Pirates and Privateers Cocktail Tour in St Augustine

If you’re curious about St. Augustine’s pirate past but prefer a relaxed, adult-oriented experience, the Pirates and Privateers Cocktail Tour might catch your eye. This tour promises a spirited walk through the city’s most intriguing historic spots, combined with visits to some of its best taverns for a drink or two. Although I haven’t personally been on this tour, I’ve gathered enough details and reviews to give you a clear picture of what to expect and whether it might fit your travel style.

What I really appreciate about this experience are two things: firstly, the focus on a fun, storytelling approach that makes history engaging without feeling like a lecture. And secondly, the chance to visit several historic locations while sharing a drink with fellow travelers. Just keep in mind that drinks are not included in the ticket price, so budgeting for beverages is a good idea. Also, because the tour is limited to around nine guests, it tends to feel more intimate and personalized—ideal for those who enjoy small-group experiences.

However, one consideration to keep in mind is that the tour takes place starting at 9:00 pm, so it’s definitely geared toward evening explorers who enjoy a lively, social vibe. If you’re looking for a daytime historical trek or have young kids in tow, this might not be your best fit. But if you’re keen on combining history, local taverns, and a bit of pirate flair, this tour could be a fun addition to your St. Augustine itinerary.

Who would love this? Adults who enjoy stories, history buffs with a playful side, and anyone looking to add some local pub culture to their trip. It’s especially good if you like small groups, personalized guides, and a relaxed pace.

Key Points

• Focus on pirate and exploration themes for an engaging storytelling experience
• Visit historic landmarks like Castillo de San Marcos and the Oldest Wooden Schoolhouse
• Includes visits to popular taverns with the chance to buy drinks at the last stop
• Small group size (max 9) for a more intimate and flexible tour
• Evening start time makes it ideal for those wanting a lively night out
• Price point of $35 offers good value considering the stops and storytelling

What to Expect from the Pirates and Privateers Cocktail Tour

This tour promises more than just a walk; it’s a chance to step into St. Augustine’s pirate days, with lively stories and historic sites woven into the experience. Starting at 9:00 pm on King Street, you’ll meet your guide and begin your journey through the city’s past and present. The tour spans about two hours and covers a series of notable stops, each with its own story and significance.

Walking the Historic Streets

You’ll spend roughly 15 minutes at each stop, exploring landmarks like Charlotte Street, South Castillo Drive, and the Oldest Wooden Schoolhouse. These locations aren’t just random points on a map—they are carefully selected for their ties to the city’s pirate and exploration history.

For example, at South Castillo Drive, you’ll learn about the infamous pirates and privateers who once prowled these waters, plundering and battling along Florida’s coast. As one reviewer mentioned, the guide (Steve) was “an absolute pleasure and a wealth of knowledge,” making even familiar sights come alive with tales of battles, buried treasures, and sea legends.

Deep Dives into Local Landmarks

Further stops include Casa Reina Taqueria & Tequila, which pays tribute to Queen Joanna of Castile—adding a Spanish royal touch to the pirate theme—and the St. Augustine Sea Wall, symbolizing the city’s resilience against invaders and the relentless tides.

One of the tour’s highlights is the Castillo de San Marcos, a stone fortress that looms large in the city’s history. Here, you’ll learn about its role in defending the city from British and other threats, adding a layer of context to the pirates’ story. The guide’s storytelling really shines at this point, as one reviewer noted, “Bryan was very knowledgeable and made the history come alive.”

Final Stop and Beverages

The tour concludes at Mill Top Tavern and Listening Room, where you can purchase an alcoholic beverage and reflect on the stories told. This offers a relaxed setting to socialize and share impressions from the tour. Remember, drinks are not included in the ticket price, so plan to buy your own if you want a toast or two.

The Overall Experience

The reviews tell us that guides like Steve and Bryan significantly enhance the tour’s appeal. They’re praised for their friendliness, knowledge, and ability to keep the storytelling engaging. One guest said, “Hes very knowledgeable! Had a blast!” which sums up the general vibe—informative yet relaxed, with a friendly touch.

