue in Winter Park.
What time do I meet our Tour Guide? Guests are encouraged to arrive 15 minutes prior to the tour departure time.
Tours will begin promptly and will last approximately 1 to 1.5 hours.
We suggest that you bring bottled water and wear sunscreen or hats to shield you from our brilliant sunshine. (Note: Tours go rain or shine.)
Can I wear high heels? You may, however we do not recommend it! Be prepared to walk along the sidewalks and cross brick streets that are often uneven. Walking shoes or sneakers are best. You'll want to dress comfortably for our Florida weather so be sure to bring a hat, sunscreen, and water. Leave the heels behind!
How can I reserve a spot on the Tour? You'll buy your ticket online in advance (at least 1 hour or more in advance). Tickets are sold on a first-come, first-served basis and tour size is kept to 30 persons.
What form of payment do you honor? Honestly, anything but cash or checks! You may buy as many tickets as you want, depending on availability, of course. If your group is larger than 10 adults or if you have a significant number of children or students, you may want to schedule your own private tour. We ask for two weeks notice to prepare for private tours.
Can I take photographs on the tour? Absolutely! And, if you do, please place the pictures liberally on your favorite social media site - Facebook, You Tube, Twitter, Linked In, etc...
Where do I park? There are public parking lots adjacent to the Welcome Center/Chamber of Commerce and street parking nearby. Be careful not to exceed the parking time limits or you may leave our friendly city with an unwanted ticket. Valet parking is also available at select locations on Park Avenue.