If you’re wandering through the charming streets of St. Augustine and craving a fun, educational experience that appeals to all ages, the Family Friendly Pirate Tour promises exactly that. Though we haven’t personally taken this tour, the glowing reviews and detailed itinerary paint a picture of an engaging, well-rounded adventure centered around the legendary pirates of the American coast.
What immediately excites us about this experience are its focus on authentic pirate stories and the interactive approach that makes history lively and accessible. The tour’s emphasis on off-the-beaten-path exploration ensures you’ll see parts of the city most visitors might miss, all while enjoying a relaxed pace suitable for families. A potential consideration? Since it’s a walking tour, comfortable shoes are a must, and snacks or water are recommended — no food or drinks are included.
This experience appears tailored for families, history buffs, or anyone who enjoys a good story, a bit of adventure, and exploring the lively streets of St. Augustine with a knowledgeable guide. Whether you’re traveling with kids or simply want a fun twist on history, this pirate-themed outing offers plenty of value amid its modest price point.
Key Points

- Authentic Pirate Stories: Learn true tales from the Golden Age of Piracy, including attacks on the city and first-hand accounts.
- Family Friendly: Designed for all ages, making it ideal for families or groups wanting a relaxed, engaging experience.
- Compact and Walkable: The tour lasts approximately 1 hour 30 minutes, covering key historic sites on foot.
- Rich Local Context: Visits include the Castillo de San Marcos and the lively St. George Street — essential sights with pirate twists.
- Expert Guide: The reviews highlight guides like Greg, who bring history to life with fun facts and a true local’s passion.
- Affordable: At $33 per person, it offers good value for a well-curated, storytelling-rich experience.
An Insight into the Tour Experience

The Family Friendly Pirate Tour weaves together history, storytelling, and a bit of adventure, making it a standout among the many ways to explore St. Augustine. Its 1.5-hour format strikes a balance between being manageable for kids and engaging enough for adults, making it an ideal family outing.
Starting Point and Meeting Location: You’ll gather at 2 Cuna Street, a convenient spot within the historic district. The tour concludes near the Governor’s House Cultural Center, allowing for easy exploration afterward, whether you want to continue wandering or grab a bite.
You can also read our reviews of more tours and experiences in St Augustine.
The Itinerary: A Step-by-Step Look
Castillo de San Marcos:
The tour begins at this oldest masonry fort in the continental U.S., built by the Spanish in 1672. Its coquina stone walls withstand centuries of attacks, serving as a tangible reminder of the city’s strategic importance. Your guide will tell stories of pirates and soldiers who fought here, sharing tales that bring the stones to life. Expect to hear about legendary raids, and possibly even discover how pirates used the river and fort in their escapades.
Plaza de la Constitución:
Next, the group moves to the heart of St. Augustine—the oldest public square in the U.S., dating back to 1573. It’s surrounded by colonial architecture that has witnessed centuries of change. Here, stories of Spanish colonists, pirates, and local legends deepen your understanding of how this city became a pirate hotspot. The lively atmosphere of the square makes it easy to imagine how pirates might have lurked nearby, waiting to seize treasure ships.
Matanzas River:
Pirates once prowled these waters, drawn by Spanish treasure ships and the city’s key port position. The guide will share tales of notorious raiders such as Sir Francis Drake and other pirates who used this waterway to attack and escape. The river’s quiet beauty today belies its turbulent past as a playground for pirates and privateers alike.
St. George Street:
The tour concludes on this bustling street, where history meets modern life. Once a colonial thoroughfare, it’s now packed with shops, cafes, and historic buildings. As you stroll, you’ll hear stories of pirates, colonial traders, and the city’s role during the Golden Age of piracy. It’s the perfect spot for a snack or souvenir shopping.
What’s Included and What’s Not
Included:
- Guided tour — a knowledgeable guide will lead you through the city’s pirate past and present.
Not Included:
- Snacks or drinks — you’ll need to bring your own if you want to nibble along the way. Luckily, there are plenty of eateries nearby for a quick break before or after.
Practical Details

