

Discover the nation's oldest city on a small-group, 90-minute early walking tour
90 minutes
Guided walk, History commentary
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.
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.
In the event of cancellation due to weather etc, by Spyglass Travel, guests will receive a full refund within 48 hours.
75 King St, St. Augustine, FL 32084, United States
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.
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!
Sara Durkacs
a year ago
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!
Sara Durkacs
a year ago