St Augustine

St Augustine trip ideas

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Badge of ExcellenceSt Augustine, USA

Wicked St Augustine Bootleggers Brothels and Gambling in the Ancient City

1 hour 30 minutes
Mobile ticket
Offered in: English

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Overview

Whatever history you know of St. Augustine, this tour will teach you about the dark, unwritten side you might not know. The Ancient City has centuries worth of colonial era history and many more predating it, making it ripe for tales that are less than honorable. From the prostitution industry to the secret speakeasy taverns, you’ll learn about the seedy underbelly of St. Augustine’s past and which political powers allowed it to thrive.

A great experience for those who know the city’s traditional history well
See where underground gambling took place at illegal private clubs
Stroll down historic St. George Street
Pass by landmarks like Flagler College and the Lightner Museum

What's Included

Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'

Meeting and Pickup

Meeting point

Lightner Museum
75 King St, St. Augustine, FL 32084, USA
Guide will meet guests at the fountain in the front courtyard of the Lightner Museum in between the museum and Flagler College.

Start time

08:00 PM

End point

This activity ends back at the meeting point.

What To Expect

Lightner Museum

10 minutes • Admission Ticket Free

Flagler College

10 minutes • Admission Ticket Free

St. George Street

10 minutes • Admission Ticket Free

Plaza de la Constitucion

10 minutes • Admission Ticket Free

Additional Info

Confirmation will be received within 48 hours of booking, subject to availability
Wheelchair accessible
Stroller accessible
Service animals allowed
Near public transportation

Transportation is wheelchair accessible
Surfaces are wheelchair accessible
Most travelers can participate
This tour/activity will have a maximum of 26 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
Any changes made less than 24 hours before the experience’s start time will not be accepted.

Cut-off times are based on the experience’s local time.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

Reviews

5.0

73 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews

Reviews by Viator travelers.

We perform checks on reviews

Showing 1-10 of 73 reviews

Lots and lots of history

Meechelle_P, Apr 2024

It was a great experience. Ann had so much knowledge of the area and had done extensive research. The one note, she has so much to share and is so passionate about the history of St. Augustine, she can't do the tour in an hour and a half....it will go longer so be prepared, but well worth it.

Response from Host, Apr 2024

Yes, Ann is very passionate about her subject matter. She does run long, but always entertaining. Have a great time visiting.

Great Tour. Just Do it!

Melanie_H, Feb 2024

Great experience from an enthusiastic and knowledgeable guide. Things to know: the tour is 3 hours, not 1.5. Also, you only walk a total of a few blocks and sit for most of it. Recommend bringing a lightweight blanket if it's chilly outside. It was truly an EXCELLENT experience. Don't hesitate with this one.

Response from Host, Feb 2024

Ann will tour long, but she does tell you up front and will shorten if requested. Glad you had a great time, thank you for sharing your experience and thank you for the recommendation!

I loved it

Aubrey_H, Aug 2023

I actually ended up being the only person participating that night so I got a very personal tour! I’m a quiet, awkward person so I was anxious to hear this at first but Ann made me feel comfortable and kept me very engaged with her storytelling skills. It wasn’t what I expected from a tour but as someone very interested in history I was very pleased. I will point out that the length is much longer than advertised but she let me know offhand and mentioned that if I had time restrictions she could condense the tour/information. As I’m solo and had all the time in the world I went with the Real McCoy! (the origins of which you will learn from Ann in the tour.) There was lightening out and Ann made sure to keep an eye out for its distance and keep us near cover in case of rain. She also mentioned that she had cold water and bug spray available! It’s not like other walking tours where you’re moving around constantly — there were about 5 stops and at each you could find somewhere to sit/lean while Ann spoke. I really enjoyed my time and highly recommend to people who are interested in REAL history and not just what they will teach you in school. I ended up buying Ann’s book on kindle when I went home.

