Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in St. Augustine…
    3. /Cultural Tours
    4. /Historical Tours
    5. /Red-Light District Walking Tour in St. Augustine
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Gallery image
    Gallery image 2
    Gallery image 3
    Gallery image 4

    Red-Light District Walking Tour in St. Augustine

    Trace West Augustine's hidden vice history with the author of Wicked St. Augustine

    5.0 stars• 92 reviews

    Duration

    1.5 hrs

    Includes

    Guided walking tour, historic sites

    Highlights

    Explore West Augustine's former "Country Club," where illegal liquor, gambling and prostitution shaped the city's past. Hear the author of Wicked St. Augustine reveal the stories behind its shadier history.

    • Discover the history of West Augustine's vice industry
    • Explore stories of illegal liquor, gambling and prostitution
    • Learn how local businesswomen served a city of nods and whispers
    • Uncover the lesser-known past behind familiar neighborhood locations

    Itinerary

    This is a typical itinerary for this product

    Stop At: Bog Brewing Company, 218 W King St, St. Augustine, FL 32084-4144

    Today a local brewery and pub, but its history is quite different. Your guide will divulge the shadier side of this locations history.

    Duration: 15 minutes

    Stop At: Leo C. Chase & Associate's Inc. Funeral Home, 262 W King St, St. Augustine, FL 32084, USA

    Today a thriving funeral home, but this was the center of the vice industry for years in the West Augustine area. The main location of the city's most famous, or infamous madam.

    Duration: 15 minutes

    Stop At: Sweet City Cupcakes, 233 W King St # A, St. Augustine, FL 32084, USA

    One of numerous stops along the way involved in notorious vice industries in St. Augustine's dark history.

    Duration: 15 minutes

    Stop At: Bog Brewing Company, 218 W King St, St. Augustine, FL 32084-4144

    Back to the beginnings, discovering several of the many notorious locations which make up the shadier side of the area of West Augustine. Enjoy the libations at this famous local pub after your tour as your guide recalls the area's hidden history.

    Duration: 15 minutes

    Important details

    • Arrive 10 minutes before your scheduled start time
    • Wear comfortable walking shoes for this outdoor tour
    • Plan for changing Florida weather

    Cancellation Policy

    Free cancellation up to 24 hours before start. Full refund if the operator cancels due to weather.

    Product ID: MC6XAY

    FAQs

    This is an outdoor walking tour.

    Wear comfortable walking shoes and plan for changing weather.

    Arrive 10 minutes before your scheduled start time.

    Meeting details

    BOG Brewing Co., 218 West King St, St. Augustine, FL

    Experience provided by Spyglass Travel

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Adult

    $33.75

    Ages 13 - 55

    0

    Senior

    $33.75

    Ages 56+

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    5.0
    Excellent
    92 reviews•Google Maps
    87
    0
    0
    0
    1

    Kevin clearly knows his stuff when it comes to St. Augustine history, and reviewers can't stop talking about how engaging he makes these tours. Multiple visitors mention he regularly goes over the allotted time because he's genuinely passionate about sharing the city's story, from Henry Flagler's influence on Florida to the architectural details that bring centuries past to life. His background as a paranormal investigator adds credibility to the ghost tours, which guests appreciate for being fact-based rather than gimmicky. Several reviews recommend booking early in your trip so you can use Kevin's insights to plan the rest of your visit. The personal touches stand out too. Kevin (who owns the company with his wife) is flexible with weather-related rescheduling, provides ponchos when needed, and even follows up after tours with additional historical context. The walking pace is described as slow and mobility-friendly. One reviewer mentions a tour with Angie that was equally delightful, though Kevin leads most experiences. Guests consistently say these walking tours beat the trolley alternatives for depth and completeness, making this a solid choice for anyone wanting to truly understand the oldest city in America.

    What people are saying

    Review 1 of 5
    5/5

    Kevin was a great guide. Very informative and not a tourist trap like most other haunted tours. Wait until you meet "Zoe".

    Photo of Craig Tedrow

    Craig Tedrow

    August 11, 2026

    Review 1 of 1
    5/5

    Kevin was a great guide. Very informative and not a tourist trap like most other haunted tours. Wait until you meet "Zoe".

    Photo of Craig Tedrow

    Craig Tedrow

    August 11, 2026

    Nearby activities

    Haunted History Ghost Tour in St. Augustine
    Ghost and Haunted

    Haunted History Ghost Tour in St. Augustine

    Hear real ghost stories with a paranormal investigator on a 90‑minute walk

    Hear real ghost stories with a paranormal investigator on a 90‑minute walk
    5.0 • 92 reviews
    $28/ person
    St. Augustine Historic District Walking History Tour
    Historical Tours

    St. Augustine Historic District Walking History Tour

    Walk St. Augustine’s historic district with a guide and audio equipment

    Walk St. Augustine’s historic district with a guide and audio equipment
    5.0 • 92 reviews
    $33/ person
    Secrets Walking Tour of St. Augustine
    Historical Tours

    Secrets Walking Tour of St. Augustine

    Discover overlooked stories, myths, and truths in historic St. Augustine

    Discover overlooked stories, myths, and truths in historic St. Augustine
    $33/ person
    St. Augustine Historic Horse-Drawn Carriage Tour
    Horse and Carriage Tours

    St. Augustine Historic Horse-Drawn Carriage Tour

    Explore St. Augustine’s history from a private horse-drawn carriage

    Explore St. Augustine’s history from a private horse-drawn carriage
    $186& up
    1-Hour St. Augustine Historical Electric Cart Tour
    Historical Tours

    1-Hour St. Augustine Historical Electric Cart Tour

    Ride an electric cart through St. Augustine’s top historic sites with a driver-guide

    Ride an electric cart through St. Augustine’s top historic sites with a driver-guide
    4.8 • 84 reviews
    $37/ person
    St. Augustine Haunted History Walking Tour
    Ghost and Haunted

    St. Augustine Haunted History Walking Tour

    Explore the darker stories and paranormal evidence behind St. Augustine's past

    Explore the darker stories and paranormal evidence behind St. Augustine's past
    $35/ person