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Bootleggers, Bosses & Bloodshed
Portland, Maine, USA
$50.00
This is an experience gift voucher. The recipient will book the experience after
they redeem the gift voucher.
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.
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Bootleggers
Tour guide
Language: English
Human tour guide
Duration: 2 hours
Availability depends on seasonality and number of participants. Bookings can not be made for the same day. Please read our TnC’s.
When giving as a gift, your recipient can choose a date at their convenience during a booking process. Otherwise, you can choose one after checkout and voucher redemption.
When giving as a gift, your recipient can choose a date at their convenience during a booking process. Otherwise, you can choose one after checkout and voucher redemption.
Check available dates by emailing us at [email protected]
- Guided walking tour with true crime stories
- Engaging tales of Portland’s mobster history
- Water at Portland Beer Hub
- Gratuities for the guide
Meeting point
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.
Return details
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.
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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.
If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
If it’s canceled because the minimum isn’t met,
you’ll be offered a different date/experience or a full refund.
How it works?
01
—
You choose from 10,000+ experience gifts
02
—
We deliver the eVoucher or the Physical box to the recipient
03
—
Recipient books the experience and creates unforgettable memories!
Bootleggers, Bosses & Bloodshed
Portland, Maine, USA
$50.00
This is an experience gift voucher. The recipient will book the experience after
they redeem the gift voucher.
How it works?
01
—
You choose from 10,000+ experience gifts
02
—
We deliver the eVoucher or the Physical box to the recipient
03
—
Recipient books the experience and creates unforgettable memories!