Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City - Authenticity, Value, and Practical Tips

8 Most Highly Rated City Tours In St Augustine

St. Augustine’s charm isn’t just rooted in its age — it’s found in its streets, stories, and secrets. This city, founded in 1565, is a treasure trove for explorers who love history, spooky tales, or just a good adventure. We particularly like the Walking Tour in North City Cemeteries of St. Augustine for its lively storytelling and walking pace that keeps you active while uncovering spots like Tolomato and Huguenot Cemeteries. Meanwhile, fans of the darker side of history will find Wicked St. Augustine: Bootleggers, Brothels & Gambling offers an eye-opening peek into the city’s illicit past.

Whether you’re intrigued by ghostly tales or interested in pirate lore, St. Augustine truly has a lot to offer. From spooky night tours to engaging scavenger hunts, each experience provides a different way to see and feel the city’s stories. Now, let’s explore what makes each tour stand out.

Quick Overview

St. Augustine offers a variety of city tours tailored to diverse interests. You’ll find historical and ghost tours like the Ancient City Tarot Walk and Ghost Stroll, which blends haunted sites with tarot readings, perfect for thrill-seekers or those interested in the supernatural. For a more lively, culturally rich experience, the Old City Ghosts: Phantom Pirates & Poltergeists Tour brings pirate legends and ghost stories to life after dark.

If you prefer hands-on activities, the Fun City Scavenger Hunt offers a playful way to explore, while Scavenger Hunt: Key To The City combines puzzle-solving with sightseeing. For those looking to enjoy the city on two wheels, the Saint Augustine E-Bike Rental ensures you see a lot without breaking a sweat. Each tour’s unique approach makes it easy to find one that matches your travel style.

1. Walking Tour in North City Cemeteries of St. Augustine

Walking Tour in North City Cemeteries of St. Augustine

This Walking Tour in North City Cemeteries takes you through some of the oldest, most atmospheric burial sites in the city — Tolomato and Huguenot Cemeteries. The tour lasts around 1.5 to 2 hours and costs $25 per person. It’s perfect for history lovers who want to learn about St. Augustine’s founding in 1565 while enjoying a leisurely walk. The guide shares stories that are both spooky and fascinating, bringing to life tales of colonial settlers, pirates, and local legends.

What makes this tour stand out is the focus on Spanish colonial history and the opportunity to see the Oldest Wooden School House. Visitors often comment on how the guide’s storytelling keeps everyone engaged. The tour also includes visits to significant sites like Castillo de San Marcos and Potter’s Wax Museum, offering a well-rounded cultural experience. Since it’s a walking tour, comfortable shoes are a must.

Bottom line: For a mix of history, storytelling, and a good stroll, this tour offers great value and memorable stories. It’s ideal for those with a curiosity about the city’s earliest days.

2. Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City

At number 2, this Wicked St. Augustine tour exposes the city’s less-than-pristine past. For $30, you get about an hour and a half exploring the darker corners of the city’s history — from secret speakeasies to illicit gambling halls. The tour takes you down historic streets like St. George Street, pointing out landmarks like Flagler College and the Lightner Museum as backdrops for stories of crime and corruption.

What makes this tour unique is its focus on the city’s underground activities, including prostitution rings and hidden gambling spots during the Gilded Age. The guide’s lively narration and the walk through the historic district make it an engaging experience. While not a ghost or haunted tour, the stories of political corruption and vice add a compelling layer of intrigue. It’s perfect for travelers who like their history with a twist of scandal.

Guests often say the tour is packed with “interesting and real happenings” and consider it a highlight of their trip. Be prepared for some walking, but no long hikes, making it accessible for most.

Bottom line: If you want to learn about St. Augustine’s seedy side with lively storytelling, this tour offers great value. It’s best suited for history buffs or those curious about the city’s mischievous past.

