Explore Fun and Frolic on St. Augustine's Naughty History Tours
- Terry Bastian
- May 12
- 3 min read
St. Augustine, Florida, is known for its beautiful beaches, historic sites, and vibrant culture. But did you know that it also has a cheeky side? If you are looking for a unique way to explore this charming city, the Naughty History Tours offer a delightful mix of fun and frolic. These tours take you on a journey through St. Augustine's past, revealing the risqué stories and scandalous events that shaped the city.
In this blog post, we will dive into what makes these tours so special, the fascinating tales you will hear, and why they are a must-do for anyone visiting St. Augustine.
What Are Naughty History Tours?
Naughty History Tours are guided experiences that focus on the more playful and scandalous aspects of St. Augustine's history. These tours are not your typical history lessons. Instead, they bring to life the stories of love, lust, and laughter that have unfolded in this historic city.
The guides are knowledgeable and entertaining, often sharing anecdotes that will make you chuckle or gasp. You will learn about the city's colorful past while enjoying a light-hearted atmosphere.
The Highlights of the Tour
1. Scandalous Stories
One of the main attractions of the Naughty History Tours is the scandalous stories. You will hear about the city's most notorious figures, including pirates, lovers, and even a few ghosts.
For example, did you know that St. Augustine was once home to a famous pirate named Sir Francis Drake? His escapades and romantic entanglements are just a few of the tales that will keep you entertained.
2. Historical Landmarks
As you stroll through the streets of St. Augustine, you will visit several historical landmarks. Each stop has its own story, often with a naughty twist.
The Castillo de San Marcos: This impressive fort has seen its share of battles and romantic rendezvous.
The Old Jail: Learn about the mischief that landed some of St. Augustine's residents behind bars.
These landmarks provide a backdrop for the stories, making the experience even more immersive.
3. Interactive Experience
Naughty History Tours are not just about listening to stories. They encourage participation and interaction. You might find yourself reenacting a scene or sharing your own funny anecdotes.
This interactive element makes the tour more engaging and memorable. You will leave with not just knowledge but also a smile on your face.
Who Should Join the Tour?
Naughty History Tours are perfect for a variety of audiences. Whether you are a history buff, a couple looking for a fun date night, or a group of friends wanting to explore St. Augustine in a unique way, this tour has something for everyone.
Families with older children can also enjoy the tour, as long as they are ready for some cheeky stories.
Tips for Your Tour
To make the most of your Naughty History Tour, consider these helpful tips:
Dress Comfortably: You will be walking, so wear comfortable shoes and clothing.
Stay Hydrated: Bring a water bottle, especially if you are visiting during the warmer months.
Be Open-Minded: The stories can be a bit risqué, so come with an open mind and a sense of humor.
Ask Questions: Your guide is there to share knowledge, so don’t hesitate to ask questions.
What to Expect After the Tour
After your Naughty History Tour, you will likely want to explore more of St. Augustine. Here are a few suggestions for what to do next:
Visit Local Restaurants: Enjoy a meal at one of the many local eateries. Many offer delicious seafood and Southern cuisine.
Explore the Nightlife: St. Augustine has a vibrant nightlife scene. Check out local bars and live music venues.
Take a Ghost Tour: If you enjoyed the spooky stories on your tour, consider joining a ghost tour to learn more about the city's haunted history.
Final Thoughts
St. Augustine's Naughty History Tours offer a unique and entertaining way to explore the city's past. With scandalous stories, historical landmarks, and an interactive experience, you are sure to have a memorable time.
Whether you are a local or a visitor, these tours provide a fresh perspective on St. Augustine's rich history. So, gather your friends or family, and get ready for a fun-filled adventure that will leave you laughing and learning.

As you embark on this journey through time, remember to embrace the fun and frolic that St. Augustine has to offer. You might just discover a side of history that you never knew existed.



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