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Tranquil moment in a harbor in Maine

Maine Urban Exploration Tours

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Discover the historic charm of Maine's urban landscapes on Adventure Life's 3 city tours in Portland for 2025. Wander through the picturesque streets of Portland and explore coastal towns while immersing yourself in the local art scene. Delve into the region's rich history and appreciate the work of local artists as you embark on a journey from Portland to Saint John over 10 to 12 days. This urban exploration tour offers a relaxed pace, perfect for soaking in the beauty of the Eastern seaboard and enjoying renowned lobster dishes along the way. To experience the best of Maine's coastal gems and vibrant urban culture, contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Maine
Edgartown on Martha's Vineyard
from $10,170
Savings
EXPLORE

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.
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Visit Portsmouth
from $7,299
Save $5000
EXPLORE

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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Golden light over the Chicago skyline
from $5,999
Save $5000
EXPLORE

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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