3. Ancient City Tarot Walk and Ghost Stroll in St. Augustine

Ancient City Tarot Walk and Ghost Stroll in St. Augustine

This Tarot Walk and Ghost Stroll combines haunted sites with an element of divination. For just $27, you’ll spend about 75 minutes to 1.5 hours wandering through the city’s most haunted spots, such as Huguenot and Tolomato Cemeteries, while a guide interprets tarot cards connected to St. Augustine’s spectral past.

What makes this tour distinctive is the tarot reading experience woven into the ghost stories. It’s not just about spooky tales; the guide’s interpretations add a mystical dimension, making the tour feel personal and memorable. The tour’s short length makes it ideal for those with limited time or a preference for an intimate, eerie adventure. You’ll learn about legends of ghost sightings and the history behind the sites in a way that feels both spooky and insightful.

Reviews praise the tour for its “divine connection” and the way it enhances the city’s haunted reputation. This tour is best suited for those interested in ghost stories with a spiritual twist, or anyone curious about tarot’s role in storytelling.

Bottom line: Perfect for supernatural enthusiasts who enjoy a touch of mysticism, this tour offers a unique and immersive experience at a reasonable price.

4. Old City Ghosts: Phantom Pirates & Poltergeists Tour

Old City Ghosts: Phantom Pirates & Poltergeists Tour

For those captivated by pirate legends and ghost stories, Old City Ghosts delivers a lively near-hour adventure. Starting after sunset, the tour explores the streets around St. George Street, sharing tales of pirates, vengeful spirits, and unexplained phenomena. Costing $24 per person, it’s ideal for night owls who want to experience the city’s spooky side.

What sets this tour apart is its focus on pirate lore and ghostly legends. The guide’s storytelling evokes vivid images of buccaneers and ghostly apparitions, making it especially fun for families or groups looking for lighthearted scares. The tour caps at 15 people, ensuring a more personal and engaging experience. You won’t go inside any buildings, but the stories bring the city’s haunted past to life.

Many reviews mention the “great storytelling” and how much they enjoyed the mix of history and legend. It’s a good choice if you want a short, spooky walk that captures the essence of St. Augustine’s haunted reputation.

Bottom line: For a quick, entertaining ghost walk with pirate stories, this tour hits the mark. It’s especially suited to those who enjoy a little after-hours mystery.

5. St. Augustine: Old City World of Pirates Experience

St. Augustine: Old City World of Pirates Experience

This Pirates Experience offers a two-hour walk through the city’s pirate history. It explores the Ponce de León Hotel and Castillo de San Marcos, with stories about the Black Raven Pirate Ship and pirate hideouts. It’s a lively storytelling session designed for those who want to combine history with maritime adventure. The guide shares tales of the city’s notorious pirates and their battles, giving color to the waterfront’s past.

What makes this tour stand out is the focus on the pirate era, with vivid descriptions of ships and pirate hideouts. The two-hour duration allows for a more in-depth exploration than shorter ghost walks, making it a good choice for history fans who like maritime lore. The reviews highlight the “engaging storytelling” and the tour’s ability to bring the city’s pirate past to life.

Ideal for families or history buffs, the tour is priced at $24, offering good value for the length and richness of stories. It provides a fun way to see the city’s waterfront while learning about its most daring characters.

Bottom line: If pirates fascinate you, this tour offers a lively, engaging experience that gives real color to St. Augustine’s maritime history.

6. Fun City Scavenger Hunt in St. Augustine by Zombie Scavengers

Fun City Scavenger Hunt in St. Augustine by Zombie Scavengers

For a playful way to explore, the Zombie Scavengers Hunt offers a self-guided game designed for groups of up to 10 people. Priced at $20 per group, it lasts around an hour and involves solving clues and completing challenges to “survive” a zombie apocalypse. The app directs you through notable sites, encouraging teamwork and quick thinking.

What makes this activity unique is its interactive, game-based format that turns sightseeing into a fun competition. It’s great for families, friends, or colleagues wanting a lighthearted challenge. The challenges cover various city landmarks and encourage you to take photos, find clues, and explore beyond the usual tourist spots. The game is supported by a remote host if you need help, adding reassurance for first-timers.

