Introduction

If you’re seeking a lively, informative way to explore St. Augustine’s legendary pirate past, the Pirates and Privateers Walking Tour offers a captivating experience without breaking the bank. This tour promises a blend of engaging storytelling, historic sights, and scenic views, all led by knowledgeable guides who know how to keep the stories fun and authentic.
What we especially like about this tour is its short, manageable duration of around 90 minutes, making it an ideal activity for families or travelers with busy schedules. The scenic stops at key historic sites really bring the city’s pirate lore to life, and the enthusiastic guides often share insider tidbits that you won’t find in guidebooks. You’ll also appreciate how the tour combines history with a dash of humor, making it both educational and entertaining.
A potential consideration is that it’s a walking tour, so comfort in walking shoes is recommended—there’s no transportation involved. Also, some stops require separate admission fees if you wish to explore further, which is worth noting for those on a tight budget.
This experience is best suited for history enthusiasts, families with children who enjoy stories of pirates, and anyone curious about St. Augustine’s storied past. It’s also a good pick for travelers who enjoy walking tours that combine storytelling with scenic sightseeing.
Good To Know
- Affordable price point at $24.99 per person for a 1.5-hour adventure.
- Engaging guides that share lively tales and insider insights.
- Multiple historic stops that highlight the city’s pirate, native, and colonial history.
- Comfortable walking pace with manageable stops that fit most schedules.
- Includes free admission to some sites and optional paid visits.
- Ideal for families and history buffs seeking a fun, educational experience.
Interested in exploring St Augustine on foot? Other walking tours we've covered
A Closer Look at the Tour Itinerary

Starting Point at Ghost City Tours of St. Augustine
Your adventure begins at the Ghost City Tours shop on 9 King St, where you can pick up tour merchandise, umbrellas, or refreshments before setting out. This initial stop ensures you’re well-prepared for the walk ahead, especially considering Florida’s unpredictable weather.
The staff here are friendly and organized, making the start smooth and hassle-free. It’s worth arriving a bit early, especially if you want to browse the souvenirs or grab a quick drink. The meeting point’s central location also makes it easy to find, whether you’re arriving via local transit or walking from nearby accommodations.
Castillo de San Marcos National Monument
Next, you’ll visit Castillo de San Marcos, the oldest masonry fort in continental U.S. It’s a striking sight, with its coquina stone walls and historic cannons. Here, guides share stories about Native Americans of the Timucuan tribe and a famed Spanish sea captain, adding layers to the fort’s significance.
While admission to the castle isn’t included, the stop offers plenty of photo opportunities and interesting facts that help set the scene for pirate activity in the area. You might find yourself imagining pirate ships approaching the harbor while overlooking the St. Augustine waterfront. The 15-minute visit is just enough to pique your curiosity without feeling rushed.
Ponce de Leon Statue at 1 Anderson Cir
This stop is a favorite for many—it’s where you can see the statue of Ponce de Leon, the legendary explorer linked to the search for the Fountain of Youth. The guide will recount his adventures in St. Augustine, emphasizing the legend and the historical context.
You’ll love the views here, often framed with historic buildings and lush surroundings. It’s a brief stop, but a memorable one that connects the city’s mythic past with real exploration. And it’s free, which makes it a practical addition to your tour.
Governor’s House Cultural Center and Museum
This stop offers a deeper dive into Native American history, particularly the Yamasee tribe, and the city’s role in the Underground Railroad. The guide will also tell the story of a pirate who rose from slavery, highlighting the complex social history of the area.
Admission isn’t included, but the site is worth exploring if you’re interested in the layered history of St. Augustine beyond just pirates. The stories told here add depth and context, enriching your understanding of the city’s diverse past.
St. Augustine Sea Wall
Next, the tour moves to the historic sea wall, a vantage point where you can see the port and harbor. Guides talk about the frequent pirate conflicts—Spanish and British privateers who fought over control of the waters.
This stop is particularly engaging because of the palpable sense of history and the stunning views. You might even keep an eye out for ships entering the harbor, adding a dash of maritime suspense to the experience. It’s a free stop, offering both scenic beauty and historical insight.
No Name Bar and Pirate Haunts
The final stops are at the No Name Bar, a location with a notorious past, and stories of pirates with no names. The guide shares tales of infamous pirates and the shadowy corners of old St. Augustine’s nightlife.
Although the bar itself isn’t part of the tour, the stories about it make for a fun, slightly mischievous ending. Some of the sites are free to view, but the bar is an example of the local lore that makes this tour memorable.
The Experience and Guides

Throughout the tour, you’ll be accompanied by knowledgeable guides—often locals or historians—who keep the storytelling lively and engaging. They’re skilled at balancing historical facts with entertaining anecdotes, making history accessible for all ages.
The reviews mention that guides are “amazing,” “fun,” and full of insider stories that you can’t find in books. Their enthusiasm and storytelling ability help bring the city’s pirate past to life, making the walking tour feel like a mini adventure rather than a dry history lesson.
Value and Practicalities

