Top Maine Architecture Tours

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Uncover the Old Port's deeper past—where sailors, merchants, immigrants, and reformers all left their mark.

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom Trail, which honors the city’s fight for freedom and civil rights. The tour showcases the Old Port’s architectural charm and its transformation from a bustling shipping hub to a cultural center. Experience the tales of resilience embedded in its streets, from the Great Fire of 1866 to the revitalization efforts of the 1970s. Join fellow history enthusiasts for a memorable journey through Portland’s past and present. — Explore the historic Old Port district, a cultural and commercial hub — Walk along the Portland Freedom Trail, learning about civil rights — Discover stories of resilience, fire, and maritime life — Ideal for history lovers and those curious about Portland's heritage

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Self-Guided Audio Tour of Portland’s Historic Old Port District

2 hours to 2 hours 30 minutesFree Cancellation

from $10

Likely to Sell Out

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.

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4.8

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Old Port Culinary Walking Tour from Portland

2 to 3 hoursFree Cancellation

from $160

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.

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5.0

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Private Portland to Cape Ann, MA Castles & Coast

8 to 10 hoursFree Cancellation

from $325

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Top Maine Architecture Tours

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Top Attractions in Maine

Casco Bay

Fort Gorges

Eastern Promenade

Cape Neddick Nubble Lighthouse

Acadia National Park

Portland Head Light

Casco Bay

Fort Gorges

Eastern Promenade

Cape Neddick Nubble Lighthouse

Acadia National Park

Portland Head Light

Casco Bay

Fort Gorges

Eastern Promenade

Cape Neddick Nubble Lighthouse