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

Explore the intriguing underground stories of St. Augustine with Spyglass Travel's Wicked St. Augustine: Bootleggers, Brothels & Gambling in the Ancient City walking tour. This private experience offers an immersive journey through the city’s rebellious past, revealing hidden speakeasies, secret gambling halls, and colorful characters from the Prohibition era. As you stroll through historic districts, guides share captivating tales of illicit activity, local legends, and the city’s role in early American history. Perfect for history buffs and adventure seekers alike, this tour combines storytelling with picturesque scenery, making it an unforgettable way to uncover St. Augustine's vibrant past. Whether you're fascinated by the lawless days of the early 20th century or eager to explore historic districts off the beaten path, this experience is designed to entertain and educate in equal measure. Comfortable walking shoes are recommended, and your guide will ensure a safe, engaging exploration of the city's lesser-known stories that bring history to life. Join Spyglass Travel for a private adventure that reveals how St. Augustine became the beacon of both beauty and mischief in Florida's oldest city.