: Step back in time with pastime private historical tours

Experience the Charm of St. Augustine with a Private 1920s-Style Tour

Imagine cruising through one of America’s oldest cities in a vintage automobile, with a guide dressed in period attire, sharing stories that bring St. Augustine’s history to life. For just $37.50 per person, you get roughly an hour and a half of personalized exploration, complete with round-trip transportation from your downtown hotel. This private tour, led by friendly and knowledgeable guides, focuses on small groups (up to four people), ensuring a cozy, engaging experience that’s perfect for history buffs, romantic couples, or families seeking an authentic peek into the city’s past.

What we love most about this tour is the personalized storytelling that makes history feel alive, plus the vintage vehicle ride which adds a touch of nostalgia and fun. The guides are praised for their passion and sense of humor, making even the most historical sites enjoyable. One small consideration is that the vintage automobile, though charming, might be tight for larger or taller guests, as some reviews suggest a preference for only three people in the back seat for comfort. Still, the personalized nature of the experience makes it a standout choice for those wanting an intimate, memorable glimpse of St. Augustine.

This tour best suits travelers who value personal interaction, off-the-beaten-path stories, and a unique transportation experience. It’s especially ideal if you’re staying downtown, love history, or want a fun, relaxed way to see key sites without the hustle of larger tour groups.

Key Points

• Private and Personalized: Only your group participates, with a driver-guide who offers tailored attention.
• Vintage Ride: The tour takes place in a charming 1920s-themed vehicle, adding a historical flavor.
• Expert Guides: Guides are praised for their knowledge, humor, and personal touches.
• Flexible & Convenient: Includes hotel pickup and drop-off, making it easy to fit into your schedule.
• Short but Impactful: With about 90 minutes, it’s a perfect introductory overview or a romantic outing.
• Family & Small Group Friendly: Best for up to four people, ensuring a comfortable and intimate experience.

A Deep Dive into the St. Augustine Private Tour

The Experience and Its Setting

This private tour is set in St. Augustine, Florida, the oldest city in the United States, packed with stories that span from early Spanish settlers to the Gilded Age. The meeting point is conveniently located at 11a Aviles St, the heart of historic St. Augustine, making it accessible whether you’re arriving by hotel, cruise, or public transport.

What makes this tour stand apart is the 1920s theme—both the vehicle and the guide’s attire evoke the era, giving you a sense of stepping back in time. The vintage automobile isn’t just a mode of transport but part of the story itself, making the ride feel like a scene from a bygone era. The small group size ensures you get plenty of attention, and guides like Don are frequently praised for their enthusiasm, humor, and depth of knowledge.

What You Will See

The tour covers the most significant sites of historic St. Augustine, including Castillo de San Marcos, Flagler College, the Old City Gates, and the lively St. George Street. The guide’s storytelling weaves the facts with haunted tales and fascinating anecdotes, transforming a simple city tour into a lively history lesson.

Several reviewers mention how Don or other guides take time to answer questions, making it very interactive. One reviewer notes that Don’s sense of humor makes the experience even more memorable, turning historical facts into engaging stories.

The Itinerary in Detail

• Start at Aviles Street: This historic street is the oldest in the U.S., lined with charming shops and restaurants. Your guide will begin here with a brief overview of the city’s founding and early Spanish influence.

• Castillo de San Marcos: The oldest masonry fort in the continental U.S., this site is a highlight for its impressive construction and strategic significance. The guide will share stories about its role in various conflicts and the pirates who once prowled nearby.

• Flagler College: An architectural gem, originally built as a luxury hotel by Henry Flagler, a railroad magnate. The guide will detail its transformation into a college and its significance in the Gilded Age.

• Old City Gates and Walls: Once the main entrance to the city, these gates are a tangible reminder of the city’s colonial past. The stories about defense and trading routes add depth to the visual experience.

• St. George Street: The bustling pedestrian street offers a mix of shops, eateries, and historic buildings. The guide might share local legends and lesser-known facts about this lively corridor.

