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    Spyglass Travel

    Spyglass Travel

    5.0 • 1K reviews
    St. Augustine, FL

    Spyglass Travel & Tours is a locally owned guiding company that brings St. Augustine’s layered past to life for curious visitors. Founders Kevin and Angie Rose have spent three decades sharing their hometown, blending solid resear...

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    Book Spyglass Travel

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    St. Augustine Historic District Walking History Tour

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

    From$32person
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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

    From$33person
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    Walking History Tour in St. Augustine

    Walk St. Augustine’s historic district with a guide, from founding to the early 1900s

    From$28person
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    Haunted History Ghost Tour in St. Augustine

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

    From$28person
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    Explore St. Augustine's Vice History Walking Tour

    Walk St. Augustine’s hidden vice history with an author-guide

    $33.75person
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    Early Guided Walking History Tour in St. Augustine

    Walk Old St. Augustine with a guide and hear the city’s full story

    From$28person

    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