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    5. Explore St. Augustine Red-Light District Walking Tour
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    Explore St. Augustine Red-Light District Walking Tour

    Walk West Augustine’s Country Club and hear St. Augustine’s vice history

    5.0 stars• 1K reviews
    From$33/ personincl. taxes and fees

    Duration

    1.5

    Highlights

    Explore St. Augustine’s red-light district on a 1.5-hour walking tour led by the author of Wicked St. Augustine. Learn how illegal liquor, gambling, and prostitution shaped the city’s past around the famous Country Club.

    • Meet the author of Wicked St. Augustine for deeper local history
    • Walk in and around West Augustine’s famous Country Club
    • Discover how illegal liquor, gambling, and prostitution impacted the city
    • Learn about the women who worked in less-than-legal businesses
    • Start at BOG Brewing Co. at 218 West King St

    Things to know

    Arrive 10 minutes early. This is an outdoor walking tour, so wear comfortable walking shoes and plan for changing weather.

    Cancellation Policy

    Cancel at least 24 hours before the start time for a refund without penalty. Cancellation due to weather will result in a full refund.

    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

    Experience provided by Spyglass Travel
    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 (650) 414-7338

    Report an issue

    Reference #MC6XAY

    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
    1K reviews•Google Maps

    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

    Guide Kevin Rose delivered an insightful walking tour of St. Augustine on the occasion of my sister’s birthday. Along the route, Kevin peppered his meticulously researched content about St. Augustine, the oldest settlement in America, with humorous anecdotes and restaurant recommendations. He painted a colorful, detailed picture of St. Augustine with each stop, like charms on a souvenir bracelet. Henry Flagler’s “charm” would be the greatest of all, given that the Robber Baron built St. Augustine’s railroads, hotels, and churches. Kevin also unveiled the reasons for the Moorish influences on local architecture. Influences by the Spanish and Native Peoples received equal billing on this tour as well. He also honored our special request to learn more about St. Augustine’s seminal events surrounding the Civil Rights movement. I’ve been on many walking tours and Kevin’s was among the best! He was charming, kind, and knowledgeable—highly recommended Spyglass Tours!

    Photo of Sara Durkacs

    Sara Durkacs

    a year ago

    Review 1 of 1
    5/5

    Guide Kevin Rose delivered an insightful walking tour of St. Augustine on the occasion of my sister’s birthday. Along the route, Kevin peppered his meticulously researched content about St. Augustine, the oldest settlement in America, with humorous anecdotes and restaurant recommendations. He painted a colorful, detailed picture of St. Augustine with each stop, like charms on a souvenir bracelet. Henry Flagler’s “charm” would be the greatest of all, given that the Robber Baron built St. Augustine’s railroads, hotels, and churches. Kevin also unveiled the reasons for the Moorish influences on local architecture. Influences by the Spanish and Native Peoples received equal billing on this tour as well. He also honored our special request to learn more about St. Augustine’s seminal events surrounding the Civil Rights movement. I’ve been on many walking tours and Kevin’s was among the best! He was charming, kind, and knowledgeable—highly recommended Spyglass Tours!

    Photo of Sara Durkacs

    Sara Durkacs

    a year ago

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