Authentic Stories and Local Legends

Many reviews highlight how the guide’s storytelling elevates the experience. For example, one reviewer mentions that their guide “not only showed the sites but shared the stories that go with them,” making history compelling and fun. Others appreciated the haunted tales, which add an extra layer of intrigue to the city’s dark corners.

The Transportation Experience

Riding in a vintage, 1920s-style vehicle is more than just a mode of transport; it’s a nostalgic journey. The open-air feel of the vehicle offers unobstructed views, perfect for snapping photos or simply soaking in the sights. The driver’s friendly demeanor and the period attire of the guide create a fun, immersive atmosphere.

A common theme in reviews is how Don’s kindness and humor make the ride enjoyable for all ages. One reviewer specifically mentions how their 95-year-old father enjoyed the ride, highlighting its accessible and family-friendly nature.

Duration and Booking

The 1 hour and 30-minute length is ideal for a quick yet rundown. The tour is booked on average 24 days in advance, which indicates it’s popular among visitors seeking a personalized, memorable experience. The price of $37.50 per person is a good value considering the personalized service, the vintage ride, and the stories shared.

Round-trip hotel pickup adds convenience, especially if you’re already exploring downtown or staying nearby. The tour’s private nature means no crowded buses or trolley schedules—just your small group and a passionate guide.

The Reviews: Authentic Voices

With a 5.0 rating from 242 reviews, this tour clearly hits the mark. Many travelers praise guides like Don for their knowledge, entertainment skills, and personal touches. From romantic anniversaries to educational outings for families, the tour resonates across different types of visitors.

One review mentions how the small group size makes it easier to ask questions and engage deeply with the sites. Another highlights how the fun in the vintage vehicle adds a playful element to the historical exploration.

Considerations and Tips

While most feedback is positive, a few reviews note that the back seat in the vintage car might be tight for larger guests, especially with four people. If you’re tall or prefer more space, it might be worth requesting a smaller group or sitting in the front.

Also, the tour focuses on historic sites and storytelling—it doesn’t involve walking or extensive physical activity—making it suitable for most travelers with moderate mobility.

Who Should Book This Tour?

This experience is perfect for history enthusiasts who want a personal, storytelling-led overview of St. Augustine’s most famous sites. It’s also ideal for romantic couples seeking a charming, intimate outing, or families with kids (or grandparents) who enjoy engaging stories and a fun vintage ride.

If you prefer a small-group, personalized experience over large bus tours, this private tour offers a relaxed and friendly atmosphere. It’s especially appealing if you enjoy quirky, themed transportation and want to learn about the city beyond just the guidebook facts.

FAQs

Is this tour suitable for all ages?
Yes, most travelers can participate, and the stories and vintage vehicle are enjoyable for a wide age range. Just be mindful of space constraints in the vehicle for larger guests.

How long is the tour?
About 1 hour and 30 minutes, making it a good overview without feeling rushed.

Does the tour include hotel pickup?
Yes, round-trip transportation from your downtown hotel is offered, which is very convenient.

Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the experience, giving you flexibility.

What is the price per person?
$37.50, which is quite reasonable for a private, personalized experience in a vintage vehicle.

Are there any special requirements?
Most travelers can participate. Service animals are allowed. For comfort, consider the seating arrangement if you’re larger.

What sites will we see?
The tour covers key historic sites like Castillo de San Marcos, Flagler College, the Old City Gates, and St. George Street, with stories to match.

Is this a group tour or private?
It’s a private tour for your group only, ensuring a personalized experience.

What makes this tour stand out?
The combination of personalized storytelling, vintage transportation, and small group intimacy makes it a unique way to experience St. Augustine.

Final Thoughts

For travelers seeking a blend of history, fun, and intimacy, this private, vintage-style tour offers a wonderful way to explore St. Augustine. The guides’ knowledge and humor turn the city’s stories into lively narratives, while the classic vehicle adds a playful, nostalgic touch.

If you’re looking for a relaxed, authentic experience that avoids the crowds and offers personal attention, this tour hits the right notes. It’s especially well-suited for those who appreciate small-group adventures, love history, or want a charming, memorable ride through one of America’s most picturesque old towns.

This tour delivers value and character, making it a highlight for anyone eager to get a genuine feel for St. Augustine’s past and present.