Dark History Pub Crawl from Saint Augustine

Explore St. Augustine's dark side with this engaging pub crawl. Discover haunted hotspots, spooky stories, and historic pubs—all led by expert guides.

Planning a trip to St. Augustine and craving something beyond the usual sightseeing? If you’re intrigued by ghost stories, eerie legends, and the city’s haunted past, the Dark History Pub Crawl from Kindred Spirits Tours might just be your cup of tea. Although we haven’t taken this tour ourselves, the glowing reviews and detailed itinerary suggest it’s a well-crafted experience, perfect for those curious about the spooky stories lurking in America’s oldest city.

What we love about this tour is how it combines authentic dark history rooted in research with lively storytelling. Plus, stopping at historic pubs adds a fun, social aspect to the experience. But, a word of caution: it’s primarily an evening activity, so if you’re not into late-night ghost tales, it might not be your best pick. This tour seems ideal for history buffs, ghost enthusiasts, or anyone looking for a different way to explore St. Augustine’s storied streets.

One potential downside? The tour is relatively short—about 2 to 3 hours—and while the stories are immersive, the focus on dark history and drinks might not be for everyone. Still, if you’re after a mix of spooky tales and local pub atmosphere, this could fit perfectly into your itinerary.

And most importantly, if you’re looking for a guided experience led by knowledgeable storytellers who take their research seriously, this tour seems to deliver. It’s especially suited for travelers eager to combine history and ghost stories with a social, laid-back vibe.

Key Points

Dark History Pub Crawl from Saint Augustine - Key Points

  • Deeply researched stories rooted in authentic haunted history of St. Augustine.
  • Engaging storytelling led by passionate guides who love sharing tales.
  • Visits to historic pubs where spirits are said to linger, offering a mix of history and fun.
  • Includes free mimosas at the start, adding a light, celebratory touch.
  • Group size limited to 12, keeping things intimate and manageable.
  • Flexible booking with free cancellation, making it low-stress to try out.

What to Expect from the Dark History Pub Crawl

Dark History Pub Crawl from Saint Augustine - What to Expect from the Dark History Pub Crawl

The tour kicks off at the charming Golden Gypsy, where you’ll start with a friendly meet and greet over complimentary mimosas. It’s a great way to settle in and get introduced to the group. The host’s enthusiasm and knowledge shine through from the start, setting a lively, intriguing tone.

From there, you’ll stroll through St. Augustine’s historic district, visiting four popular bars and pubs. Each stop is associated with stories of hauntings and tragedies specific to the city—places where the spirits are believed to linger over centuries. We loved the way the guide seamlessly weaves history with supernatural tales, making each location come alive with atmosphere.

While the itinerary might vary based on availability, the overall flow—starting with a cozy introduction and moving through haunted hotspots—remains consistent. Expect to learn not just spooky legends but also the historical context behind them. This makes for a more meaningful experience, especially for those who enjoy stories rooted in real events.

The First Stop: The Golden Gypsy

Dark History Pub Crawl from Saint Augustine - The First Stop: The Golden Gypsy

We loved that the tour begins in such a welcoming spot. The Golden Gypsy offers a relaxed environment where you can browse unique gifts and artwork upstairs, setting a creative, slightly mystical mood. The free admission and the chance to buy jewelry for protection add a little extra fun. It’s a perfect warm-up before heading into the dark tales ahead.

Walking Through Haunted Downtown St. Augustine

After a quick story and a sip, you’ll set out on foot to explore four of the city’s most iconic bars and historic sites. The guide’s storytelling turns each location into a portal to the past—tales of tragic love, murders, and unexplained phenomena that have left their mark on these walls.

The group size stays small—capped at 12—which makes for a personal, engaging experience. You’ll get to ask questions, take photos, and soak in the atmosphere without feeling rushed.

A couple of reviews highlight how knowledgeable and lively the guides are. One noted, “Our guide has so much knowledge of the history of St. Augustine and has a fun personality!” This makes the experience not just educational but also genuinely entertaining.

What’s Included and What’s Not

Dark History Pub Crawl from Saint Augustine - What’s Included and What’s Not

The free mimosas at the start are a nice touch, helping you loosen up and get into the spirit of things. However, remember that alcoholic drinks at the pubs are not included, so your tab will depend on what you order at each stop. The tour doesn’t include meals, so if you’re hungry, plan to grab some snacks beforehand or afterward.

