Experience the highest rated walking experiences in St. Augustine!

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Spyglass Travel & Tours

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Book a Public Tour Experience Here, Today!

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10 am - (Our Earliest) Walking History Tour

Walking History Tour of St. Augustine's Historic District

Walking History Tour of St. Augustine's Historic District

A 90+ minute fully-guided Walking History Tour of St. Augustine's historic district. A perfect introduction to the city before lunch!

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Walking History Tour of St. Augustine's Historic District

Walking History Tour of St. Augustine's Historic District

Walking History Tour of St. Augustine's Historic District

2022 #11 Best of the Best (TripAdvisor) a 90+ min. fully guided experience of the nation's oldest city.  Experience the real history of the nation's oldest city.

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Haunted History Tour

Walking History Tour of St. Augustine's Historic District

Haunted History Tour

Visitors experience the real history of haunted locations with actual paranormal investigators.

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More experiences from Spyglass Travel

Wicked: Brothels, Bootleggers and Gambling in the oldest city

Wicked: Brothels, Bootleggers and Gambling in the oldest city

Wicked: Brothels, Bootleggers and Gambling in the oldest city

Learn the history of the oldest city's oldest professions, vice.  See how St. Augustine existed, prospered and thrived from this hidden history.

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Jules Art Tour: A Walking Art Tour of St. Augustine

Wicked: Brothels, Bootleggers and Gambling in the oldest city

Wicked: Brothels, Bootleggers and Gambling in the oldest city

Since Henry Flagler reinvented St. Augustine during the Gilded Age, it has been a home for artists and their works. Experience a customized guided tour of our city's artistic offerings.

For Booking Information
Hotel Ponce de Leon: Flagship of Henry Flagler's Hotel Empire

Self Guided Voicemap Tour: How Henry Flagler Created Florida

Wicked: Brothels, Bootleggers and Gambling in the oldest city

Self Guided Voicemap Tour: How Henry Flagler Created Florida

Self-guided tours offer you the flexibility to experience your tour at your leisure. Learn how sleepy St. Augustine helped transform Florida into a global vacation destination, because of one man, Henry Flagler.

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Recommendations from Spyglass Travel

Wicked St. Augustine by Ann Colby

COMING SOON-Scavenger Safari: The Great Lion Hunt of St. Augustine

Walking The Way by Picasso Roberts

Want to learn more about the wicked history of the nation's oldest city.  Click here to purchase a copy for yourself.

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Walking The Way by Picasso Roberts

COMING SOON-Scavenger Safari: The Great Lion Hunt of St. Augustine

Walking The Way by Picasso Roberts

Beyond our Haunted History Tour is a deeper experience through the medium Picasso.  Click here to experience her story by purchasing a copy, or contact her for medium services.

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COMING SOON-Scavenger Safari: The Great Lion Hunt of St. Augustine

COMING SOON-Scavenger Safari: The Great Lion Hunt of St. Augustine

COMING SOON-Scavenger Safari: The Great Lion Hunt of St. Augustine

Learn the history of the oldest city through the dangers of our Great Lion Hunt of St. Augustine.  Fun competition for groups, couple or individuals.

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Hello, friends!

My name is Kevin Rose and I am the co-owner of Spyglass Travel along with my wife Angie.  We founded this tour company with one thing in mind, create the best tour experiences for the visitors to our hometown, St. Augustine, Florida.  Won't you let us share our city with you?

St. Augustine Photo Gallery

    About Us

    Our Background

    My wife Angie and I have over thirty years experience in the tourism business in St. Augustine.  Our main point of that experience has been in the educational field trip arena, as well as public historical tours.  Angie is even a Black Powder Certified historical re-enactor for the Castillo de San Marcos, which means she gets to fire cannons!  Which is just as much fun as it sounds.  She always says "it's a blast!"

    How It all Started

    Don Juan Ponce de Leon was the first European to land in this area in 1513.  He claimed the land in the name of Spain, naming this the "land of flowers" or La Florida.

    Castillo de San Marcos

    The 'old fort' as it is lovingly referred to locally is the basis for St. Augustine being a historical vacation destination.  A key military structure from its completion in 1695 into the 20th century.  Come let us share the story of this magnificent structure.  

    School Field Trips

    The city of St. Augustine has played the most important role in the history of Florida.  From its founding by the Spanish in 1565, through the entire colonial period, the struggles of early statehood, the civil war and through the Flagler Era, no town in the state is more important to Florida History.  Allow us to make your field trip experience  the perfect combination of engagement, entertainment and education, creating memories your students will never forget! 

    For Field Trip information, email me here!

    The Flagler Era

    Named for gilded age industrialist Henry Flagler, this era was the key period in setting the tone for modern St. Augustine.  Experience these elegant, extravagant indulgences of the gilded age as it affected Florida forever.

    Haunted History Tour-click pic to book experience

    The city of St. Augustine lives up to being the most haunted city in America.  With human habitation dating back 6,000 years and European history stretching back into the 1500's, the haunting are heavy in this town.  From warfare, to disease, the reasons for haunting spirits in the city range across the spectrum.  Come investigate these entities with us.

    See the fabulous Flagler Memorial Presbyterian Church on your walking tour of St. Augustine.

    Walking History Tour-click pic to book experience

    Experience the history of the nation's oldest city in the most intimate way possible, a fully guided tour of the city.  A 90 minute in-depth experience you will never forget.

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