St Augustine History and Cheesecake Golf Cart Tour

Imagine cruising through the cobbled streets of one of America’s oldest cities in a private golf cart, feeling the warm breeze, and soaking up the sights with minimal fuss. That’s exactly what the St Augustine History and Cheesecake Golf Cart Tour promises—a relaxed, personalized way to explore the city’s most iconic landmarks. This tour is perfect for those who want a deeper, more intimate experience than a typical trolley or bus ride, combined with a sweet finish that’s hard to beat.

Two things we love about this tour are the small group size and knowledgeable guide—both making the experience feel personal and engaging—and the delicious cheesecake and wine pairing at the end, which adds a memorable culinary twist. One thing to keep in mind is that the tour is not suited for children or travelers with serious medical conditions, and there’s a minimum of four participants required. But if you’re seeking a flexible, authentic way to see St Augustine’s highlights with a touch of indulgence, this could be your ticket.

Key Points

• Private, intimate experience perfect for small groups or couples.
• Expert-guided tour with detailed insights into the city’s landmarks.
• Comfortable golf cart transportation allowing easy access to narrow streets.
• Includes treats and tastings, making it a multi-sensory experience.
• Flexible itinerary with multiple iconic stops, from fortresses to historic streets.
• Great for travelers looking for a relaxed and personalized sightseeing day.

A Closer Look at the Itinerary

This tour carefully balances sightseeing, storytelling, and tasting, with a well-thought-out itinerary that hits many of St Augustine’s highlights. Starting at Plaza de la Constitución, the tour sets the tone with a brief introduction, giving context to the city’s heritage before jumping into the sights. The small group arrangement means you won’t be just another face in a crowd—your guide can tailor insights and answer questions as you go.

Next, cruising down St. George Street, you’ll see the well-preserved Spanish colonial architecture that defines the city’s historic center. This bustling pedestrian street is a visual feast, lively with shops, cafes, and history. The guide’s commentary enriches the experience, pointing out details you might overlook on your own.

From there, the tour moves along the hotel district to admire Flagler College, originally a luxurious hotel from the Gilded Age, now a splendid academic institution. You’ll also pass the Villa Zorayda Museum, an ornate Moorish-style home that echoes the city’s eclectic architectural history. Both stops are driven-by observations with commentary—no long walks—but they pack plenty of visual and historical interest.

The Lightner Museum, housed in the former Alcazar Hotel, offers a glimpse into the grandeur of the Flagler era. While you won’t go inside, the exterior and stories about the building’s past as a social hub for the wealthy add context to your journey. Similarly, passing the Lincolnville Museum and Cultural Center, you get a sense of the city’s civil rights history, adding depth to your understanding of St Augustine’s diverse heritage.

The tour also takes you past the San Sebastian Winery, a local favorite, and the Castillo de San Marcos National Monument—the oldest masonry fort in the US, built in 1695. From up close, the fort’s sturdy stone walls and commanding position make it a highlight, perfect for history buffs.

Other notable sights include the Mission Nombre de Dios, site of early Thanksgiving celebrations, and the legendary Fountain of Youth Archaeological Park—famous for the Ponce de Leon legends and the beautiful Magnolia Street, ranked among the US’s most scenic streets.

The Sweet Ending: Cheesecake and Wine

The highlight for many visitors is the visit to Bar Harbor Cheesecake Company, where the tour culminates with sampling three different cheesecake flavors paired with wine. This isn’t just a sweet treat—it’s a carefully curated tasting experience designed to enhance the flavors and complement the wines. As one reviewer noted, “the cheesecake was delicious, and the wine pairing made it even better,” adding an indulgent finish to an already rich day of sightseeing.

This stop is included in the tour fee, making it excellent value for a unique culinary experience. It’s a relaxed, friendly way to conclude, giving you the chance to chat with your guide and fellow travelers while savoring some of the best local desserts.

Transportation and Group Size

Traveling in a private golf cart means you’ll gain access to narrow, historic streets that larger tour buses can’t reach. The ride is comfortable, and the small group—up to nine travelers—ensures plenty of space for personal interaction and questions. The tour lasts about 1 hour and 30 minutes, which is a good length for absorbing the sights without feeling rushed.

Starting at 4:00 pm from 38 Cathedral Place, the timing offers a relaxed late-afternoon experience, perfect for winding down your day or combining with other activities. The tour’s limited capacity means a more intimate experience, and the guide’s local knowledge is a big plus.

What the Reviews Say

Guests consistently praise the knowledgeable guides and the quality of the storytelling. Sandra shared, “The driver was very knowledgeable and pleasant, and we enjoyed the snacks along the way,” emphasizing the friendly atmosphere. Christine appreciated the private, small-group approach, saying, “We were able to see things the larger trolley tours cannot, and it was perfect during Covid times.”

The inclusive treats and wine samples are another highlight, with many noting that the cheesecake and wine pairing added a special touch to the day. The relaxed pace, combined with authentic insights into St Augustine’s history and architecture, makes it clear why this tour earns a high rating.

The Value Proposition

At $69 per person, this tour offers a blend of sightseeing, education, and indulgence that is quite attractive. Compared to larger, less personalized options, you get the benefit of a private, guided experience that maximizes comfort and insight, especially in a city dense with history and picturesque streets.

The inclusion of desserts and wine adds to the perceived value, transforming a typical sightseeing tour into a memorable occasion. Plus, the small group size means you have ample opportunity to ask questions and customize your experience to some extent, all while avoiding the crowds.

Who Will Love This Tour?

This experience is ideal for travelers who seek a more intimate, relaxed exploration of St Augustine—perfect for couples, small groups, or solo travelers looking for a personal touch. It’s especially suitable if you’re eager to learn about the city’s history but prefer a comfortable, less hurried format.

It’s also great for those who appreciate culinary treats as part of their sightseeing, making the cheesecake and wine stop a memorable highlight. Be aware that it’s not recommended for children or travelers with serious medical issues, and a minimum of four participants is needed to run the tour.

Frequently Asked Questions

Is this tour suitable for kids?
This tour is not recommended for children, mainly because of the adult-focused tasting and the medical considerations for some travelers.

How long does the tour last?
The tour is approximately 1 hour and 30 minutes long, making it a manageable length to enjoy without feeling exhausted.

What is included in the price?
The fee covers a private guide and golf cart, three cheesecake flavors, and three wine samples, offering a well-rounded experience.

Where does the tour start and end?
It begins at 38 Cathedral Place and concludes back at the same meeting point, making logistics simple.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, making it flexible for last-minute adjustments.

Is this a group tour?
It’s a small, private tour with a maximum of 9 travelers, ensuring a personal experience.

For anyone wanting a personalized, insightful way to explore St Augustine, this golf cart tour hits the mark. It combines the best of sightseeing, local storytelling, and culinary delight—all in a relaxed, manageable package. The small group size and knowledgeable guide help bring the city’s history and culture to life, while the cheesecake and wine tasting add a memorable finishing touch.

If you value comfort, authenticity, and a touch of indulgence, this tour offers great value and a chance to truly enjoy the Ancient City. It’s especially suited for couples, small groups, or solo travelers who want a more intimate experience than the big bus tours.

In short, this tour balances historical insights with fun, flavorful stops—making it a worthwhile addition to any St Augustine visit. Just remember to book ahead, as the small group size and popularity mean it fills up quickly.