The price of $35 is quite reasonable for a two-hour guided experience combining history and lively tavern visits. Considering the small group size and personalized approach, it feels like good value, especially for those who enjoy storytelling, history, or just a good night out with a theme.

The Itinerary in Detail

• Charlotte Street: This initial stop sets the tone, immersing you in the pirate era with stories of plunder and high seas adventures. It’s a quick, free stop but crucial for context.
• South Castillo Drive: Here, you’ll hear tales of the most feared pirates and privateers, contrasting their brutality with the city’s charm today.
• Oldest Wooden Schoolhouse: A real treat for history buffs, this 200-year-old building offers a glimpse into early American education, adding depth to your understanding of the city’s past.
• Casa Reina Taqueria & Tequila: Beyond the pirate theme, this spot pays homage to early Spanish explorers and royalty, broadening the historical scope.
• St. Augustine Sea Wall: An iconic structure, it’s a symbol of the city’s resilience against the sea and invasions.
• Avenida Menendez: Discover stories of a military leader defending the city under Spanish rule, adding a layer of colonial history.
• Castillo de San Marcos: The fortress is a highlight, with tales of defenses and battles that shaped the city.
• Mill Top Tavern: The final stop where you can unwind, buy a drink, and chat about the tales told.

Practical Details You Should Know

The tour begins at 9 King Street, and the route might vary depending on the day, but it typically ends at Mill Top Tavern, located at 19 1/2 St. George Street. With a maximum of nine travelers, it’s a small-group experience that encourages interaction and personalized attention.

Since drinks are not included, you should plan to purchase something at the last stop if you want to toast your journey. The tour is suitable for adults 21 and over, and most travelers can participate, making it a solid choice for anyone interested in history, storytelling, and a casual night out.

Final Thoughts: Is it Worth It?

If you’re in St. Augustine and looking for a fun way to learn about its pirate past while enjoying some local taverns, this tour hits the mark. It’s particularly appealing if you enjoy small groups, engaging guides, and stories that make history feel alive. The moderate price point and positive reviews about knowledgeable guides make it a worthwhile addition to your evening plans.

However, it’s important to note that this is an evening activity, so if you’re after daytime sightseeing or traveling with children, this might not be ideal. It’s best suited for adults who appreciate a mix of history, storytelling, and social drinking—especially those who want to keep their night light and lively.

FAQs

Is this tour suitable for children or families?
This tour is designed for adults 21 and over, mainly because alcohol is involved. It’s a night-time experience with a focus on taverns, so it’s best suited for adults.

How long does the tour last?
The tour lasts about 2 hours, covering several historic stops in the city.

Are drinks included in the price?
No, drinks are not included. You’ll have the opportunity to purchase beverages at the final stop.

Do I need to book far in advance?
It’s advisable to book ahead, especially since the tour has a cap of 9 guests. Confirmations are received immediately upon booking.

Is the tour wheelchair accessible?
This detail isn’t specified, but since it involves walking and outdoor stops, it’s best to contact the provider if accessibility is a concern.

What should I wear?
Comfortable shoes and weather-appropriate clothing are recommended. The tour takes place outdoors, so dress for the evening weather.

Can I cancel or reschedule?
Yes, there’s free cancellation up to 24 hours in advance. Cancellations within 24 hours are non-refundable.

What’s the guide’s role?
Guides like Steve and Bryan are praised for their knowledge and friendly demeanor, making the stories come alive and ensuring a fun experience.

How many stops are there?
There are eight stops, each about 15 minutes long, covering a mix of historic sites and taverns.

This Pirates and Privateers Cocktail Tour offers a lively, story-driven way to explore St. Augustine’s pirate days while enjoying the city’s tavern scene. It’s perfect for adults who want a relaxed, social evening with a good dose of history and fun stories. If that sounds like your kind of night out, it might just be the highlight of your visit.