Is this tour suitable for children?

Yes, children with an interest in history and comfortable walking shoes will enjoy the storytelling and exploration.

Dress comfortably for walking, and bring layers or rain gear depending on the season.

Are there any age restrictions?

The tour is recommended for ages 10 and up due to walking and historical content.

Can I bring food or drinks?

Yes, but please respect local properties and avoid eating during the tour.

How many people typically join?

Group sizes vary, but most tours host between 10-20 participants for an engaging experience.

Is parking available?

There are nearby parking options, but public transportation or walking is encouraged in downtown Portland.

Bootleggers, Bosses & Bloodshed | Walking Tour in Portland, Maine | Walking Tour | History Tour

Adventure Brief

Step back into Portland’s Prohibition era with an inspiring walking tour that uncovers hidden stories of bootlegging, gangsters, and secret speakeasies. Perfect for history lovers and adventurers alike, this experience offers a thrilling journey through the city’s past.

2–2.5 hours

moderate

From $57.67

Discover Portland, Maine, in a whole new way with 'Bootleggers, Bosses & Bloodshed,' a captivating walking tour that brings history and local storytelling to life. Perfect for history buffs and adventure seekers alike, this experience takes you through the city's past during Prohibition, exploring notorious bootlegging routes, shadowy speakeasies, and legendary figures who shaped the era. As you walk through historic neighborhoods and hidden alleys, knowledgeable guides share engaging stories filled with intrigue, crime, and community spirit, making it more than just a tour—it's an immersive journey back in time. What sets this adventure apart is its combination of rich storytelling, off-the-beaten-path locations, and the chance to step into a pivotal chapter of Portland’s history. Whether you're a local wanting a deeper appreciation of your city or a visitor eager for authentic experiences, this tour offers a memorable glimpse into Maine’s clandestine past and vibrant culture. Comfortable walking shoes and curiosity are all you need to enjoy this exploration that connects the past with the present, leaving you with stories to share and a new perspective on Portland’s historic streets.

About Portland Explorer LLC

Portland Explorer LLC is a Portland, Maine–based tour operator offering a curated selection of guided experiences that highlight the city’s maritime history, culinary scene, and coastal scenery.

From guided walking tours through the Old Port and architectural stops like Victoria Mansion and Custom House to relaxing sunset and scenic harbor cruises through Casco Bay, the company focuses on showcasing Portland’s landmarks and waterfront views.

Several experiences depart from Portland Beer Hub, including specialty offerings that pair local beverages with sightseeing. Those options include craft beer and cider tastings, a three-stop Local Pour Tour, wine-focused walking experiences, and elevated outings such as Pearls and Prosecco featuring oysters and prosecco on the water.

Adventure-minded guests can combine active fun with tastings on tours like Axes and Ales or Lighthouse to Lagers.

For history enthusiasts, Portland Explorer operates lighthouse tours and a Fort Tour to Fort Scammel on House Island, providing access to historic coastal defense sites and interpretation about maritime heritage.

Tours range from walking routes to boat-based cruises, appealing to a wide range of interests and mobility levels.

Tour descriptions emphasize authentic local stories, landmark viewpoints, and curated beverage or food pairings. Portland Explorer serves visitors and residents seeking guided, small-group experiences that explore Portland’s coastline, lighthouses, breweries, and historic districts. Booking details, meeting locations, and specific itinerary notes are provided for each tour to help guests choose the right experience.

Customer questions about accessibility, duration, and group size are answered with clear pre-booking information and logistical details for every tour.