St. Augustine, Florida, isn’t just the nation’s oldest city; it’s also a fantastic place to explore with a drink in hand. With its charming streets, historic taverns, and lively bar scene, it’s a natural fit for drinking tours that combine local history and fun stories. Our favorites include a craft beer and history walk that offers a taste of authentic brews alongside fascinating tales, and the haunted pub crawl where you can toast ghost stories in some of the city’s oldest bars. Whether you’re after a laid-back beer tasting or an eerie night exploring haunted pubs, St. Augustine has something to offer.
One tour that stands out is the Beer & History Walking Tour. It’s perfect if you want to combine local craft breweries with a deep dive into the city’s past. Meanwhile, the True Crime Guided Pub Crawl appeals to those interested in the darker side of St. Augustine’s history, and the Pirates and Privateers Pub Crawl is a hit for fans of salty stories and high-seas mischief. Each tour showcases a different side of this charming city, making it easy to find one that fits your interests and budget.
1. St. Augustine: Beer & History Walking Tour
At number 1, the Beer & History Walking Tour is a standout for those who want a relaxed yet engaging way to sample local brews. For $149 per person and lasting about 3 hours, this tour offers a fantastic balance of craft beer tasting and historic strolls through St. Augustine’s streets. Small groups—limited to 8 guests—ensure a personalized experience as your guide shares insights into the city’s past while you sample up to 12 beers.
What makes this tour unique is its combination of beer tastings with a narrative about the city’s history, culminating in a delicious food pairing at the second stop. The guide’s knowledge makes the stories of the city come alive, from Spanish colonial days to modern craft brewing. Guests rave about the quality of the breweries visited and the intimate atmosphere. If you’re a beer lover who also enjoys learning about local history, this tour balances both perfectly.
Bottom Line: This tour is ideal for those who want a comprehensive experience that combines tastings, storytelling, and a walk through St. Augustine’s historic streets. It’s a bit pricier but offers a well-rounded, memorable day.
2. St. Augustine: True Crime Guided Pub Crawl
At number 2, the True Crime Guided Pub Crawl offers a different kind of history—one filled with murder, mystery, and unsolved crimes. For just $35 per person and lasting around 2 hours, this tour takes you through St. Augustine’s art district and local pubs while revealing stories of serial killers, kidnapped priests, and grisly murders. Your guide’s storytelling brings these dark tales to life in a cozy pub setting.
What sets this tour apart is its focus on true crime stories that have left their mark on the city. Guests can sip on a locally brewed beer or other beverage as they listen to tales of bloodshed and secrets from centuries past. The combination of walking and pub stops makes for an engaging half-day, especially for those interested in the city’s shadowy side.
Guests describe it as a gripping and fun way to explore St. Augustine’s past, with stories that linger long after the tour ends. It’s perfect for travelers who love a little suspense with their drinks.
Bottom Line: Ideal for fans of crime stories and dark history, this tour offers a lively mix of storytelling and bar hopping. It’s affordable and packed with intrigue.
3. St. Augustine: Haunted Pub Crawl
Number 3 on our list is the Haunted Pub Crawl, which is perfect if you want a spooky twist on your night out. For $35, this 2-hour tour takes you through some of the city’s most haunted bars in the Historic District. Along the way, you’ll hear ghost stories that have been passed down through generations and uncover the city’s haunted secrets.
What makes this tour stand out is the combination of history and ghost stories in an atmospheric environment. Your guide shares tales of spectral sightings, mysterious disappearances, and the spirits believed to linger in these historic pubs. During the walk, you’ll also toast to the spirits—both supernatural and the living.
Guests often mention how engaging the stories are, and the eerie atmosphere that makes the experience memorable. The tour is especially suited to those who enjoy ghost stories and want to explore the city’s haunted reputation. It’s a fun way to combine history, spirits, and a little adrenaline.
Bottom Line: This tour is perfect for ghost lovers and those wanting a fun, spooky night with a drink in a historic setting. It’s a spirited experience that’s both entertaining and chilling.
4. St. Augustine: Pirates and Privateers Pub Crawl
Finally, the Pirates and Privateers Pub Crawl offers a salty adventure for anyone interested in pirates, privateers, and the high seas lore of St. Augustine. Priced at $35 for around 2 hours, this tour takes you through lively pubs with stories of salty pirates, why they targeted the city, and how Spanish defenders fought back.
What makes this experience special is its focus on pirate history with stories about famous pirates and the strategic importance of the Castillo de San Marcos. You’ll visit multiple pubs, with time to enjoy a drink and listen to tales of sea battles, treasure hunts, and pirate legends. It’s a lively, fun tour that combines history, humor, and a bit of mischief.
Guests appreciate the storytelling about why pirates targeted St. Augustine and the role of the fortress in defending the city. It’s most suited for those interested in maritime history and pirate lore, offering a playful but informative night out.
Bottom Line: This tour fits well for anyone looking to combine history with a lively pub environment and enjoy stories of pirates and privateers.
$35 per person
How to Choose Your Perfect Drinking Tour
Picking the right tour depends on your interests and how much time and money you want to invest. If you’re enthusiastic about craft beer and history, the Beer & History Walking Tour offers a full, immersive experience, perfect for a leisurely day. For a more thrilling, spooky night, the Haunted Pub Crawl provides ghost stories in historic bars, ideal for those who love a good scare.
Travelers interested in the darker side of St. Augustine’s past should consider the True Crime Pub Crawl—a budget-friendly way to enjoy storytelling with a sinister twist. Meanwhile, fans of pirates and seafaring tales will enjoy the Pirates and Privateers Pub Crawl, especially if they want to learn about the city’s role in high-seas adventures.
When planning, consider booking early, especially for tours that are popular or limited in size. Also, check if any tours fit your schedule—most are around 2-3 hours, making them easy to fit into a day or evening.
Final Thoughts
St. Augustine offers a diverse array of drinking tours that reveal its historic, haunted, and pirate-filled past. Whether you want to sip craft beers while learning about the city’s colonial days, hop between haunted pubs, or explore the legend of pirates, there’s a tour for you.
For a well-rounded experience, the Beer & History Walking Tour is hard to beat, offering a perfect mix of tastings and storytelling for a memorable day. If you’re interested in dark tales or ghosts, the Haunted Pub Crawl makes for a fun, spooky night. And for those fascinated by pirates, the Pirates and Privateers Pub Crawl will satisfy your high-seas curiosity.
Booking early is recommended to secure your spot on these popular experiences. Whatever your choice, exploring St. Augustine’s drinking scene promises an authentic glimpse into its colorful past—one sip at a time.