Historic Winter Park Florida Supervisit

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Tour Overview

Founded as a resort community by northern business magnates in the late 19th and early 20th centuries, Winter Park today, with its cafes and mansions, blends a touch of continental Europe with old Southern elegance. Original Orlando Tours will rescue you from the crowds of the tourist zone for a visit to this beautiful suburban Orlando hamlet that U.S. President Chester Arthur once declared “the prettiest place I have seen in Florida”.

This tour looks at the history and present-day scenery of Winter Park and begins thus with a visit to the Winter Park History Museum for an overview of the past and a preview of the rest of our visit.

Then we’re off to see the sites of Winter Park. Our walk through the town is a voyage into the history of a haven for northern elites and the local families that supported them, to places that inspired the legendary Fred Rogers to create his Neighborhood of Make Believe.

Finally, we’ll hop on a pontoon for a boat tour to explore the narrow, hidden canals of Winter Park on our way to the multi-million-dollar mansions of some of Winter Park’s wealthiest residents. At the end of the tour there is time to shop and dine on historic Park Avenue, a quaint high street full of boutiques and cafes in the heart of town, to wrap up your day away to this iconic village!

This tour is subject to availability and will be followed up for confirmation upon booking.

Historic Winter Park Florida Supervisit Tour Includes:

  • Round-trip transportation from your hotel
  • Parking and admission to the Winter Park History Museum
  • Guided walking tour of Winter Park including Fred Rogers sites
  • Admission ticket for a one-hour boat tour of Winter Park
  • Shopping/dining time on Park Avenue
  • Assortment of cold drinks on the journey
  • Professional guide with local commentary
  • This Original Orlando Tours Explorer Tour includes an Orlando discount booklet for each guest
  • Confirmation will be sent within 48 hours of booking, subject to availability
  • A minimum of 4 people per booking is required
    • Children Ticket: 4-12
    • Adult Ticket: 13+
  • The minimum age of all our guests is 4 years old

Exclusions and Extras:

UPGRADE your tour to include lunch for an additional $20+tax/person (tour length increase of one hour)

This tour is not wheelchair accessible


Approximately 4 hours total. Please note that Orlando traffic conditions can vary widely while I-4 is under construction. This tour typically operates all year, Tuesday – Saturday.

Cancellation Policy:

You may receive a full or partial refund by notifying us via email at info@originalorlando.com of the cancellation. No refunds shall be issued for cancellations not received at least 72 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:

The world famous “Temple” orange was discovered in Winter Park and developed in the surrounding groves. The original tree still stands on private property within the city. Fred Rogers met fellow music student and his future wife, Sara Joanne Byrd, on the campus of Rollins College in Winter Park. Book your tour on a Saturday and visit the Winter Park Farmer’s Market, a popular community gathering place that provides fine produce, plants, baked goods and so much more. A boat tour has operated in Winter Park for over 100 years.


This tour is only offered in English. Florida weather is unpredictable and may impact the tour. If the tour boats are closed, a visit to the Albert Polasek Museum or other activity may be substituted. If our guide deems weather conditions for this tour potentially unsafe due to weather conditions prior to commencement of the tour, Original Orlando Tours will offer a substitute tour at the original day and time, offer a credit to be used on any future Original Orlando Tours adventure, or fully refund the tour fee, the choice of which is at the option of our special guests impacted by the weather disruption. There are no refunds once the tour has commenced (i.e., the vehicle has left your departure point). This tour also includes an Orlando discount savings booklet. Please note: This is largely a walking tour once we get to Winter Park. We suggest wearing a hat, comfortable shoes and sunscreen, especially for the boat tour, to make your visit an enjoyable one in warm months as well as a jacket in cooler weather.

Not Available
Tour Type: Daily Tour
Duration: 4 Hours (5 Hours with Upgrade)
Maximum number of people: 12


100% of guests recommend

4.9 of 5 guest rating

based on 4 reviews

  • "Incredible!"
    Such a pretty little town. Shops were amazing. I recommend getting the lunch upgrade the food was delicious
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  • Patty Verinica

    1 Review
    "Very interesting!"
    I need to first say that in all my visits to Orlando, I had never been out of the park area, which I'm so bummed about. So we did a tour with this company and Dan (crazy blue hat, remember??!) to a secluded beach. It was beyond my expectations, so we booked another one to Winter Park with Sarah, and had a blast. I never new Mr. Rogers was so tied to Orlando (well Winter Park) and it was so cool to see the "inspiration inscription" as Sarah called it and know that's what started it all for him. Boat tour was good. Lots of big mansions. Had a nice lunch too. Already booked the Sanford tour, but wish I had traveled with these people sooner as I had no idea there was so much other stuff in Orlando to do. Ya'll have fan for life now though! 🙂
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  • candice from Reno

    2 reviews
    "Great day away from the crowds"
    Really enjoyed our visit. Interesting history, fun tour guide.
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  • Lil Feinholdt

    1 Review
    "Loved it!!"
    I got my picture taken in front of this Mr. Rogers portrait, but don’t see how to upload it. Anyway, I loved the tour and Dan and his facts and humor! I will be sending lots of Feinholdts your way in the future!!
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