St. Augustine, Florida, offers more than just historic charm—it’s a lively place to sample local brews, uncover ghost stories, and even explore its darker past. What makes it especially appealing for drinking tours is the city’s rich history, colorful legends, and lively pub scene, all within walking distance.
We’re particularly fond of the Beer & History Walking Tour because it combines a taste of craft beer with stories that date back to the city’s earliest days. Whether you’re a history buff or just want a fun way to explore, St. Augustine has something to offer.
If you’re considering which tour to pick, this guide will help you compare options—from a craft beer journey, to spooky pub crawls, to tales of pirates and true crime. Each offers a different way to enjoy the city’s vibrant bar scene while learning something new.
1. St. Augustine: Beer & History Walking Tour
For around $149 per person, the Beer & History Walking Tour offers an engaging 3-hour journey into both craft brewing and the city’s past. This tour stands out because it’s limited to small groups of 8 or fewer, ensuring a personalized experience.
You’ll visit historic streets and enjoy up to 12 beer tastings at local breweries—all paired with delicious food at the second stop, which adds a satisfying touch to the day.
What makes this tour particularly appealing is the blend of history and tasting. The guide shares stories behind St. Augustine’s oldest neighborhoods while you sample beers that reflect the city’s brewing revival. The inclusion of a food pairing is a bonus, providing a fuller experience than a typical tasting. The small group size means you’ll have plenty of time to ask questions and savor each sip.
Its high rating, 5/5 from three reviews, confirms it’s a top choice for those wanting a relaxed yet informative outing.
Bottom line: This tour is ideal if you want a deep dive into craft beer with historical context and personalized attention. It’s a bit pricier but offers a comprehensive taste of both the city’s past and present.
2. St. Augustine: True Crime Guided Pub Crawl
At just $35 per person for a two-hour adventure, the True Crime Guided Pub Crawl is a budget-friendly way to enjoy the city’s more sinister stories. This tour is especially suited for those intrigued by unsolved murders, serial killers, and dark legends from St. Augustine’s past.
The guide takes you to cozy pubs in the historic district, sharing tales of kidnapped priests, grisly murders, and infamous criminals that once haunted the city.
What makes this experience stand out is the storytelling. Guests come away with a vivid picture of the city’s darker side while enjoying a drink in a relaxed setting. The tour’s reviews, averaging 4.2/5 from 29 reviews, highlight its engaging narration and lively atmosphere.
It’s perfect for history lovers who prefer spooky stories over more traditional sightseeing. The casual pace allows for plenty of time to soak in the tales and chat with fellow participants.
Bottom line: This tour offers a fun, chilling look at St. Augustine’s real and often gruesome stories, all in a lively pub environment. It’s a great choice for those who want a quirky twist on the usual pub crawl.
3. St. Augustine: Haunted Pub Crawl
For $35 per person and lasting just two hours, the Haunted Pub Crawl delivers spooky stories and ghostly encounters on a walk through the Historic District. This tour is perfect if you’re drawn to ghost stories and the supernatural side of St. Augustine. You’ll visit some of the city’s most haunted bars, where the bartender might tell you about eerie encounters and spectral sightings.
The tour’s highlights include hearing some of the most gripping ghost stories in town and taking a ghostly stroll around the historic streets. The 4.1/5 rating from 37 reviews suggests it’s both fun and atmospheric. Guests often enjoy the mix of history, legend, and a bit of lighthearted spookiness. It’s suitable for a wide range of travelers, especially if you enjoy a good story and a drink.
Bottom line: If ghost stories and haunted pubs sound like your idea of fun, this tour will entertain with chilling tales and spirited drinks in spooky surroundings.
4. St. Augustine: Pirates and Privateers Pub Crawl
Priced at $35 per person for two hours, the Pirates and Privateers Pub Crawl explores St. Augustine’s pirate lore through lively storytelling and visits to historic pubs. The experience is centered around legendary tales of pirates targeting the city and how the Spanish defenses fought back. You’ll learn about the Castillo de San Marcos’ role as both fortress and prison for notorious rogues.
This tour is ideal for history and pirate enthusiasts who want a playful, storytelling approach to St. Augustine’s maritime history. The guide’s stories are filled with details about pirate attacks, pirate hideouts, and the city’s seafaring past. Although reviews are not available, the focus on pirate legends makes it a fun, thematic way to learn about the city’s adventurous side.
Bottom line: Perfect for those interested in pirate history, this pub crawl offers a spirited and educational experience with plenty of storytelling and lively tavern stops.
How to Choose the Right Drinking Tour
When deciding which tour fits your style, think about your interests and budget. If you love craft beer and history, the Beer & History Walking Tour offers a well-rounded experience, especially if you enjoy tasting and learning. For fans of spooky stories and ghostly legends, the Haunted Pub Crawl provides a fun, eerie journey.
Budget travelers on a tight schedule might prefer the True Crime Pub Crawl or the Pirates and Privateers crawl, both offering lively storytelling and historic insights at a lower price.
Consider your comfort level—if you’re interested in a more personalized experience, the small-group beer tour might be best. If spooky tales are more your speed, the haunted pub crawl will entertain. Also, think about timing: these tours work well in the cooler months when walking outdoors is more pleasant. Booking early is advised, especially for the popular beer tour.
Final Thoughts
St. Augustine’s drinking tours showcase the city’s diverse character—from craft beer and historic streets to ghostly legends and pirate stories. For those seeking a comprehensive taste of local brews along with history, the Beer & History Walking Tour stands out. If spooky stories resonate more, the Haunted Pub Crawl delivers a memorable, chilling experience.
Budget-conscious travelers will find the True Crime and Pirates crawls equally engaging, with the chance to learn and laugh.
No matter your preference, booking early and choosing a tour aligned with your interests will maximize your enjoyment of this charming city. With so many options, St. Augustine promises memorable stories and plenty of good drinks—so raise your glass and start planning your visit.