Portland Explorer: Mobsters and Lobsters True Crime in Old Port in Portland
Portland, United States

Portland Explorer: Mobsters and Lobsters True Crime in Old Port

Outty Ranking 60 4.8 · 5 traveler reviews1.5 hoursFrom $56

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September 2026

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Adults

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Age 12 and under

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From, per person$56
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Outty Ranking

60/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

4.8/5

Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Portland Explorer: Mobsters and Lobsters True Crime in Old Port worth booking?

Portland Explorer: Mobsters and Lobsters True Crime in Old Port is a 1.5-hour experience in Portland, United States, from $56 per person. It scores 60 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 4.8/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
60 / 100
Rating
4.8/5 (5)
Duration
1.5 hours
From
$56 per person

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 b

What you get

    About this experience

    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

    Included

    • Water at Portland Beer Hub
    • Guided walking tour with true crime stories
    • Engaging tales of True Crime in Portland Maine
    • Alcoholic beverages
    • Local Guide

    Not included

    • Gratuities for the guide
    • Food

    What you'll see and do

    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.

      90 minutes here

    Where it starts and ends

    Meeting point

    Portland

    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.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    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.

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Mon, Tue, Fri, Sat, Sun
    Group size
    Up to 12 travelers per booking
    Operated by
    Portland Explorer Tourism

    Know before you go

    • 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

    Photos

    Portland Explorer: Mobsters and Lobsters True Crime in Old Port in Portland, photo 2Portland Explorer: Mobsters and Lobsters True Crime in Old Port in Portland, photo 3

    Good to know

    Duration
    1.5 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Tue, Fri, Sat, Sun
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    2
    Verdict
    Worth a Look

    Why this scores 60

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)80
    Review evidence (18% weight)25
    Booking momentum (14% weight)18
    Value for money (12% weight)69
    Listing quality (10% weight)80
    Local standing (8% weight)52
    Booking flexibility (8% weight)100

    Portland Explorer: Mobsters and Lobsters True Crime in Old Port: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Portland.

    How much does Portland Explorer: Mobsters and Lobsters True Crime in Old Port cost?

    +

    Prices start at $56 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Portland usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Portland Explorer: Mobsters and Lobsters True Crime in Old Port take?

    +

    Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Portland is not rushed.

    Is Portland Explorer: Mobsters and Lobsters True Crime in Old Port worth it?

    +

    It holds an Outty Ranking of 60 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.8/5 across 5 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Portland, and how flexible the cancellation terms are.

    Can I cancel or reschedule Portland Explorer: Mobsters and Lobsters True Crime in Old Port?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Portland Explorer: Mobsters and Lobsters True Crime in Old Port suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Portland Explorer: Mobsters and Lobsters True Crime in Old Port?

    +

    Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Portland can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Portland and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.

    Where does Portland Explorer: Mobsters and Lobsters True Crime in Old Port start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Portland within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Portland?

    +

    Portland sells lighthouse and lobster-boat tours in Casco Bay, Old Port food and brewery walks, seal and puffin cruises, and fall foliage runs up the Maine coast. On Outty we rank every Portland experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local, Portland, Maine: Hidden Histories Guided Walking Tour, A Walk Through Time Tour in Portland. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Portland?

    +

    June to October, with peak foliage in early October. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Portland?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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