We're here to help
    Book online or call (650) 414-7338
    Ask AIAI
    Ask AIAI
    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

    Concierge Support

    • Help Center
    concierge@greetwell.com(650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Spyglass Travel

    Spyglass Travel

    5.0 • 80 reviews
    St. Augustine, FL

    Spyglass Travel is run by Kevin and Angie Rose, lifelong St. Augustine locals who have spent 30 years turning the city’s layered past into unforgettable adventures. Their award-winning walking tours, engaging field trips, and self...

    Report an issue

    Book Spyglass Travel

    Addon image

    St. Augustine Bootleggers, Brothels & Gambling

    Explore the hidden history of vice that shaped St. Augustine

    $33.75person
    Addon image

    St. Augustine History Tour: 90-Min Old Town Walk

    Discover the nation's oldest city on a small-group, 90-minute early walking tour

    From$28person

    Review summary

    5.0
    Excellent
    80 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