Wicked St. Augustine: Bootleggers, Brothels & Gambling Tour

The town that preached virtue while running vice

Wicked St. Augustine is a 90-minute guided walking tour through the nation's oldest city that uncovers the untold history of its thriving gambling, tavern and prostitution industries. The tour visits the courtyard of the old Alcazar Hotel (now the Lightner Museum) and the former Ponce de Leon Hotel (now Flagler College), along with the streets where private clubs, speak easies and boarding houses once operated. A live guide in English walks you through how political powers secretly supported these operations while maintaining a public image of religious virtue. Minimum age is 18.

Step-by-step itinerary

Stops and time spent at each2 stops

1. Lightner Museum10m
2. Flagler College10m

Explore St. Augustine's illicit history

• Visit Lightner Museum courtyard
• See old Ponce de Leon Hotel site
• Hear stories of private clubs and gambling
• Learn about speak easies and brothels

The experience

Ninety minutes walking through St. Augustine's downtown reveals a version of the nation's oldest city that never made it into the official histories. While the town marketed itself as founded on religious principles, it built its real wealth on taverns, gambling halls, and the sex trade. The tour stops at the courtyard in front of the Lightner Museum (the old Alcazar Hotel) and the grounds of Flagler College (the former Ponce de Leon Hotel), both landmarks of the Gilded Age luxury that gambling money helped finance.

The guide walks you through the streets where speak easies, private clubs and boarding houses, the period euphemism for brothels, operated openly while the city's political establishment looked the other way. You'll hear how prohibition was skirted, how the wealthy vacationers and working men of the city both fed these industries, and how the same officials who publicly condemned vice were quietly protecting the people running it. The tour is wheelchair accessible, and all areas and surfaces are level. Public transportation options are available nearby if you need them.

What’s included

• Guided narrative in English covering the illicit activities that built St. Augustine's economy.
• access to the courtyards and streets where gambling halls, speak easies and boarding houses once operated.

Information

Lasts 1h 30m, runs Tuesday, Thursday and Sunday at 19:30, from US$ 31.95 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesTuesday, Thursday and SundayDeparts at 19:30Last departure this season: 29 DecAnother day? ›

GroupUp to 26

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up to2h before

AgesAdult (18 and older) · Under 18: can't be booked

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

ConfirmationConfirmation within 48 h

Prices and times updated yesterday

Good to know

Low physical effortWheelchair accessibleAccessible transportStroller-friendlyPets welcomePublic transport nearby

Operated by Spyglass Tours

Is this one for you?This tour suits travelers 18 and older who want to understand the financial realities beneath St. Augustine's public image: the version of the city's founding that conventional tours skip. A small group walking tour with a live guide means you hear the stories as they happened on the actual streets where they unfolded, not as a summary from a distance.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What is the Lightner Museum and why does the tour start there?

The Lightner Museum occupies the old Alcazar Hotel, a landmark from St. Augustine's Gilded Age. The tour begins in its courtyard, which sits in full view of Flagler College (the former Ponce de Leon Hotel), allowing the guide to frame the wealth and decadence that gambling and illicit industries financed during that era.

Does the tour actually enter the Lightner Museum or Flagler College?

The tour visits the courtyard and exterior grounds of these landmarks rather than entering the buildings themselves. The focus is on the streets and locations where the gambling halls, speak easies and private clubs once operated.

What kind of stories will the guide tell about these locations?

The guide covers the gambling halls, speak easies and boarding houses that lined the streets, the upscale vacationers and working men who patronized them, and how the city's political powers secretly supported these operations while publicly maintaining a religious and family-friendly image.

Is this tour suitable for someone interested in St. Augustine's history but not specifically in its illicit past?

This tour focuses specifically on the unwritten history of gambling, taverns and prostitution, so it is designed for travelers who want to understand the financial and social realities that shaped the city rather than the conventional historical narrative.

How much walking is involved in the 90-minute tour?

The tour is a walking tour through downtown St. Augustine covering the streets and courtyards where these industries operated. It is suitable for all physical fitness levels and is fully wheelchair accessible.