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Discover St. Augustine’s history with the Trolley & Museums Combo, including the Old Jail, Oldest Store Museum, and the Historic Trolley for just $66 per person.
Explore the historic charm of St. Augustine with the Trolley & Museums Combo Package offered by Historic Tours of America. Priced at $66 per person and lasting one day, this tour opens the doors to the oldest city in the United States. It combines trolley transportation, guided tours, and entry to three key attractions: the Old Jail, the Oldest Store Museum, and the St. Augustine History Museum. This package is ideal for those eager to uncover over 400 years of history in a compact, easy-to-navigate format, making it perfect for families and history enthusiasts alike.
While the one-day duration offers a full experience, it’s important to note that the tour is designed for flexibility—you can hop on and off the trolley at more than 100 points of interest at your own pace. The guided tour of the Old Jail features engaging jailers, a close-up look at cells, maximum security areas, and a collection of weapons. The Old Store Museum offers a glimpse into turn-of-the-century inventions with lively demonstrations by friendly clerks, a snake oil salesman, and others dressed in period costumes. The History Museum provides an immersive journey through Florida’s evolution, with artifacts and unpublished photographs.
This tour is especially appealing for first-time visitors or those wanting a rundown of St. Augustine’s history without the hassle of individual ticket purchases. Plus, free parking at the Old Jail makes logistics straightforward. However, it’s worth mentioning that pets, large bags, and smoking are not permitted on the tour.


The tour begins at the booth by the Old Jail on 167 San Marco Ave. Travelers should plan to meet there for check-in, which makes the start straightforward. The entire experience is designed to be family-friendly and convenient, with free parking available. However, large bags and pets are not allowed, so packing light is recommended.
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The Old Jail serves as a central piece of this tour, with a guided experience led by jailers. Visitors get a close-up look at the men’s and women’s cells, as well as the maximum security area. The collections of weapons displayed add an authentic touch, making this stop especially engaging. The guides’ storytelling skills are praised as knowledgeable and friendly, adding depth to the experience.

The History Museum showcases a collection of authentic artifacts and unpublished photographs. It offers a rundown of the city’s history, emphasizing Spanish and British influences. Visitors learn about the evolution of St. Augustine and Florida, gaining a sense of how this city helped shape America’s past.

The Oldest Store Museum feels like traveling into a living Sears Roebuck catalog from 1908. Visitors witness demonstrations by friendly clerks, including a snake oil salesman and butcher, showcasing the latest inventions from 1900. The interactive displays give a vivid picture of turn-of-the-century life, making this a lively highlight of the tour.
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The trolley itself is more than just transportation; it’s a form of entertainment called transportainment. With more than 100 points of interest, travelers can hop on or off as they wish, exploring at their own pace. The live tour guides on the trolley are noted for their friendliness and knowledge, enhancing the overall experience.

Booking is easy and flexible—travelers can reserve now and pay later, with full refunds available if canceled up to 24 hours in advance. The tour is available in English and is designed to fit into a single day, with check availability for starting times.

The combo package offers a rundown of St. Augustine, combining transportation, guided insights, and multiple attractions into one cost-effective ticket. The experience guides are praised for their knowledge, humor, and hospitality, making learning about history enjoyable.

While the tour provides ample value, it’s limited to one day and excludes pets, large bags, and smoking. Visitors should wear comfortable shoes and plan to manage their own pacing within the attractions. The tour is suitable for those who enjoy historical storytelling and interactive exhibits in a family-friendly environment.

This $66 package offers great value for those interested in historic St. Augustine. The combination of trolley transport, guided jail tour, and museum visits ensures a well-rounded experience. It’s especially ideal for history buffs, families, and first-time visitors who want to maximize their time exploring the city’s 400+ years of history without the hassle of multiple ticket purchases.
While it might not suit those seeking a more in-depth or personalized tour, the friendly guides and easy access to key sites make this an attractive choice for a one-day adventure in Florida’s oldest city.
What is included in the tour?
The tour includes a ticket for the 1-day trolley, entry to the Old Jail, Oldest Store Museum, and the St. Augustine History Museum.
Where does the tour meet?
Guests meet at the booth by the Old Jail on 167 San Marco Ave for check-in.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.
Is there parking available?
Yes, there is free parking at the Old Jail location.
How long do the attractions take?
The entire experience is designed for one day, with flexibility to explore attractions at your own pace.
Are guides available during the tour?
Yes, the live tour guides are English-speaking and praised for their knowledge and friendliness.
Is this tour suitable for children?
Yes, the family-friendly nature and interactive exhibits make it a good choice for children.
Are pets allowed on the tour?
No, pets are not permitted on the tour.
What language is the tour conducted in?
The tour is conducted in English only.
How much does the tour cost?
The cost is $66 per person, offering good value for a full day of exploring St. Augustine.