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St. Augustine Day Trip | April 28, 2026

1 days
St. Augustine
Starting from $175

Travel from your Jacksonville hotel to St. Augustine and spend the day exploring this beautiful city, rich with more than 500 years of history.

Upon arrival, you will visit the Old Jail for a guided tour of this 1891 landmark, now transformed into a living museum. As you walk through the cells and exhibits, you will gain insight into what life was like for those once incarcerated there.

After your visit, enjoy a hop-on, hop-off trolley tour featuring 22 stops and fully narrated commentary throughout the city. The complete route covers 8.5 miles and takes approximately 90 minutes from start to finish. Trolleys arrive at each stop approximately every 15 minutes between 9:00 AM and 4:30 PM, allowing you to explore at your own pace.

We recommend stopping at Castillo de San Marcos, the 17th-century Spanish fort that stands as the oldest masonry fort in the continental United States. Your ticket also includes complimentary admission to the St. Augustine History Museum. The trolley route travels through the Historic District, St. George Street, Lincolnville, and Plaza de la Constitución, and also offers a complimentary shuttle to St. Augustine Beach.
After a full day of exploration, you will return to Jacksonville by motorcoach.

What’s Included

  • Old Jail Tour
  • Trolly Tour
  • Transportation to and from St. Augustine
  • EO Staff Assistance

Daily Itinerary

Day 1 Trolley Stops

1.    Old Jail
2.    Visitor Information Center
3.    Potter's Wax Museum
4.    City Gates
5.    Colonial Quarter
6.    Best Western/Bay Views
7.    St. George Street: Pedestrian-only epicenter of downtown St. Augustine.
8.    Churches
9.    Villa Zorayda Museum
10.    Lightner Museum
11.    Lincolnville Museum & Cultural Center
12.    St. Augustine Distillery (not open)
13.    San Sebastian Winery
14.    Plaza de la Constitución
15.    St. Augustine Municipal Marina
16.    Oldest House
17.    Castillo de San Marcos
18.    Ripley's Believe It Or Not
19.    Old Town Trolley Welcome Center
20.    Mission Nombre de Dios
21.    Old Senator Tree & Villa 1565
22.    Fountain of Youth

Departure Dates

  1. Tuesday, April 28, 2026
    From $175* Register Now!