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Bootleggers, Bosses & Bloodshed

Bootleggers, Bosses & Bloodshed

By Portland Explorer Tourism
10 out of 10
Free cancellation available
Price is ￥7,305 per adult
See tickets
Features
  • Free cancellation available
  • 2h
  • Mobile voucher
  • Instant confirmation
Overview

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.

Activity location

  • Old Port
    • 04101, Portland, Maine, United States

Meeting/Redemption Point

  • Portland Beer Hub
    • 320 Fore Street
    • 04101, Portland, Maine, United States

Check availability

Bootleggers
  • Activity duration is 2 hours2h
    2h
  • English
Language options: English
Starting time: 6:30pm
Price details
￥7,305 x 1 Adult￥7,305
Total
Price is ￥7,305
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What's included, what's not

  • What's includedWhat's includedWater at Portland Beer Hub
  • What's includedWhat's includedEngaging tales of Portland’s mobster history
  • What's includedWhat's includedGuided walking tour with true crime stories
  • What's excludedWhat's excludedGratuities for the guide

Know before you book

  • 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

Activity itinerary

Old Port
  • 2h
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.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIESOld Port
    • 04101, Portland, Maine, United States

Meeting/Redemption Point

  • PEOPLEPEOPLEPortland Beer Hub
    • 320 Fore Street
    • 04101, Portland, Maine, United States

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