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History Comes Alive! Winter Park Walking Tour

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friends walking and shopping on park avenue in historic old world winter park during original orlando tours
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.

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:

  • Guided walking tour through Winter Park
  • Stories from locals and insider tales
  • Historical information about the surrounding area
  • Fun facts about the buildings and historical figures in town
  • 10% discount for your next Original Orlando Tours adventure (valid for 30 days)
  • Orlando discount booklet for each guest
  • Confirmation will be sent within 48 hours of booking, subject to availability
  • A minimum of 2 people per booking is required
  • The minimum age of all our guests is 6 years old

Exclusions and Extras:

  • Tour guide gratuity is not included in the booking price.

Season/Time:

Approximately 1.5 hours in total. This tour typically operates on Sunday mornings most months of the year.

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. Mr. Rogers met fellow music student and his future wife, Sara Joanne Byrd, on the campus of Rollins College in Winter Park.

Other:

This historical walking tour is only offered in English. Florida weather is unpredictable and may impact the tour. If the weather is deemed unsafe by our guide 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 group has left your departure point). This train tour also includes an Orlando discount savings booklet. We suggest wearing a hat, comfortable shoes and sunscreen to make your tour an enjoyable one in warm months as well as a jacket in cooler weather.

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Maximum number of people: 16
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