Bootleggers, Bosses & Bloodshed
Things to know
About the Activity
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.2 hours
Instant Confirmation
Mobile ticket
Availability and Prices
Free cancellation up to 24 hours before the experience starts (local time)
Travel Date
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Travelers
Inclusions & Exclusions
Water at Portland Beer Hub
Engaging tales of Portland’s mobster history
Guided walking tour with true crime stories
Gratuities for the guide
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Travel Itinerary
- Maximum 15 travellers in this tour.
Locations in the itinerary
1
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 FreeView Location
Meeting and Pickup
Starting point
1
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. View Location
End point
1
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. View Location
Pickup details
Customers must make their own way to and meet at the start point- Travelers CANNOT choose a custom pickup or meeting location.
Additional Information
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Language And Guide
Tour Guide Available In
- English
Ticket Details
- Mobile or paper ticket accepted
- One per booking
Ticket Redemption
No redemption point. This is a direct entry ticketCancellation & Refunds
Cancellable up to 24 hours before the travel date (local supplier time) for a full refund. A 100% cancellation penalty applies for cancellations submitted less than 24 hours before the start time.- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Suplier may cancel the activity on account of bad weather conditions.
- Suplier may cancel the activity due to too few participants.
- Cancel at least 1 day before activity starts in America/New_York time to receive 100% refund.
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No reviews found!Operated by Portland Explorer TourismCreated on 12 Oct 2019Created on 30 Apr 2025
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