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

The Dark Side of St. Augustine History

Learn the history of the oldest city’s oldest profession – vice. See how St. Augustine existed, prospered and thrived from this hidden history.

Things To Know

  • Duration: 90 minutes
  • Price: $30

Hosted By

Spyglass Travel

Spyglass Travel is a tour company in St. Augustine, Florida that offers guided historical walking tours and cultural experiences throughout the city’s historic district. Their tours include themed history walks, ghost and paranormal tours, and explorations of lesser-known stories and past eras of America’s oldest continuously inhabited European-established settlement. They also provide self-guided downloadable tours and specialize in field trip planning and educational experiences for schools and groups.

This experience is not booked with Casa de Suenos. For any questions, reach out to this vendor directly.

More Experiences

Starting at $89/guest

4‑Passenger Street Kart Rental

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Starting at $795/guest

ASA 101: Learn to Sail in 2 Days

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Avondale Pairing Tour Experience

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Beer & Bites Craft Tour – Amelia Island

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Starting at $65/guest

Clear Kayak Ecotour – St. Augustine

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Starting at $145/guest

Corks & Forks Food & Wine Tour

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Corks & Forks Strolling Tour – St. Augustine

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DIS – Daytona International Speedway

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Starting at $155/guest

Discover St. Augustine’s Wine & Dine Ride

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Starting at $5/guest

Dolphin & Wildlife Tour – Osprey

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Starting at $149/guest

Dolphin Delight & Nature’s Wonders

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Starting at $25/guest

Eco Boat Tours – BEST NIGHTS OF LIGHTS Combo – SUNSET + NIGHTS OF LIGHTS – 4:30 TO 6 PM

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Starting at $99.99/guest

Electric Moke Golf Cart Rental

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Starting at $45/guest

Exclusive Santa’s Magical Lights Ride in St. Augustine

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Starting at $55/guest

GROUP: NOL Carriage + Wine Ride (PRIVATE PARTY)

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Starting at $135/guest

Historic Brunch Tour in St. Augustine

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Starting at $125/guest

Magic Hideaway

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Starting at $774/guest

Nights of Lights Sparkle Sailing Tour

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Starting at $125/guest

Private St. Augustine Ghost Tour

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Starting at $39/guest

Red Boat Tours – B.Y.O.B. Sunset Cruise

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All Our Guest Rooms

Valencia Room

  • King | 2nd Floor | Jet Tub
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Cordova Room

  • Queen | 2nd Floor | Jet Tub
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Sevilla Room

  • King | 2nd Floor | Jet Tub
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Granada Room

  • King | 1st Floor | Shower
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Saragossa Room

  • Queen | 1st Floor | Jet Tub
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Castillo Room

  • King | 2nd Floor | Shower
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Nieves Room

  • Queen | 1st Floor | Shower
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194 San Sebastian River House

  • Sleeps 6 | Entire Home | 2.5 Baths
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196 San Sebastian River House

  • Entire Home | Sleeps 6 | 2.5 Baths
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198 San Sebastian River House

  • 2.5 Baths | Sleeps 6 | Entire Home
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200 San Sebastian River House

  • 2.5 Baths | Sleeps 6 | Entire Home
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End Of Year Gift Certificate Special Offer Through Dec. 31!

We’re running a special right now! If you buy a $400 gift certificate, we’ll throw in a $100 gift certificate. Give the gift of relaxation this year.
*Offer valid through December 31, 2025. Valid on new GC purchases only. Redeemable toward new reservations made for stays after January 5, 2026.

Buy A Gift Certificate