Discover the rich history of Winter Park, Florida on a walking tour. Explore the charming streets, beautiful lakes, and stunning mansions while learning about the town’s famous visitors and historic landmarks.
Discover the rich history of Winter Park, Florida on a walking tour. Explore the charming streets, beautiful lakes, and stunning mansions while learning about the town’s famous visitors and historic landmarks.
- Winter Park - 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…
- Winter Park - 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.

- 90-minute guided VIP tour of Winter Park’s key locations.
- Travel through lakes and canals to see splendid mansions.
- Learn fun facts about historical buildings, figures, and celebrities.
- 10% discount on your next tour with Original Orlando Tours.
- Earn rewards with Sunny Perks for gift cards and discounts.
- 90-minute guided VIP tour of Winter Park’s key locations.
- Travel through lakes and canals to see splendid mansions.
- Learn fun facts about historical buildings, figures, and celebrities.
- 10% discount on your next tour with Original Orlando Tours.
- Earn rewards with Sunny Perks for gift cards and discounts.
- Gratuities
- Gratuities
Welcome to Winter Park, a hidden gem in the sunshine state of Florida!
Founded in 1887, Winter Park boasts a history that spans over a century. It is renowned for hosting Florida’s first college and has been a preferred holiday spot for various U.S. Presidents who traded Washington’s cold climate for a tropical haven. The town has been a magnet for…
Welcome to Winter Park, a hidden gem in the sunshine state of Florida!
Founded in 1887, Winter Park boasts a history that spans over a century. It is renowned for hosting Florida’s first college and has been a preferred holiday spot for various U.S. Presidents who traded Washington’s cold climate for a tropical haven. The town has been a magnet for numerous famous personalities, revealing an intriguing history ready to be unmasked!
This sightseeing excursion offers you a glimpse of Winter Park from both the city streets and the charming lakes and waterways that envelop this historical town. Your guide will walk you through the fascinating past of this southern holiday town and the prominent celebrities who’ve made their mark here.
Enjoy breathtaking views of the majestic mansions of previous and present town influencers, as well as the natural wildlife that inhabit Winter Park and its enchanting aquatic landscapes.
Whether you’re a tourist or a long-time resident of Central Florida, this tour is sure to provide an enjoyable and educational experience as you delve into the rich history of this picturesque hamlet!
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.