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Offered languages
- English
Step into the shadows of Portland’s past on this thrilling true crime tour, where secrets lurk behind historic facades and cobblestone streets whisper tales of corruption, violence, and vice. From ruthless mobsters and bootleggers to power-hungry bosses and shocking scandals, this tour unveils the darker side of Maine’s largest city. Walk the very streets where speakeasies thrived, deals were made in the dead of night, and blood was spilled in the name of power. Led by expert guides, this journey through Portland’s underworld will leave you with spine-tingling stories you won’t soon forget. Dare to explore the city’s past? Book now—if you’re brave enough.
What's Included
Meeting and pickup
Arrive 15 MINUTES before the start time of your tour. Meet inside of the retail store, Portland Beer Hub (320 Fore Street, Portland, ME 04101), in downtown Portland's Old Port.
Itinerary
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1Old Port
Beneath the charm of Portland’s Old Port lies a darker story—one paved with cobblestones, secrets, and shadowy deals. This waterfront district once pulsed with illicit trade, backroom bribes, and speakeasies hidden in plain sight. As you stand among 19th-century brick facades and narrow alleys, it’s easy to imagine the bootleggers slipping through the night and the gangsters who ruled with intimidation. This stop peels back the polished surface to reveal the Old Port’s criminal underbelly—gritty, dangerous, and all too real.
2 hours • Admission ticket free
Additional info
- Service animals allowed
- Public transportation options are available nearby
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
- This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
- This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Rating
You can cancel up to 24 hours in advance of the experience for a full refund.
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