We now offer self-guided downloadable tours! See below!!!
Click the pic to book our Public Tour Experiences
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!
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.
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.
More experiences from Spyglass Travel
Wicked: Brothels, Bootleggers and Gambling in the oldest city
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Learn the history of the oldest city's oldest professions, vice. See how St. Augustine existed, prospered and thrived from this hidden history.
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided tours offer you the flexibility to experience your tour at your leisure. Learn how St. Augustine in Florida came to be the oldest colony in what is now the United States.
Self Guided Voicemap Tour: How Henry Flagler Created Florida
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
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.
Our Recommendations to enjoy our city...
Florida Republic Inshore Charters
Self Guided Voicemap Tour: How Henry Flagler Created Florida
Florida Water Tours: Scenic Boat Tours & Adventures!
We highly recommend our friends at Florida Republic Charters, who offer a variety of charters for any occasion. By offering a variety of fishing charters, they strive to ensure that you have the best experience exploring local St. Augustine waters.
Florida Water Tours: Scenic Boat Tours & Adventures!
Self Guided Voicemap Tour: How Henry Flagler Created Florida
Florida Water Tours: Scenic Boat Tours & Adventures!
Check out our friends offering popular Dolphin & Wildlife Adventure, Sunset Cruises, Wine Tasting Cruises, Private Charters and more.
Self Guided Voicemap Tour: How Henry Flagler Created Florida
Self Guided Voicemap Tour: How Henry Flagler Created Florida
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.
Book recommendations and other experiences!
Wicked St. Augustine by Ann Colby
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
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.
Walking The Way by Picasso Roberts
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
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.
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided Voicemap Tour: A Guide to St. Augustine's Colonial Period
Self-guided tours offer you the flexibility to experience your tour at your leisure. Learn how St. Augustine in Florida came to be the oldest colony in what is now the United States.
Kevin's Favorite Restaurants!
1. Pizzalley's Chianti Room
1. Pizzalley's Chianti Room
1. Pizzalley's Chianti Room
My favorite eatery in the city, hands down. Everything I've tried there has been wonderful, highly recommended!
2. Cap's on the Water
1. Pizzalley's Chianti Room
1. Pizzalley's Chianti Room
My date night go-to! Arrive just prior to sunset and watch the sun go down over the beautiful intracoastal waterway! Great food, great setting, great times!
3. Auggie's Draft Room
1. Pizzalley's Chianti Room
3. Auggie's Draft Room
Yes, Auggie's is a self-serve tap house. I'm sure the beer is great. But I quit drinking beer years ago, I include them here because they have the BEST CHEESEBURGER IN THE CITY!
Angie's Favorite Restaurants!
1. Prohibition Kitchen
2. St. Augustine Fish Camp
2. St. Augustine Fish Camp
Angie's favorite eatery in the city. The food, the drinks, the atmosphere, it really has it all for a restaurant offering in St. Augustine.
2. St. Augustine Fish Camp
2. St. Augustine Fish Camp
2. St. Augustine Fish Camp
Fish Camp’s interior is as fresh and inviting as the catch of the day, and the light from the sun shimmers off the water as a simple gift just before the sun sets.
3. Columbia Restaurant
2. St. Augustine Fish Camp
3. Columbia Restaurant
The best Cuban/Spanish food in the city. From the 1905 salad to the sangria, you will always remember your experience here!
Kevin's Book Recommendations! Flagler Era
Last Train to Paradise
Flagler: Rockefeller Partner and Florida Baron
Mr. Flagler's St. Augustine
Great read on the FEC railroad's extension from Miami to Key West, and excellent background information on Henry Flagler's transformation of Florida into the modern era!
Mr. Flagler's St. Augustine
Flagler: Rockefeller Partner and Florida Baron
Mr. Flagler's St. Augustine
Excellent dive into the story of Gilded Age St. Augustine's development and the daily operations of the magnificent Flagler hotels in the oldest city.
Flagler: Rockefeller Partner and Florida Baron
Flagler: Rockefeller Partner and Florida Baron
Flagler: Rockefeller Partner and Florida Baron
An in-depth examination of the economic effect of Henry Flagler and his construction of modern Florida, which is still felt to this very day! He is the father of Florida tourism and agriculture as well.
Kevin's Book Recommendations! Colonial Era
1491-by Charles Mann
St. Augustine: A Brief History
1491-by Charles Mann
To truly understand the Colonial Era, these two books by Charles Mann are a must read. Its a cumulative work detailing the times before, during and after the Columbian Exchange (arrival of Christopher Columbus).
1493-by Charles Mann
St. Augustine: A Brief History
1491-by Charles Mann
To truly understand the Colonial Era, these two books by Charles Mann are a must read. Its a cumulative work detailing the times before, during and after the Columbian Exchange (arrival of Christopher Columbus).
St. Augustine: A Brief History
St. Augustine: A Brief History
St. Augustine: A Brief History
More than just the colonial era. This book is a great overview of our city's history from the violence of the Spanish founding of the city through the birth of the vacation destination during the Gilded Age.
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!
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.
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.