At $24.99 per person, this tour offers good value for a scenic, educational experience in the heart of St. Augustine. The 1.5-hour format is suitable for most schedules, especially those wanting a quick but enriching activity.
The tour’s group size is capped at 25, ensuring a more intimate experience where questions are encouraged. Plus, the mobile ticket system streamlines entry, so you don’t have to worry about paper tickets.
It’s worth noting that the tour begins at 7:00 pm, making it a fantastic option for those who want to explore after daytime activities or enjoy the city’s evening ambiance. The tour ends just a short walk from the start point, making it convenient to continue exploring or dine in nearby spots.
Weather and Cancellation Policies
Since the tour is outdoor-focused, good weather is important. If canceled due to rain or storms, you’ll be offered a different date or a full refund. Cancellations more than 24 hours in advance are fully refundable, offering peace of mind for travelers planning ahead.
Final Thoughts

The St. Augustine Pirates and Privateers Walking Tour delivers a fun, balanced blend of history, storytelling, and scenic views in a manageable timeframe. It’s perfect for families, history lovers, or anyone curious about the city’s notorious past. The guides’ engaging storytelling, combined with stops at iconic sites, makes for a memorable experience that brings the city’s pirate heritage alive.
While it’s a walking tour—so comfortable shoes are a must—the overall value for the price and the authentic tales make it a worthwhile addition to your St. Augustine itinerary. Whether you’re a seasoned history buff or seeking a family-friendly adventure, this tour offers a charming glimpse into one of Florida’s most storied ports.
FAQ

Is the tour suitable for children?
Yes, the tour is family-friendly, and children who enjoy pirate stories typically find it engaging.
How long does the tour last?
It lasts approximately 1 hour and 30 minutes, making it a perfect quick yet enriching activity.
Do I need to make a reservation?
Booking in advance is recommended as the tour has a maximum of 25 travelers, but the ticket is mobile for easy access.
Are there any additional costs?
Some stops include admission fees if you choose to explore further, but the tour itself covers many key sights at the listed price.
What should I wear?
Comfortable walking shoes are advisable, and bring an umbrella or poncho in case of rain.
Does the tour include transportation?
No, it is a walking tour, so you’ll be on foot throughout the approximately 90-minute experience.
What time does the tour start?
The tour begins at 7:00 pm, providing a lovely evening stroll.
Is the tour accessible for service animals?
Yes, service animals are allowed, and the tour is near public transportation.
What happens if the weather is bad?
If canceled due to weather, you’ll be offered a different date or a full refund.
Can I cancel my booking?
Yes, cancellations are free if made more than 24 hours in advance; within 24 hours, no refund is issued.
Final Words

This walking tour offers a lively, accessible way to explore St. Augustine’s pirate history, combining scenic spots with engaging storytelling. It’s ideal for those wanting a short, informative, and fun activity that fits well into a busy day or evening schedule. The guides’ passion and knowledge bring the city’s seafaring past back to life, making it a highlight for many visitors.
For travelers eager to learn about pirates, explore historic sites, and enjoy the unique charm of St. Augustine, this tour delivers genuine value without the hefty price tag. Just remember to wear comfortable shoes, arrive a little early, and prepare for an adventure filled with tales of treasure, ships, and swashbuckling characters.
More Walking Tours in St Augustine
More Tours in St Augustine
- Historic District Brunch Tour (St. Augustine)
- Guided Salt Marsh Kayak Tour
- Red Boat Tours – BYOB Sunset Cruise on St. Augustines Waterway
- Red Boat Tours – Dolphin Odyssey and Sightseeing Tour
- St. Augustine Ghost Tour on Premium Golf Cart with PiCk Up
- St Augustine Haunted History: A Self-Guided Audio Tour
More Tour Reviews in St Augustine
- Historic District Brunch Tour (St. Augustine)
- Guided Salt Marsh Kayak Tour
- Red Boat Tours – BYOB Sunset Cruise on St. Augustines Waterway
- Red Boat Tours – Dolphin Odyssey and Sightseeing Tour
- St. Augustine Brunch on the Bay with Drinks and Light Bites
- St. Augustine Ghost Tour on Premium Golf Cart with PiCk Up
Looking for something different? Other St Augustine activities we've written about
- Historic District Brunch Tour (St. Augustine)
- Guided Salt Marsh Kayak Tour
- Red Boat Tours – BYOB Sunset Cruise on St. Augustines Waterway
- Red Boat Tours – Dolphin Odyssey and Sightseeing Tour
- St. Augustine Brunch on the Bay with Drinks and Light Bites
- St. Augustine Ghost Tour on Premium Golf Cart with PiCk Up
- St. Augustine Live Music Sunset Sail and Fireworks July 4th Only
- St Augustine Haunted History: A Self-Guided Audio Tour
- St. Augustine Night of Lights Cruise with Live Music and Drinks
- Oracle of St. Augustine, Messages from the Universe.
- St. Augustine 6 Passenger Unique Moke Golf Cart Rental
- Self Guided Audio Tour of St Augustine’s Twisted History
