St. Augustine: Pirates and Privateers Pub Crawl

If you’re craving a different way to experience the oldest city in the U.S., the Pirates and Privateers Pub Crawl by Ghost City Tours offers a spirited hour or two filled with salty stories, historic lore, and a taste of the city’s pirate roots. This tour promises a lively mix of storytelling, local taverns, and the chance to show off your best pirate lingo—what’s not to love?

We’re fans of how this tour combines entertainment with education, providing engaging guides and authentic tales that bring St. Augustine’s lawless past to life. The opportunity to enjoy a few drinks in historic venues makes it a memorable, fun-filled outing. One possible hiccup? The two-hour length means you’ll want to pace yourselves if you’re planning a full night out.

This experience is ideal for history lovers, party-goers, groups celebrating special occasions, or anyone intrigued by pirates and the golden age of piracy. It’s especially suited for travelers who appreciate storytelling, local ambiance, and a chance to socialize while learning about the city’s past.

Key Points

• Authentic Pirate Tales: Learn why pirates targeted St. Augustine and how the Spanish countered pirate threats.
• Historic Venues: Visit local pubs that have their own stories and atmospheres, perfect for a relaxed social experience.
• Expert Guides: Knowledgeable guides make the stories engaging and authentic, adding value to each stop.
• Flexible and Fun: Costumes are encouraged but not required; a lively, humorous atmosphere is guaranteed.
• Includes Walking & Drinking: A combination of easy walking and time to enjoy drinks in historic settings.
• Good for Groups: Ideal for celebrations like birthdays, bachelor/bachelorette parties, or just a group of friends looking for fun.

Imagine wandering through the charming streets of St. Augustine, the nation’s oldest city, with a knowledgeable guide sharing true tales of pirates, privateers, and infamous rogues. During the two-hour experience, you’ll hop between some of the best local pubs, each with its own character and history.

The tour begins at the Ponce de Leon Statue near Plaza de la Constitucion, where you’ll check in and meet your guide. From there, the journey unfolds at a relaxed pace, giving you plenty of time to enjoy your drinks, soak up the atmosphere, and listen to stories that are as salty as the ocean itself.

You can check availability for your dates here:

The Stops and Stories

Each pub stop offers a different slice of pirate history and local lore. As you sip your drink, your guide will recount why pirates targeted St. Augustine, especially because of its strategic location and wealth. You’ll discover how Spanish defenders fought back, with stories of fortresses and daring raids.

One highlight is hearing about Castillo de San Marcos, which served both as a fortress and a prison for notorious pirates and criminals. The tales of scandal and mutiny embedded in the city’s streets make the experience lively and memorable.

The Atmosphere and Ambience

The venues chosen are steeped in history and charm, with many dating back centuries. Expect a cozy, rustic vibe perfect for imagining pirates’ hideouts and taverns of the past. The group size remains intimate enough to foster good conversation, and the guides’ storytelling is lively, humorous, and packed with authentic details.

The Drinks and Costumes

While alcoholic beverages are not included in the price, you’ll have plenty of opportunities to enjoy drinks that fit the pirate theme—beers, cocktails, or mocktails. Costumes are encouraged but not mandatory, adding to the fun and photo opportunities.

The Tour’s Practicalities

At just $35, this tour offers a strong value for the experience it delivers—especially considering the stories, guide expertise, and the atmosphere. It lasts about 2 hours, usually in the evening, making it a perfect start or supplement to an evening out in St. Augustine.

The tour is suitable for adults 21 and over, and participants are advised to wear comfortable shoes for the walking portions. Be sure to bring ID and a sense of adventure.

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The Guide’s Role and Guest Experience

Guests consistently praise the knowledgeable guides for their storytelling abilities and sense of humor. One reviewer mentioned, “Our guide was fantastic—full of stories and kept us entertained the whole time.” This highlights how much guides bring to the experience, combining facts with fun.

Since the tour is a walking pub crawl, it’s important to note that people with mobility issues might find it challenging, as it involves some walking and standing. Still, the relaxed pacing and engaging stories make it accessible for most.

Final Thoughts: Is It Worth It?

If you enjoy history, local lore, and a bit of boisterous fun, this pub crawl is a great way to get a taste of St. Augustine’s pirate past without a long commitment. It’s perfect for groups celebrating special occasions or solo travelers eager to meet others in a lively setting.

The tour’s focus on storytelling, combined with authentic venues and expert guides, creates an experience that’s both educational and entertaining. For just $35, you get an evening filled with salty tales, historic ambiance, and a chance to learn about the city’s legendary pirates.

Who Should Book This Tour?

This experience is best for adults who enjoy a mix of history and socializing. It’s ideal for those interested in pirate lore, local traditions, or simply looking for a fun, relaxed night out. Travelers seeking a more active or family-friendly experience might find this tour less suitable, as it’s geared toward an adult crowd and involves alcohol.

Final Advice

Plan ahead: wear comfortable shoes and consider bringing a camera for photos in the atmospheric streets. Arrive on time at the meeting point to avoid missing out on the initial stories and to get the most from your two hours of fun.

The Pirates and Privateers Pub Crawl offers a lively and authentic look at St. Augustine’s pirate history through engaging storytelling and a great local atmosphere. It’s a fun, affordable way to spend an evening in this historic city—whether you’re a history buff, a party enthusiast, or just someone looking to add a little adventure to your trip.

Is the tour suitable for children?
No, the tour is only for adults 21 and over because alcohol consumption is part of the experience.

Are alcoholic drinks included in the price?
No, drinks are not included, but you will have the opportunity to purchase beverages at each pub stop.

How long does the tour last?
The pub crawl lasts approximately 2 hours, usually in the evening.

Where do I meet the guide?
Check-in is at the Ponce de Leon Statue next to the Plaza de la Constitucion.

Do I need to wear costumes?
Costumes are encouraged but not required, adding to the fun and photo opportunities.

Is this tour accessible for people with mobility issues?
It involves walking and standing, so it may not be suitable for all mobility-impaired travelers.

What should I bring?
Bring a valid ID or passport, comfortable shoes, and your sense of adventure.

Can I cancel?
Yes, you can cancel up to 24 hours in advance for a full refund.

How much does the tour cost?
It costs $35 per person, offering good value considering the storytelling and local atmosphere.

This tour strikes a balance between history, fun, and socializing, making it a memorable way to explore St. Augustine’s pirate past. Whether you’re a dedicated history nerd or just in the mood for a lively night out, it’s worth considering for your visit.

You can check availability for your dates here: