Old Town Trolley Tours: St. Augustine, with its nearly 500 years of history under Spanish, British, and U.S. rule, is packed with sights and attractions that both entertain and educate. For more than 30 years, Old Town Trolley has been offering tours that showcase the city's highlights.
The Old Jail: Constructed by Henry Flagler in 1891 and added to the National Registry of Historic Places in 1987, this Jail was in operation for over 60 years and could hold 72 prisoners at once.
Oldest Store Museum Experience: Our local actors and storytellers bring this tour to life with items and inventions from the turn of the century!
St. Augustine History Museum: A mix of historical exhibits and private collections showcases over 400 years of Florida's history.
St. Augustine Old Town Trolley Tours:
Relive the story of America’s first settlement as you explore the historic treasures of St. Augustine aboard the iconic Old Town Trolley. Your journey highlights centuries of adventure, exploration, and culture in the nation’s oldest continually inhabited city.
Top Historic Highlights:
Castillo de San Marcos: Step into the 17th-century Spanish fortress and uncover the stories behind its coquina walls.
Ponce de Leon’s Fountain of Youth: Visit the world-famous natural spring and even sample the legendary water for yourself.
Mission of Nombre de Dios: Explore the sacred grounds where the first Mass in America was celebrated.
Old St. Augustine Village: Stroll through authentic homes from the 18th and 19th centuries, offering a vivid look at early colonial life.
Along the route, the trolley also passes or stops at beloved local attractions including:
The Old Jail
St Augustine History Museum
Potter’s Wax MuseumThe Spanish Military Hospital
The Ximenez-Fatio House
The Gonzalez-Alvarez House — the oldest documented colonial home in Florida, lived in successively by Spanish, British, and American residents
You’ll even have the chance to tour the San Sebastian Winery and admire the beautiful campus of Flagler College, originally Henry Flagler’s magnificent Ponce de Leon Hotel.
There’s truly no better way to see all of St
St. Augustine Old Town Trolley Tours:
Relive the story of America’s first settlement as you explore the historic treasures of St. Augustine aboard the iconic Old Town Trolley. Your journey highlights centuries of adventure, exploration, and culture in the nation’s oldest continually inhabited city.
Top Historic Highlights:
Castillo de San Marcos: Step into the 17th-century Spanish fortress and uncover the stories behind its coquina walls.
Ponce de Leon’s Fountain of Youth: Visit the world-famous natural spring and even sample the legendary water for yourself.
Mission of Nombre de Dios: Explore the sacred grounds where the first Mass in America was celebrated.
Old St. Augustine Village: Stroll through authentic homes from the 18th and 19th centuries, offering a vivid look at early colonial life.
Along the route, the trolley also passes or stops at beloved local attractions including:
The Old Jail
St Augustine History Museum
Potter’s Wax MuseumThe Spanish Military Hospital
The Ximenez-Fatio House
The Gonzalez-Alvarez House — the oldest documented colonial home in Florida, lived in successively by Spanish, British, and American residents
You’ll even have the chance to tour the San Sebastian Winery and admire the beautiful campus of Flagler College, originally Henry Flagler’s magnificent Ponce de Leon Hotel.
There’s truly no better way to see all of St. Augustine’s iconic attractions. Just look for the charming orange and green trolleys—the best sightseeing experience in town!
FREE Self-Guided Walking Tours:
Continue your adventure at your own pace with complimentary self-guided audio walking tours. Using your smartphone, explore:
The Plaza de la Constitución
The scenic perimeter of Castillo de San Marcos
Hidden gems and lesser-known historical sites
As an added bonus, you can learn even more about the city’s heritage with the Visitors Bureau’s “Black History: People & Places” mobile app.
The Old Jail:
Discover one of St. Augustine’s most unique historic buildings on a guided tour led by in-character “jailers.” Step into:
The original cell blocks
The maximum-security areas
Displays of historic weapons
The gallows
The sheriff’s family quarters, located directly above the inmates’ cells
Learn how prisoners lived, how the sheriff’s family carried out daily life, and the role this imposing structure played in shaping the city’s past.
Oldest Store Museum Experience:
Travel back to the early 1900s and explore a re-created turn-of-the-century general store. Meet animated clerks, a butcher, and even a classic snake-oil salesman as they demonstrate:
Say hello to Mr. C.F. Hamblen, the store’s proprietor, and experience the charm and wonder of a bygone era.
St. Augustine History Museum:
Dive deeper into Florida’s rich past with exhibits featuring:
The influence of Henry Flagler, the visionary industrialist
Artifacts from Spanish and British rule
Unpublished photographs
More than 400 years of history, from early colonists to modern times
Replicas of Spanish galleons
Real treasure—gold, silver, and jewelry recovered from shipwrecks off the Florida coast
Located inside the Old Jail, the museum adds another fascinating layer to your St. Augustine experience.