Reviewers mention how much fun they had “running all over the town,” and that it’s a great way to get kids engaged. It’s not a deep dive into history, but perfect for a relaxed, entertaining afternoon.

Bottom line: This scavenger hunt offers a fun, active way to see St. Augustine and is best suited for groups looking for an interactive experience rather than a traditional tour.

$20.00 per group (up to 10)

7. Scavenger Hunt: Key To The City Scavenger Hunt

Scavenger Hunt: Key To The City Scavenger Hunt

Taking a different approach, the Key to the City Scavenger Hunt is a two-hour challenge at just $10 per group. It involves solving clues and completing challenges as you explore city landmarks and hidden corners. The game promotes teamwork and discovery, making it ideal for families or groups of friends.

This tour emphasizes learning through play, with participants uncovering stories behind landmarks while having fun. It’s a more competitive experience, encouraging you to work together to unlock St. Augustine’s secrets. Since it’s a shorter, two-hour activity, it’s perfect if you want a quick, engaging introduction to the city’s sights.

Reviews are limited but note the “fun and challenging” elements, making it a good choice for those who enjoy puzzles and exploration.

Bottom line: For a budget-friendly, interactive way to discover the city’s highlights, this scavenger hunt is a smart pick—especially for those short on time or traveling with kids.

$10.00 per group (up to 1)

8. Saint Augustine E-Bike Rental City Style

Saint Augustine E-Bike Rental City Style

If cycling appeals to you, the E-Bike Rental provides a flexible and fun way to see the city at your own pace. Starting at $100 per person for a day, the rental includes delivery right to your accommodation. You can choose from folding, fat-tire, or child-carrying bikes depending on your needs.

What makes this option stand out is the freedom it offers. You’re not tied to a set schedule or guide, allowing you to explore landmarks like the historic district, waterfront, and quieter neighborhoods comfortably. The bikes are easy to handle, and you can stop whenever something catches your eye.

This rental is ideal for travelers who enjoy independent exploration and want to cover more ground than a walking tour. It’s especially good if you’re traveling with family and need bikes suited for different age groups or terrains.

While it has no guided commentary, you can combine it with other tours or use a guidebook for a self-led adventure. Just remember, you’ll need a good map or app to maximize your route.

Bottom line: For the active traveler who prefers autonomy, e-biking is a fantastic way to absorb the sights of St. Augustine at your own speed.

$100.00 per person

How to Choose Your Perfect Tour

Choosing the right tour depends on your interests, fitness level, and how much time you want to spend. If you love walking and storytelling, the North City Cemeteries Walking Tour offers a balanced mix of history and scenery. For those intrigued by the city’s illicit past, Wicked St. Augustine provides a vivid glimpse into its shadowy side.

Ghost enthusiasts might prefer the Ancient City Tarot Walk, which combines paranormal tales with tarot readings. Families or groups wanting a more active, game-like experience will enjoy the Zombie Scavenger Hunt, while explorers seeking independence can rent an e-bike for a full day of self-guided adventure.

Consider your budget, how much time you have, and whether you prefer guided storytelling or independent exploration. Booking early is wise, especially in peak seasons, to ensure availability.

Final Thoughts

St. Augustine’s tour options cover a wide range of interests — from spine-tingling ghost stories to lively pirate lore and intriguing scavenger hunts. For a deeply historical experience, the North City Cemeteries Walking Tour provides a great introduction. If you want a bit of everything with a darker twist, the Wicked St. Augustine tour offers a bold look at the city’s underbelly.

For a more mystical journey, the Tarot Walk combines paranormal legends with divination. Families and groups who love interactive fun should consider the Zombie Scavenger Hunt. No matter your style, there’s a tour in St. Augustine ready to bring its stories to life—just remember to book early and dress comfortably.