The guide is English-speaking, making it accessible for most travelers. Plus, the tour is designed to be inclusive—service animals are allowed, and most travelers should be able to participate comfortably.

The Experience Duration and Group

Dark History Pub Crawl from Saint Augustine - The Experience Duration and Group

Clocking in at about 2 to 3 hours, this tour is a manageable evening activity. It’s ample time to enjoy the stories, drinks, and atmosphere without it feeling like a marathon. The small group size creates an intimate setting where everyone can connect and feel involved.

How the Tour Feels in Practice

Dark History Pub Crawl from Saint Augustine - How the Tour Feels in Practice

From what the reviews suggest, attendees generally have a fantastic time. They rave about the guide’s storytelling skills and deep research, which makes the stories feel both authentic and captivating. One reviewer mentioned, “Don’t miss out, book now!” because the storytelling is truly unique.

The experience seems well-paced, with enough time at each stop to enjoy a drink, absorb the tales, and get a sense of the city’s haunted charm. The combination of historic pubs and haunted legends makes for a memorable evening.

Is It Worth the $40 Price Tag?

Dark History Pub Crawl from Saint Augustine - Is It Worth the $40 Price Tag?

Considering that the tour includes a guided experience, free drinks at the start, and stops at several historic spots, $40 per person feels reasonable. You’re paying for quality storytelling and a fun social outing in a city renowned for its ghostly lore. If you’re into history, ghost stories, or just looking for a unique way to see St. Augustine, this tour offers good bang for your buck.

Who Should Book This Tour?

Dark History Pub Crawl from Saint Augustine - Who Should Book This Tour?

This experience is perfect if you’re okay with walking around historic areas, enjoy stories about ghosts and tragedies, and want an engaging guide to bring the past to life. It’s especially suited for those who appreciate well-researched tales and lively storytelling rather than scripted or overly theatrical presentations.

While not explicitly kid-friendly, it’s probably best suited for older children or teenagers who can handle spooky stories in a social setting. The small group size and casual vibe also make it ideal for couples, friends, or solo travelers looking to meet others.

Final Thoughts

The Dark History Pub Crawl from Kindred Spirits Tours offers a compelling mix of history, ghost stories, and local pub culture. It’s a fantastic way to learn about St. Augustine’s haunted past in a relaxed, social setting. The guides’ knowledge and storytelling flair truly elevate the experience, making each stop memorable.

If you’re after an evening filled with chilling tales, atmospheric pubs, and a touch of the supernatural, this tour deserves a spot on your itinerary. It’s a vivid, entertaining, and insightful way to explore one of America’s most ghostly cities.

✨ Book This Experience

Dark History Pub Crawl from Saint Augustine



5.0

100% 5-star

“We had the best time! Our guide has so much knowledge of the history of St. Augustine and has a fun personality! We highly recommend this tour.”

— A Tripadvisor Reviewer, Jul 2025

Frequently Asked Questions

Is this tour suitable for families or children?
While the tour is generally casual and fun, it focuses on ghost stories and dark history, so it’s probably better suited for older teens or adults. It’s not explicitly marketed as family-friendly.

How long does the tour last?
Expect about 2 to 3 hours, making it a perfect evening activity without feeling rushed.

Are drinks included in the price?
No, the tour offers free mimosas at the start, but drinks at the pubs are at your expense.

What’s the meeting point?
The tour begins at 23 Cuna St, St. Augustine, FL 32084, and ends back at the same spot.

Can I cancel the tour if my plans change?
Yes, you can cancel for a full refund up to 24 hours in advance. Cancellations within 24 hours are not refundable.

Is the tour accessible for most travelers?
Yes, most travelers can participate, and service animals are allowed.

Is the group small or large?
The group size is limited to 12, ensuring a more personal experience.

What’s the main draw of this tour?
It’s the authentic, well-researched ghost stories combined with visits to historic pubs, all led by engaging guides.

How does the storytelling enhance the experience?
The guides’ passion and research transform the city’s haunted past into captivating, memorable stories that stick with you long after.

Whether you’re a ghost enthusiast, history lover, or just looking for a fun night out, the Dark History Pub Crawl in St. Augustine offers a unique glimpse into the city’s spooky side. It’s a lively, authentic experience that balances storytelling, history, and a bit of good old-fashioned ghostly fun.