Response from Host, Aug 2023

So glad you enjoyed the experience. Yes, Ann takes great care with her tours and guests. She is a great storyteller and literally wrote the book on this subject matter. Thank you for sharing your experience.

Interesting and intriguing.

Michelle_S, Jul 2023

We had a lot of fun, she is very knowledgeable and will tell you things the other tours don't. Don't miss this one

Response from Host, Jul 2023

Yes! The darker side of St. Augustine's history is seldom discussed. Have a great visit!

Ann Colby's book, Wicked...

Erin_P, Jun 2023

Ann Colby's book, Wicked St Augustine was what led us to this tour. She is a wealth of knowledge on St Augustine, but the seedy bits are her specialty. She gives a very informative tour, sites her sources and this all leads to the tour lasting longer than advertised. The walking isn't very far, a few city blocks. I love history and the stories behind the community I'm visiting. This tour was worth every penny.

Response from Host, Jun 2023

So glad you enjoyed the experience. Ann is very passionate about the material and does a great job of story telling. Enjoy the rest of your time here in our city!

She was wonderful. Knew her stuff. If I was going to say anything negative, it was a little long,

Victoria_O, May 2023

The information about Henry Flagler. You don’t hear negative things about him too often in St. Augustine. We really like hearing the history good and bad.

Response from Host, May 2023

Mr. Flagler's legacy in St. Augustine is undeniable, but there will always be those who see it in a different light. Glad you enjoyed the experience, enjoy the rest of your visit.

Incredible tour

Kailey_A, Apr 2023

This was an amazing tour. SO INSIGHTFUL. Ann was incredible. She was so knowledgeable and was an excellent story teller. We were so engaged the entire time. Highly highly recommend if you love history and factual stories.

Response from Host, Apr 2023

We are so glad you enjoyed the experience. Ann is passionate about sharing this little known history of our city. Enjoy the rest of your time here and see you next time.

Excellent tour by...

Dennis_C, Apr 2023

Excellent tour by knowlegable guide that explored a lesser known aspect of St. Aug. I would certainly recommend to other visitors.

Response from Host, Apr 2023

Thank you for the kind words and taking the time to review. It is certainly an area of our history that is under-reported for sure! Have a great time here!

Wealth of Knowledge - Just Plan to Stay Awhile

Hannah_S, Mar 2023

What a wealth of knowledge Ann is! She knows so much and her passion is evident. Could have streamlined the presentation a bit for time’s sake (it’s closer to 3 hrs. than the stated 1.5h). Turns out Mr. Flagler is a real piece of work- was great to hear the real story!

Response from Host, Mar 2023

Glad you enjoyed the experience. There are always interpretations of Mr. Flagler, a complicated man. Have a great visit.

Enjoyable evening

Samuel_W, Feb 2023

The presenter, a charming local woman, seemed to know everything about the history of St Augustine. She had spent years researching and writing a book about the hidden seedy underbelly of the town, the financiers, the brothel culture, the moonshine industry and speak easies, etc. it is this knowledge that she shares on a 2-3 hour short walk around the core of the town. Mostly sitting with a few short walks between points of interest. It’s easy and entertaining.

Response from Host, Feb 2023

Glad you enjoyed the experience, Ann puts everything into her tour.

Ann made the wicked St. Augustine come to light.

Jamie_C, Feb 2023

Ann was excellent! She is a great storyteller, has done her research, and made the wicked passed St. Augustine come to light. We enjoyed our tour and would highly recommend it.

Response from Host, Feb 2023

There is always a history hidden in the shadows, Ann does a great job of shedding light on this often ignored history of our city.

Storyteller

Natasha_B, Jan 2023

Ann was great; visited this weekend, great tour very knowledgeable! Her book was also a great read- enjoyed photos to place to the characters throughout the journey.

Response from Host, Jan 2023

Thank you so much for taking time to share your thoughts. We are so happy you enjoyed the experience. She brings a side of history to life that is seldom revealed.

