St. Augustine, America’s oldest city, is rich with beautiful architecture and attractions. Take your time seeing everything the gorgeous city has to offer with this St. Augustine trolley tour. Your Old Town Trolley tour gives you unlimited hop-on, hop-off opportunities on this charming St. Augustine trolley. The tour features over 20 stops near more than 100 attractions, so you have plenty of chances to hop on and hop off to see the sights up close.

On this St. Augustine tour you'll hear fun facts and intriguing insight about the Old Jail, Castillo de San Marcos Fort, and the other must-see points of interest that you’ll pass. The Old St. John's County Jail was home to all types of criminals during its 67-year stint as the county jail; the place is said to be a hub of paranormal activity as many visitors report hearing loud cries and seeing apparitions of former prisoners. Castillo de San Marcos Fort is the oldest masonry fort in the continental U.S. and has seen many a battle; the landmark was a constant site of warfare between opposing European powers from the 1500s to the 1800s. Hop back on the trolley and continue on to Flagler College, St. George Street, the Fountain of Youth, and the other points of interest on this tour.

The Old Jail Home to prisoners for over 60 years, the Old Jail in St. Augustine looks more like a resort than a maximum-security facility. The original structure was built in 1891 by Henry Flagler, and although it has been restored and renovated throughout the years, it looks very much the way it did when it opened over a century ago.

Today, visitors to the Old Jail can take a guided tour, learn about the many prisoners and practices that took place here and see where the Sheriff and his wife and family lived— adjacent to where the prisoners were housed. Meet Sheriff Joe Perry who had a reputation as being a harsh and strict warden – one of the toughest in the South. Walk through the men’s and women’s cells and see where executions took place in the gallows. Discover the history behind judicial practices in the 19th century and see an array of weapons and artifacts.

Adults and children are thoroughly entertained by our costumed actors who portray deputies from the early days and everyone gets a chance to try and escape! The Old Jail is one of just a few prisons of its kind still standing and makes for a great sightseeing and history adventure.

Colonial Quarter Tour Join us daily for our guided Historic Adventure tours and self-guided exploration—included in your admission ticket—as you journey through centuries of St. Augustine's rich history right in the heart of the downtown historic district. Your personal tour guide will share tales of St. Augustine's past as you're led through exciting activities like musket firing and cannon drills.

Experience this on your Historic Adventure Tour and much more! Take part in a musket drill with live firing demonstration and a cannon drill! Dig into archaeological evidence where one of St. Augustine's elusive first wooden forts likely stood! Experience the 16th Century boat project and blacksmithing through the ages! See historic preservation at work in the original 1740s de Mesa-Sanchez House! Learn about the melting pot of cultures that left their mark on St. Augustine from Native Americans and Minorcans to the Spanish, British and African-Americans! On your own, climb to the top of our interpretative 17th century watchtower for a stunning view of the Castillo de San Marcos and the Bayfront!

Please Note: There are 23 stops on this route and it takes approximately 80 minutes to complete the route without getting off. The trolleys run every 15 to 20 minutes. First and last tour times will be detailed in your electronic ticket.

The route includes the following stops:

• The Authentic Old Jail and Oldest Store Museum Experience
• Welcome Center on U.S. 1
• Visitors Information Center
• The Old Drugstore / Potter's Wax Museum / Tolomato Cemetery
• City Gate & St. George Street / Oldest Wooden Schoolhouse
• Colonial Quarter / Pirate & Treasure Museum
• Bay View at the Best Western
• Hypolita St.
• Flagler Memorial Presbyterian Church / Grace United Methodist Church / Ancient City Baptist Church
• Villa Zorayda
• Lightner Museum / Flagler College / Dow Museum of Historic Homes
• St. Augustine Distillery
• San Sebastian Winery
• Whetstone Chocolate Factory
• Plaza de la Constitucion / Government House / Cathedral Basilica of St. Augustine
• Spanish Military Hospital Museum / Ximenez-Fatio House
• Oldest House / Fernandez Llambias House
• Castillo de San Marcos
• Ripley's Believe It or Not!
• Welcome Center / Uptown San Marco Shopping District
• Mission of Nombre de Dios and Shrine of Our Lady of La Leche
• The Old Senator and Howard Johnson
• Fountain of Youth