• Old Port - Beneath the allure of Portland’s Old Port lies a more sinister tale—one marked by cobblestones, secrets, and clandestine dealings. This waterfront area was once alive with illegal trade, covert bribes, and speakeasies hidden in plain sight. As visitors stand among the 19th-century brick buildings and narrow alleys, it’s easy to envision the bootleggers moving stealthily through the night and the gangsters who ruled through fear. This stop uncovers the polished exterior to reveal the Old Port’s criminal underworld—gritty, perilous, and all too real.

• Water at Portland Beer Hub
• Engaging tales of Portland’s mobster history
• Guided walking tour with true crime stories

• Gratuities for the guide

Embark on a captivating journey into Portland’s intriguing history with this true crime tour, where hidden secrets lie behind historic facades and cobblestone streets echo with tales of corruption, violence, and vice. Discover the stories of ruthless mobsters, cunning bootleggers, ambitious bosses, and shocking scandals as this tour reveals the darker side of Maine’s largest city. Stroll along the very streets where speakeasies flourished, clandestine deals were struck under the cover of night, and power struggles led to bloodshed. Guided by knowledgeable experts, this exploration of Portland’s underworld promises unforgettable, spine-chilling stories. Are you ready to delve into the city’s past? Book now—if you dare.

For a full refund, cancel at least 24 hours before the scheduled departure time.