We're here to help
    Book online or call (650) 414-7338
    1. Local experiences/
    2. St. Augustine, FL/
    3. Land Activities/
    4. Guided Tours/
    5. Walking Guided History Tour of Old St. Augustine

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
    Greetwell

    Trusted by leading vacation properties and hotels, Greetwell helps travelers feel at home wherever they go. Enjoy curated experiences that carry you from the comfort of your stay into the heart of the local community.

    Safe & Secure Payments

    Guest Support

    • Help Center
    • (650) 414-7338
    • [email protected]

    Company

    • About
    • Nominate Providers
    • Hospitality Partners
    © 2025 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Gallery image
    Gallery image 2
    Gallery image 3
    Gallery image 4

    Walking Guided History Tour of Old St. Augustine

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

    From$25/ person

    Duration

    90 minutes

    Includes

    Guided walk, History commentary

    Highlights

    Start your day with a fully guided, 90-minute walk through the ancient streets of St. Augustine. Learn the complete history from the city's founding to the Gilded Age.

    • Explore the nation's oldest continuously occupied European settlement
    • Stroll the ancient streets with your guide
    • Learn the city's history from Spanish founding to Gilded Age
    • Enjoy an intimate, interactive small-group experience
    • Start early for a before-lunch experience

    What's Included

    • Guided walking tour
    • Historical commentary

    Things to know

    Suitable for ages 3 and up. Please arrive 10 minutes prior to start time to check in. Your guide will be wearing a purple shirt.

    Cancellation policy

    In the event of cancellation due to weather etc, by Spyglass Travel, guests will receive a full refund within 48 hours.

    Meeting location

    75 King St, St. Augustine, FL 32084, United States

    Perfect for

    • History buffs visiting Florida's oldest city
    • Families with kids wanting early morning activity
    • Small groups seeking intimate local knowledge
    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

    Reference #HUA5PK

    Adult

    $25

    Ages 13 - 55

    0

    Child

    $15

    Ages 3 - 12

    0

    Senior

    $20

    Ages 56+

    0

    Handpicked for you, so you can book with confidence

    • Best local prices

    • Flexible cancellation

    • Private and secure

    Each booking directly supports small businesses in our community.

    5.0 stars• 80 reviews

    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