Wicked Indeed

Crystal_M, Jan 2023

Ann Colby was the most informative historic tour guide. Her knowledge and love for St Augustine's history was amazing. Our tour was supposed to 1.5 hours and we ended up spending almost 3 hours with Mrs. Colby. My husand I have been on several tours through out St Augustine. This was by far one of the best. The Wicked history of St Augustine was mind blowing.

Response from Host, Jan 2023

Glad you enjoyed the experience and thank you for sharing your review. She does a great job!

Interesting way to tour St. Augustine

Erin_G, Jan 2023

It was a long tour (longer than advertised) but the time went fast. Really interesting topic. I can’t attest to the accuracy, but it all seemed probable. Would highly recommend, especially if interested in the city’s history.

Response from Host, Jan 2023

Thank you for the kind words. We are pleased you enjoyed the experience and appreciate the recommendation. Have a great visit.

St Augustine and How it Really Was

Elizabeth_L, Dec 2022

This was an amazing tour. Ann Colby is wonderful as she unfolds the truths of early St Augustine. Learning about the brothels and how the “ladies” of St Augustine actually sustained this town and the contributions they made was a real eye opener to our past history. You’ll hear about the times of prohibition and how St Augustine thrived despite what was going on elsewhere in this country at that time. This is a tour you will not want to miss if you really love history.

Response from Host, Dec 2022

Ann does a great job of shining a light on a hidden part of our city's history. So glad you enjoyed the experience. Have a great visit!

Hidden history revealed!

Carolyn_C, Aug 2022

This tour was fantastic! The tour guide has done an incredible amount of research on the history of St. Augustine and brought that history life. The stories she told were fascinating. There was no point during our 2+ hours together that anyone in my group felt bored. If we had had more time, we could have listed to the tour guide into the wee hours of the night!

Response from Host, Aug 2022

So glad you enjoyed the experience. Ann has done an incredible job of researching her tour. We appreciate the time you took to share your review.

Take this tour you won’t regret it!!!

Stephanie_D, Aug 2022

Wow! We got soooo much more than we bargained for. She spent extra time with us and answered all our questions. She is well researched and definitely engaging! She provides extra information than what was in her book. A truly delightful experience and we will definitely be returning customers.

Response from Host, Aug 2022

Awesome! We are so glad you enjoyed the experience. Ann is very passionate about the subject matter, and it shows.

Interesting - But Targeted for the Political Activist with a "Flexible" Regard for Historical Authenticity

James_T, Jun 2022

Nice tour guide with interesting stories, but some of her details were historically inaccurate. Also, her presentation was a little too political: I felt like I was sitting in a Feminist Studies lecture (i.e., men bad, women enslaved and degraded by men from 1565 through 1970s).

Response from Host, Jul 2022

So sorry you were a bit disappointed with the experience. The author, also the guide, has painstakingly researched the subject. Thank you for taking the time to review this tour, it helps us be better in the future. Have a great rest of your experience here in our city.

A St. Augustine MUST - D0!!

Dana_G, Apr 2022

Our guide- Ann Colby- was fantastic! She was a treasure trove of historical facts and presented them in a vibrant manner that brought the past to life. We were spellbound and could have listened to her forever. She presented us with a St. Augustine that we would never have discovered on an ordinary tour: meticulously researched info - sometimes bawdy and outrageous, always startling and fascinating. Also...we recommend buying her book: now used as a text in college curricula, and chock full of delightful facts!

Response from Host, Apr 2022

We are so glad you enjoyed the experience. Ann does a fantastic job of bringing this darker side of our history, out of the shadows and into the light. Thanks for taking the time to spread the word!

Wickedly Fun

Erin_M, Mar 2022

Our guide was very knowledgeable and passionate. It was great to hear such interesting information to kick off our trip to St. Augustine.

Response from Host, Mar 2022

We agree, Blanche is something special. Thank you for kind words. Have a great rest of your vacation.

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