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Portland City Tours

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Choose from one of these 3 City Tours to Portland in 2025-2026 to explore the streets and take in the cityscapes of Portland on a trip seamlessly planned by the Portland experts at Adventure Life. Breathe in the culture, smell the local cuisine, and experience the people of Portland on one of these extraordinary small group or private tours. Your options will likely include walking tours, bus tours, and boat tours, all led by exceptional multi-lingual local tour guides. Select any the urban exploration tours below and customize it to fit your personal interests with the help of one of Adventure Life's expert Portland trip planners. 
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    • Portland
Visit Portsmouth
from $7,299
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New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
  • Explore Portland
  • Watch whales in Saguenay Fjords
  • Walk Old Quebec streets
  • Explore Charlottetown history
Starts / Ends
Portland / Toronto
Activity Level
Variable
Experience a 12-day cruise from Portland to Toronto aboard Victory I and enjoy coastal views, local cuisine, and relaxing days at sea. This immersive journey blends Canadian culture, maritime history, and scenic waterways for a unique small-ship cruising experience.
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Edgartown on Martha's Vineyard
from $10,170
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New England Explorer

Boston Roundtrip - 12 Day Itinerary aboard American Patriot
  • Visit Portland Head Lighthouse
  • Learn about Wabanaki culture
  • Tour Bath's Maritime Museum
  • Discover Martha’s Vineyard Museum
Starts / Ends
Boston / Boston
Activities
Urban Exploration, Archaeological Site Visits, Village Visits, Local Market Visits
Activity Level
Variable
Embark on a 12-day coastal cruise of New England aboard American Patriot. Visit Portland, Rockland, Bar Harbor, Boothbay Harbor, Bath, Gloucester, Newport, and Martha’s Vineyard. Enjoy guided tours, seafood feasts, museums, and scenic cruising.
Cruise Details
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Golden light over the Chicago skyline
from $5,999
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New England and Canada

Montreal to Portland - 10 Day Itinerary aboard Victory I
  • Explore Montreal's European charm
  • Visit Halifax’s Citadel Hill
  • Stroll Portland’s historic streets
  • Enjoy a scenic whale-watching
Starts / Ends
Montreal / Portland
Activities
Whale Watching
Activity Level
Variable
Set sail on a 10-day cruise from Montreal to Portland aboard the Voyager I. Experience Montreal’s European charm and explore Quebec City’s historic streets. Enjoy whale-watching in Saguenay Fjord and discover Charlottetown’s coastal beauty. Sail through the Strait of Canso, visit Halifax’s bustling waterfront, and end in vibrant Portland, Maine.
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