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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 5 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 9 to 15 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
Beautiful seascapes in Maine
from $6,710
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Maine Coast & Harbors Cruise

Portland - Bangor - 9 Day Itinerary aboard American Glory
  • Cruise through Casco Bay
  • Sample fresh oysters in Bath
  • Visit Boothbay Harbor's garden
  • Taste a traditional lobsterbake
Starts / Ends
Portland / Bar Harbor
Activities
Wildlife Viewing
Activity Level
Variable
Cruise Maine’s coast for 9 days aboard American Glory. Sail Casco Bay, visit a Bath oyster farm, explore Boothbay’s gardens, enjoy a Rockland lobsterbake, tour Acadia National Park in Bar Harbor, and walk its quaint downtown. In Castine, learn its Revolutionary War history, and finish in Bangor, Stephen King’s hometown and inspiration for Derry.
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Visit Plymouth
from $13,940
Savings
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Grand New England Cruise

Roundtrip Boston - 15 Day Itinerary aboard American Patriot
  • Explore Portland iconic lighthouses
  • Discover Bath historic shipyards
  • Explore Bangor Victorian mansions
  • Discover Portsmouth architecture
Starts / Ends
Boston / Boston
Activities
Village Visits, Local Market Visits
Activity Level
Variable
Set sail on a 15-day cruise aboard American Patriot. Discover historic seaports and savor New England's charm with a Maine lobster bake.
Cruise Details
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Visit Portsmouth
from $13,155
Savings
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New England Fall Foliage Cruise

Portland - New York - 15 Day Itinerary aboard American Glory
  • Visit Portsmouth and Gloucester
  • Explore Martha’s Vineyard & Newport
  • Explore Sag Harbor
  • Discover Mystic Seaport
Starts / Ends
Portland / New York City
Activity Level
Variable
On this 15-day New England Fall Foliage Cruise from Portland to New York aboard American Glory, explore New England's waterways adorned with fall foliage, and natural landscapes. Visit towns, villages, and estates, all curated with experiences. Conclude with a cruise around the Statue of Liberty against the New York City skyline.
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Golden light over the Chicago skyline
from $4,999
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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
Archaeological Site Visits, Urban Exploration, 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 conclude in vibrant Portland, Maine, where arts and seafood await.
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Eastern Point Lighthouse, Gloucester, Massachusetts
from $10,835
Savings
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New England Fall Foliage Cruise

Portland - New York - 15 Day Itinerary aboard American Independence
  • Visit Portsmouth and Gloucester
  • Explore Martha’s Vineyard & Newport
  • Explore Sag Harbor
  • Discover Mystic Seaport
Starts / Ends
Portland / New York City
Activities
Adventure Options, Land & Sea Exploration
Activity Level
Variable
On this 15-day New England Fall Foliage Cruise from Portland to New York aboard American Independence, explore New England's waterways adorned with fall foliage, and natural landscapes. Visit towns, villages, and estates, all curated with experiences. Conclude with a cruise around the Statue of Liberty against the New York City skyline.
Cruise Details
0
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