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Our Portland Trips & Vacation Packages

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Discover the vibrant city of Portland, Maine, with our 5 diverse tours for 2026. Join us on one of these top-rated trips and vacation packages to explore this charming coastal destination. From indulging in the local food scene to exploring the picturesque lighthouses along the rugged coastline, there is something for every traveler in Portland. Immerse yourself in the rich maritime history, enjoy whale watching excursions, and stroll through the cobblestone streets lined with boutique shops and art galleries. Whether you're interested in cultural experiences, food & wine tours, or outdoor adventures like hiking or kayaking, Portland offers a perfect blend of activities. With tours ranging from short day trips to longer adventures, there is an option for every schedule. Don't miss the chance to experience the beauty and charm of Portland, Maine, with Adventure Life. Contact one of our tour specialists for help planning your next seamless trip.
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    • Portland
Visit Portsmouth
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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Aerial View of Halifax Skyline
from $5,999
EXPLORE

New England and Canada

Montreal to Portland - 10 Day Itinerary aboard Victory I
  • Sail the Saguenay Fjords
  • Explore Canada history sites
  • Halifax waterfront walk
  • Atlantic Ocean crossing
Starts / Ends
Montreal / Portland
Activity Level
Variable
Set sail on a 10-day cruise from Montreal to Portland aboard Victory 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
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Charming Quebec City
from $6,799
EXPLORE

Quebec City To Portland

Quebec City - Portland - 12 Day Itinerary aboard Victory II
  • Explore Quebec City Old Port
  • See Baie-Comeau coastal landscapes
  • Portsmouth harbor historic town
  • Strait of Canso sailing
Starts / Ends
Quebec City / Portland
Activities
Whale Watching, Urban Exploration, Wildlife Viewing, Village Visits
Activity Level
Variable
Travel on a 12-day cruise from Quebec City to Portland aboard Victory II. Start in Quebec City and sail the St. Lawrence River to Saguenay, Baie-Comeau, Gaspe, Charlottetown, Halifax, and Portsmouth before ending in Portland. Explore fjords, coastal villages, historic ports, and Atlantic waters rich with maritime heritage.
Cruise Details
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Aerial View of Halifax Skyline
from $8,299
EXPLORE

New England and Canada

Montreal to Portland - 13 Day Itinerary aboard Victory I
  • Visit UNESCO-listed Old Quebec City
  • Charlottetown historic charm
  • Learn Yarmouth’s Acadian heritage
  • Sail through Saguenay Fjord
Starts / Ends
Montreal / Portland
Activity Level
Variable
Begin the 13-day voyage in Montreal with a hotel stay, then board Victory I and cruise through Quebec City, Saguenay Fjord, Charlottetown, Halifax, and Yarmouth before ending in Portland, Maine. Sail the Gulf of St. Lawrence and Strait of Canso while exploring historic towns, coastal villages, and maritime landmarks across Atlantic Canada.
Cruise Details
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Colorful sunrise at Portland Head Lighthouse in Maine
from $8,299
EXPLORE

New England and Canada

Montreal to Portland - 13 Day Itinerary aboard Victory II
  • Walk Quebec City's Old Town streets
  • Saguenay Fjord sailing
  • Gulf crossing experience
  • Tour Halifax historic citadel
Starts / Ends
Montreal / Portland
Activities
Archaeological Site Visits
Activity Level
Variable
Begin your 13-day voyage in Montreal with a hotel stay, then board Victory II and sail the St. Lawrence River to Quebec City, Saguenay, Baie-Comeau, and Gaspe. Cross the Gulf of St. Lawrence to Charlottetown, continue to Halifax and Yarmouth, and finish in Portland, Maine. Explore fortified cities, fjords, island capitals, and working waterfronts.
Cruise Details
0
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