Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
Active
1h
For a full refund, cancel at least 24 hours before the scheduled departure time.
Manual confirmation
Mobile or paper ticket accepted
About this experience
The Wicked St. Augustine tour delves into the unwritten history of the nation's oldest city. You will hear stories of the illicit industries that made the town a financial success, all while avoiding the reputation of a sinful city. From its founding St. Augustine had a thriving tavern, gambling and prostitution industry, even while portraying a city founded on religious principles. See the locations of high stakes gambling, speak easy taverns, and private clubs which skirted around the laws of the day, like prohibition. Learn how the political powers knew of these activities, secretly supported their providers, all while keeping a squeaky clean image.
Available options
Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City
What's included
Guided narrative of the illicit activites that took place in the 'family friendly' tourist town'
Detailed itinerary
1
Stop 1
The courtyard in front of the old Alcazar Hotel, now the Lightner Museum, also in full view of the old Ponce de Leon Hotel, now Flagler College.
2
Stop 2
Location of the old Ponce de Leon Hotel, built by Henry Flagler. This was the epitome of luxury and decadence during the Gilded Age.
3
Here the stories of the private clubs that lined this and the adjoining streets, gambling halls, speak easies, and boarding houses for upscale vacationers, to the working men of the city.
4
From here guests will hear stories of gambling halls, speak easies and boarding houses (which were code in the day for brothels).
Available languages
Guide guide
EN
Reviews breakdown
Viator
4.7
30 reviews
5★
24
4★
4
3★
1
2★
1
1★
0
Tripadvisor
4.9
59 reviews
5★
56
4★
2
3★
0
2★
1
1★
0
Important information
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Suitable for all physical fitness levels
Meeting point
Guide will meet guests at the fountain in the front courtyard of the Lightner Museum in between the museum and Flagler College.
About St. Augustine
St. Augustine, Florida, is the oldest continuously inhabited European-established settlement in the contiguous United States, founded in 1565 by Spanish settlers. It's a city rich in history, culture, and charm, offering a unique blend of colonial architecture, scenic waterways, and vibrant arts. Visitors can explore centuries-old fortifications, stroll through historic streets, and enjoy the sunny Florida weather.
Top Attractions
Castillo de San Marcos
This is the oldest masonry fort in the continental United States, built by the Spanish in 1672. It offers a glimpse into the city's colonial past and stunning views of the bay.
Historical
1-2 hours
$10 (adults), Free (children under 15)
St. George Street
A pedestrian-only street in the heart of the historic district, lined with shops, restaurants, and historic sites.
Historical
1-2 hours
Free to explore (costs vary for shops and restaurants)
Flagler College
A former hotel turned college, known for its stunning architecture and rich history. Guided tours are available.
Historical
1 hour
$10 (adults), $5 (children under 12)
Fort Matanzas National Monument
A lesser-known fort built by the Spanish in 1742, offering a quieter and more secluded historical experience.
Historical
1-2 hours
Free (park entry), $3 (ferry to the fort)
St. Augustine Alligator Farm Zoological Park
A unique zoo featuring a variety of animals, including alligators, birds, and reptiles. It's also one of the few places where you can see all 24 species of crocodilians.
Nature
1-2 hours
$25 (adults), $15 (children 3-12)
Fountain of Youth Archaeological Park
A historic park that claims to be the site of the legendary Fountain of Youth. It offers a mix of history, archaeology, and natural beauty.
Historical
1-2 hours
$15 (adults), $10 (children 7-12)
Must-Try Local Dishes
Conch Fritters
Deep-fried fritters made from conch meat, often served with a spicy dipping sauce.
Appetizer
Contains seafood
Grouper Sandwich
A fresh grouper fillet served on a bun, often with lettuce, tomato, and a tangy sauce.
Lunch
Contains seafood, gluten (if served on a bun)
Spanish Bean Soup
A hearty soup made with white beans, sausage, and a variety of spices, reflecting the city's Spanish heritage.
Soup
Contains meat, can be made vegetarian
Key Lime Pie
A classic Florida dessert made with key lime juice, egg yolks, and condensed milk, served in a graham cracker crust.
Dessert
Contains dairy, gluten (if served with a graham cracker crust)
Popular Activities
Kayaking
Paddleboarding
Hiking
Beach lounging
Spa treatments
Scenic walks
Historic site tours
Art gallery visits
Best Time to Visit
February to May
This period offers pleasant weather with warm days and cool nights, making it ideal for outdoor activities and sightseeing. The city is lively with various festivals and events.
15-29°C
60-85°F
Practical Information
Language
- Official: English
- Widely spoken: Spanish
- English: Widely spoken
Currency
US Dollar (USD)
Time Zone
Eastern Time Zone (GMT-5:00)
Electricity
120VV, 60HzHz
Safety Information
Overall Safety Rating: Generally safe
St. Augustine is generally safe for tourists, with low crime rates in most areas. However, as with any destination, it's important to stay aware of your surroundings and take basic precautions.
Important Precautions:
- • Keep valuables secure and out of sight.
- • Use reputable tour operators and taxi services.
- • Be cautious when walking alone at night, especially in less crowded areas.
Getting there
By air
- Jacksonville International Airport • 40 miles (64 km)
- St. Augustine Airport • 5 miles (8 km)
By bus
Greyhound Station in St. Augustine
Getting around
Public transport
The local bus service is affordable and convenient for getting around the city.
Taxis
Available • Apps: Uber, Lyft
Rentals
Car, Bike, Scooter
Neighborhoods
Historic District
Lincolnville
Anastasia Island
Day trips
St. Johns River Cruise
10 miles (16 km) north of St. Augustine • Half day
A scenic cruise along the St. Johns River, offering wildlife viewing and beautiful landscapes.
Guana Tolomato Matanzas National Estuarine Research Reserve
15 miles (24 km) south of St. Augustine • Full day
A nature reserve offering hiking, biking, and wildlife viewing in a pristine coastal environment.
Ponce de Leon's Fountain of Youth Archaeological Park
City center • Half day
A historic park that claims to be the site of the legendary Fountain of Youth, offering a mix of history, archaeology, and natural beauty.
Festivals
St. Augustine Food & Wine Festival • November
Night of Lights • December to January
St. Augustine Film Festival • April
Pro tips
- Visit historic sites early in the morning to avoid crowds and enjoy cooler temperatures.
- Explore the city on foot or by bike to discover hidden gems and scenic spots.
- Try local cuisine at historic restaurants and cafes for an authentic experience.
- Check for special events and festivals during your visit for a unique and memorable experience.
- Respect the environment and follow guidelines when visiting natural areas and protected sites.
From $25
per person
Price varies by option
Secure booking
Free cancellation available
