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Portland Explorer: Mobsters and Lobsters True Crime in Old Port

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.

Portland Explorer: Mobsters and Lobsters True Crime in Old Port

1 hour 30 minutesFree Cancellation

2-Hour Portland Old Port Ghost Walking Tour

2-Hour Portland Old Port Ghost Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

Bug Light

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

3 hoursFree Cancellation

Old Port Culinary Walking Tour from Portland

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Old Port Culinary Walking Tour from Portland

2 to 3 hoursFree Cancellation

One of the scenic working waterfronts

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

3 hoursFree Cancellation

Likely to Sell Out

Portland, Maine: Hidden Histories Guided Walking Tour

With this small-group walking tour, you'll go beyond lobsters and lighthouses and get a look at the true Portland, Maine—across 400 years of history. Meander downtown and the Old Port, visiting hidden landmarks and learning about Wabanaki leaders and other people and events left out of the history books. Discover centuries of destruction, revival, underrepresented perspectives, and other elements that mainstream tours gloss over.

Portland, Maine: Hidden Histories Guided Walking Tour

2 hoursFree Cancellation

A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

2 hoursFree Cancellation

Likely to Sell Out

Portland, Maine: Black History Guided Walking Tour

Maine's Black community is small, but its history here goes back more than 400 years. On this guided tour, you’ll dive deep into Portland’s Black history, discovering how this community—national leaders, laborers, skilled workers, activists, and more—fought for freedom and equality and defined the state's path. From Frederick Douglass to lesser-known Black Yankees, there’s far more here than meets the eye, and with this tour, you’ll learn all about it.

Portland, Maine: Black History Guided Walking Tour

2 hoursFree Cancellation

Top Attractions in Portland

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The Portland Head Light standing on the rock during sunset.

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Portland Head Light

The Ram Island Ledge Light in Casco Bay on a cloudy day.

Attractions

Casco Bay

Fort Gorges rising up from the surface of Portland Harbor.

Attractions

Fort Gorges

Eastern Promenade

Attractions

Eastern Promenade

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