If you’re looking to add a splash of pirate adventure to your trip in Florida, the St. Augustine: Pirates and Privateers Pub Crawl might just be the right choice. While I haven’t personally been on this tour, it’s a popular option for those wanting to combine history, fun, and a few drinks while exploring the oldest city in the U.S.

What I like about this experience is how it promises engaging storytelling from knowledgeable guides and a chance to enjoy some of St. Augustine’s most atmospheric taverns. Plus, with the option to dress up in pirate gear (costumes are encouraged but not required), it adds a playful, immersive touch.

One thing to keep in mind is that this is a walking tour with some drinking involved, so it’s not ideal if you have mobility issues or prefer more relaxed, sit-down experiences. It’s best suited for those who enjoy lively, interactive outings and have a sense of humor about the whole pirate theme. If you love history mixed with a little spirited fun, this tour could be a highlight of your visit.

Key Points

Fun and Educational: A lively mix of storytelling about pirates, privateers, and St. Augustine’s strategic defenses.
Includes Local Stops: Multiple pub visits give you time to relax, chat, and sample drinks in atmospheric surroundings.
Guided by Knowledgeable Experts: Guides are praised for their engaging, informative storytelling.
Cost-Effective: At $35 per person for two hours, it offers good value for a mix of history, fun, and socializing.
Not Kid-Friendly: Suitable for those 21 and over; not designed with families or mobility-impaired travelers in mind.
Flexible Payment & Cancellation: Book now, pay later, with full refunds available if canceled 24 hours in advance.

You can check availability for your dates here:

An In-Depth Look at the Pirate Pub Crawl

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Starting Point and Check-in

The adventure begins at the Ponce de Leon Statue near the Plaza de la Constitucion. It’s easy to find, right in the heart of historic St. Augustine. Meeting your guide here sets the tone for a relaxed, friendly experience that feels more like hanging out with friends than a formal tour.

The Route and Stops

The tour spans approximately two hours, typically in the evening, which allows you to enjoy the city’s charming streetlights and cobblestones. As you walk between pubs, your guide shares stories about why pirates targeted St. Augustine, including its strategic position and valuable treasure, as well as how the Spanish fought back to protect their holdings.

Each pub stop is thoughtfully chosen to provide a taste of local ambiance, with enough time to order a drink and soak in the atmosphere. Some reviews mention that the stops aren’t just about drinking—they’re about understanding the city’s colorful history and pirate legends. The guides tend to be very knowledgeable, often sharing interesting anecdotes, such as the fact that Castillo de San Marcos was both a fortress and a prison for notorious pirates and rogues.

The Guides: Why They Matter

Guests consistently praise the guides for their enthusiasm and deep knowledge. One reviewer notes, “Our guide was incredibly engaging, blending humor with historical facts seamlessly.” This makes the storytelling more lively and memorable, especially if you’re a history buff or simply enjoy good narratives.

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The Experience and Atmosphere

The vibe is informal, and costumes are encouraged—though not mandatory. Imagine walking the historic streets dressed as a pirate, trading tales with fellow travelers, and raising a glass or two in historic pubs. The atmosphere is fun, a little cheeky, and definitely relaxed. Expect plenty of laughs, some pirate slang, and a chance to learn about infamous figures like Blackbeard and Robert Searles.

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Drinking and Value

Since alcohol isn’t included in the ticket price, you’ll want to budget for drinks at each pub. But this allows you to choose what you like, whether that’s a local beer, a cocktail, or perhaps a soft drink if you prefer. For $35, you’re paying for the storytelling, guided experience, and access to some of the best spots in town—adding your own drinks makes it a flexible, personalized outing.

What Guests Say

Travelers appreciate the value for money and the informative guides. One reviewer mentions, “It was a fun way to see the city and learn some pirate lore without feeling like a museum tour.” Another highlights that it’s perfect for groups celebrating birthdays or bachelor/bachelorette parties, thanks to its lively and social nature.

Considerations and Downsides

This tour isn’t suitable for everyone. It’s not recommended for children under 21 or those with mobility difficulties. Also, if you’re not a fan of walking or standing for two hours, this might not be the best fit. Some reviews suggest that the pace is leisurely, but it’s still a walking tour with some standing. Also, since gratuities are not included, be prepared to tip your guide if you enjoyed the experience.

Practical Information

Price: $35 per person for a 2-hour guided pub crawl
Duration: Usually in the evening, about 2 hours long
Meeting Point: Ponce de Leon Statue near Plaza de la Constitucion
What to Bring: ID or passport, comfortable shoes, and your sense of adventure
What’s Not Included: Alcoholic beverages (you buy those), gratuity for your guide
Booking & Cancellation: You can reserve now with the option to pay later; cancel up to 24 hours in advance for a full refund

Is It Worth It?

For those interested in history, pirates, or just having a fun night out in St. Augustine, this tour offers a playful yet informative experience. The guides’ reputation for being knowledgeable ensures you’ll come away with genuine stories that bring the city’s past to life. Plus, the atmosphere in historic pubs adds a layer of authenticity and coziness you won’t find in more sanitized tours.

However, if drinking isn’t your thing or you prefer a more relaxed, non-walking experience, this might not be ideal. It’s also worth considering how much you value guided storytelling versus self-exploration. But if you’re game for a spirited, social adventure that combines history and humor, this pub crawl is a good pick.

Who Is This Tour Best For?

This experience suits adventure-loving groups, singles, or couples looking to have fun while learning about pirate lore. It’s particularly good for people celebrating special occasions or those wanting a lively night with a historical twist. Since costumes are encouraged, it’s also a good choice if you enjoy dressing up and making the experience more immersive.

It’s not geared toward families or travelers with mobility challenges, but for those who enjoy social, guided explorations with a bit of a cheeky pirate vibe, it ticks a lot of boxes.

FAQ

How long is the pub crawl?
It lasts approximately 2 hours, usually in the evening, allowing plenty of time to explore and socialize.

Do I need to dress up?
Costumes are encouraged but not required. Wearing pirate gear can make the experience more fun, but you won’t be penalized if you don’t.

Are drinks included?
No, drinks are not included. The ticket covers the tour and guides, so you’ll need to buy your own beverages at each pub.

Is this suitable for children?
No, this tour is only for guests aged 21 and over due to alcohol consumption and the nature of the experience.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours before the tour for a full refund.

Is this tour accessible for people with mobility issues?
No, it’s a walking tour, so participants should be comfortable walking and standing for the duration.

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St. Augustine: Pirates and Privateers Pub Crawl

Final Thoughts

The St. Augustine: Pirates and Privateers Pub Crawl offers a fun, engaging way to discover the city’s pirate past while enjoying some local pubs. The knowledgeable guides, lively storytelling, and atmospheric stops make for an experience that’s both educational and entertaining. It’s best suited for travelers who enjoy social outings, history, and a little playful mischief.

While it’s not a quiet, contemplative tour, it’s a great way to see the city from a different perspective and make some memorable stories of your own. Whether you’re celebrating a special occasion or simply want to add a dash of pirate fun to your trip, this pub crawl is worth considering for an evening of laughs, lore, and local flavor.