This tour uses a mobile ticket system, making it easy to book and show up. With a maximum group size of 15, it remains intimate enough for questions and personalized storytelling. The price of $33 per person is quite reasonable considering the depth of stories and sights covered.
Timing and Accessibility:
Starting at 2 Cuna Street, the tour lasts about 90 minutes, making it suitable for most visitors. It’s a walking tour, so comfortable shoes are a must, especially given the historic cobblestones. Since the tour is near public transportation and accepts service animals, accessibility shouldn’t be a major issue.
What Past Participants Say

The sole review available is glowing: “This is by far the best tour in St. Augustine! It is far better than the made-up ghost tours that don’t offer much substance. Greg is so much fun and knowledgeable! Our whole group had a great time. This tour is led by a true local who loves the city and its history.” This kind of enthusiasm suggests guides like Greg bring real passion and storytelling flair to the experience, greatly enriching the visit.
Analyzing the Value

At $33 per person, the tour offers a compelling mix of entertainment and education. It’s affordable, especially given the engaging stories and historic sites visited. While it doesn’t include food or drinks, the proximity to eateries makes it easy to extend your experience with local cuisine. Considering the personalized touch and small group size, this tour offers excellent value for families, history fans, or anyone looking for a fun, authentic way to explore St. Augustine’s pirate past.
The Sum Up

The Family Friendly Pirate Tour in St. Augustine combines history, storytelling, and local charm into a manageable, engaging package. Its focus on genuine pirate stories and the knowledgeable guides make it stand out as a lively, educational experience suitable for all ages. Visitors will appreciate the compact itinerary that covers major historic sites with a pirate twist, all at a reasonable price.
This tour is especially attractive for families or groups seeking a relaxed, fun way to learn about the city’s past without the noise or gimmicks of some other attractions. The small group size and interactive approach ensure everyone feels involved, making it more than just a walk — it’s a storybook adventure that brings St. Augustine’s pirate days back to life.
For those looking to combine a sense of history with a bit of fun and adventure, this tour hits the mark. It’s a chance to walk in the footsteps of pirates, explorers, and soldiers, gaining a deeper appreciation for a city that’s been shaped by legends of the sea.
FAQ

How long is the tour?
It lasts approximately 1 hour 30 minutes, making it a manageable activity for most visitors.
Where does the tour start and end?
It begins at 2 Cuna Street and finishes near the Governor’s House Cultural Center at 48 King Street.
Is it suitable for children?
Yes, it’s designed to be family friendly and suitable for all ages interested in pirate stories and local history.
Do I need to bring anything?
Comfortable shoes are recommended, and bringing water and snacks is advised as no food or drinks are provided.
How many people are in a group?
The maximum group size is 15 travelers, ensuring a more personal, engaging experience.
What if I have mobility issues?
Since it’s a walking tour, comfortable shoes are essential, but the tour’s accessibility will depend on individual needs — contact the provider if you have specific concerns.
Can I cancel or reschedule?
Yes, free cancellation is available up to 24 hours before the tour. Refunds are processed if canceled in time.
Are service animals allowed?
Yes, service animals are permitted on the tour.
Is the tour weather-dependent?
Yes, the tour requires good weather. If canceled due to bad weather, you’ll be offered a rebooking or full refund.
In summary, the Family Friendly Pirate Tour offers an authentic, lively, and educational peek into St. Augustine’s pirate past. With engaging storytelling, a small-group atmosphere, and a reasonable price, it’s a fine choice for families, history buffs, or anyone wanting a memorable city adventure rooted in the legendary days of piracy.
More Tours in St Augustine
More Tour Reviews in St Augustine
Not for you? Here's more nearby things to do in St Augustine we have reviewed
- Haunted in Pink Ghost Tour
- Fun Scavenger Hunt in St. Augustine
- Family Friendly Pirate Tour
- St. Augustine Historical FOOD Tour on Electric Cart with Pick Up
- Art of the Gilded Age
- Ghoul Night Out Haunted Pub Crawl in St. Augustine
- Saint Augustine Ghost Tour
- St Augustine, Florida: Mystic Tour Experience
- St Augustine History and Cheesecake Golf Cart Tour
- Dolphin and Nature Boat Excursion
- St Augustine Side Streets and Secrets Tour
- St. Augustine Champagne Sunset Cruise w Seasonal Nights of Lights
