There is a reason St. Augustine is called the “Ancient City.” Founded in 1565, it is a place where cobblestone streets tell stories of Spanish explorers, pirate raids, and Gilded Age glamour. But if you’ve ever tried to drive there yourself, you know that the modern-day struggle of traffic and parking can quickly dampen the historical magic.
That’s where Terry’s Rides comes in. We believe your vacation should start the moment you leave your driveway. Our Curated St. Augustine Day Trip is designed to give you a VIP experience in America’s oldest city, all from the comfort of our luxury 2025 Hyundai Palisade.
Here is what your perfect day with Terry looks like:
Morning: The Arrival in Style
Forget GPS stress and highway fatigue. Relax in our climate-controlled cabin with a cold water in hand while Terry handles the drive. We’ll drop you off right at the heart of the historic district, steps away from the iconic Castillo de San Marcos.
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Terry’s Tip: Start your day early at the fort to watch the morning sun hit the Matanzas Bay. It’s the oldest masonry fort in the continental U.S. and a must-see for the incredible views from the gun deck.
Mid-Day: Cobblestones and Culture
After exploring the fort, take a short stroll to St. George Street. This pedestrian-only thoroughfare is the pulse of the city, lined with boutique shops, live music, and the “Oldest Wooden Schoolhouse.”
For lunch, the options are endless, but Terry’s favorites include:
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Columbia Restaurant: For world-famous Spanish-Cuban cuisine in a stunning courtyard.
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Obi’s Fillin’ Station: For a more casual, retro vibe with some of the best burgers in town.
Afternoon: Flagler’s Legacy
No trip to St. Augustine is complete without witnessing the architectural marvels of Henry Flagler. We can swing by Flagler College (formerly the Ponce de Leon Hotel) to admire the Tiffany stained glass, or the Lightner Museum, housed in the former Alcazar Hotel.
If you’re looking for something more spiritual and serene, we’ll head to the National Shrine of Our Lady of La Leche at Mission Nombre de Dios, the site of the first parish mission in the United States.
Late Afternoon: The Scenic Route Home
As the day winds down, Terry will be waiting exactly where you left him. No searching for your car in a crowded parking garage or navigating out of the city in rush hour. On the ride home, feel free to scroll through your photos or even take a nap in the Palisade’s plush seating.
Why Book St. Augustine with Terry’s Rides?
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Door-to-Door Service: We pick you up and drop you off at your home or hotel.
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Luxury & Safety: Travel in a brand-new 2025 vehicle with a fully licensed and insured professional driver.
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Custom Itineraries: Want to spend more time at the St. Augustine Lighthouse and less at the shops? We work around your schedule.
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Stress-Free Parking: We handle the logistics so you can focus on the history.
Ready to Explore?
Florida’s history is waiting, and Terry is ready to take you there. Space for our curated day trips fills up fast, especially during the beautiful Florida winter and spring seasons!
Book your St. Augustine Adventure today: 📞 Call/Text Terry: (352) 364-7432
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- The oldest continuously inhabited European-established settlement in North America
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- Located on Anastasia Island, just steps from St. Augustine Beach, Obi’s Fillin’ Station is your one-stop-shop for burgers.
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- Strategic cannon placement and star-shaped design. There is a reenactment of Spanish soldiers with firing cannons. demonstration.
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- Monument at The Cathedral Basilica of Saint Augustine in memory of Father Pedro Camps, who led the Minorcan Colony to St. Augustine, Florida.