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Top Portland Tours & Cruises in 2025

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Discover the best the world has to offer with Adventure Life’s expert-curated Portland tours 2025. From to hidden gems off the beaten path, our 7 top-rated itineraries take you deep into Portland’s breathtaking landscapes. Guided by bilingual experts, these immersive experiences cater to adventurers seeking unique journeys in small groups or customizable private tours.

Choose from a variety of 9 to 16 days itineraries starting at $5,999 to $24,875. You’ll find options that suit your travel style. Whether you’re passionate about Archaeological Site Visits, Urban Exploration, Village Visits, Local Market Visits, and Whale Watching or eager to explore Portland’s rich culture and natural beauty, our Portland tours 2025 deliver unforgettable moments. Each itinerary blends awe-inspiring exploration with a commitment to sustainability to ensure your adventure supports the preservation of our planet.

Adventure Life’s dedication to personalized travel promises your Portland tour 2025 is seamless from start to finish. From arranging transportation to selecting accommodations tailored to your preferences, we’ll take care of every detail. Our expert recommendations and insider tips make your journey even more enriching.

Contact our specialists today to start planning your Portland tour 2025. Whether you’re a solo traveler, a couple, or part of a group, Adventure Life will create a transformative experience you’ll treasure forever.
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    • Portland
Beautiful seascapes in Maine
from $6,710
Savings
EXPLORE

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
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.
Cruise Details
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Explore beautiful Montreal
from $7,299
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.
Cruise Details
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Eastern Point Lighthouse, Gloucester, Massachusetts
from $11,030
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Independence
  • View Cape Elizabeth lighthouses
  • Discover Nantucket whaling history
  • Walk Portland’s Old Port
  • Visit Maine Maritime Museum
Starts / Ends
Portland / New York
Activities
Wine Tasting
Activity Level
Variable
Cruise the New England coast on a 16-day cruise from Portland to New York aboard American Independence. This journey delivers history, culture, and natural beauty through iconic destinations, guided tours, and onboard enrichment—all while experiencing the region’s fall colors and crisp sea air.
Cruise Details
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Visit Portsmouth
from $13,285
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Glory
  • Walk Portland’s working waterfront
  • Tour Newport’s seaside mansions
  • Walk at cobblestone streets
  • Visit Gloucester’s Maritime Museum
Starts / Ends
Portland / New York
Activity Level
Variable
Sail the coast of New England on a 16-day New England Fall Foliage cruise aboard American Glory, visiting historic cities and scenic harbors from Maine to New York. This cruise blends history, coastal charm, and iconic landmarks with smooth sailing and guided excursions.
Cruise Details
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Visit Plymouth
from $13,940
Savings
EXPLORE

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
Wildlife Viewing, 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
0
Golden light over the Chicago skyline
from $5,999
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
Urban Exploration, Archaeological Site Visits, 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.
Cruise Details
0
Explore the parks around Quebec City for a view of the city
from $7,399
EXPLORE

New England and Canada

Toronto to Portland - 13 Day Itinerary aboard Victory II
  • Explore Toronto's landmarks
  • Visit Quebec City's historic sites
  • Go on a whale-watching adventure
  • Visit Halifax’s historic waterfront
Starts / Ends
Toronto / Portland
Activity Level
Variable
Embark on a 12-day cruise from Toronto to Portland aboard Victory II, experiencing vibrant cities, breathtaking landscapes, and rich maritime heritage. This adventure offers a blend of urban exploration, natural beauty, and cultural immersion.
Cruise Details
0
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