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Portland Trips with Village Visits

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Explore remote villages on one of the below 6 unique Portland cultural experiences for 2026 or 2027. Visit the local village, meet the people, experience local cuisine with a local English speaking guide on your own private tour or small group guided tour. Discover unique local cultures on trips that include activities like Wildlife Viewing, Archaeological Site Visits, Urban Exploration, Whale Watching, and Local Market Visits and cost from $5,240 for experiences of 9 to 29 days. Tell us about your ideal Portland cultural trip and our Portland experts will help you plan every detail of your next trip.

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Beautiful seascapes in Maine
from $5,240
Savings
EXPLORE

Maine Coast & Harbors Round-Trip Cruise

Portland Roundtrip - 9 Day Itinerary aboard American Independence
  • Explore Historic Portland
  • Discover Fort Knox
  • Explore Acadia National Park
  • Discover Maine Maritime Heritage
Starts / Ends
Portland / Portland
Activities
Wildlife Viewing, Village Visits, Archaeological Site Visits, Urban Exploration
Activity Level
Variable
Explore Maine’s coast on a 9-day cruise from Portland aboard American Independence. Visit Bucksport, Bangor, Bar Harbor, Rockland, Camden, Boothbay Harbor, and Bath. Discover Fort Knox, Acadia National Park, maritime heritage, seafood traditions, and coastal communities across southern and midcoast Maine.
Cruise Details
0
from $25,010
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Fall Foliage on the St. Lawrence with Smithsonian Journeys

Toronto - Boston - 13 Day Itinerary aboard Le Bellot
  • Sail the scenic St. Lawrence Seaway
  • Stroll Old Montreal streets
  • Explore Prince Edward Island
  • Experience the Acadian culture
  • Explore Nova Scotia and Lunenburg
Starts / Ends
Toronto / Boston
Activities
Wine Tasting
Activity Level
Variable
Sail Canada’s St. Lawrence Seaway on a 13-day cruise aboard Le Bellot. Visit Toronto, Montreal, Quebec, Tadoussac, Charlottetown, Magdalen Islands, Sydney, Lunenburg, Portland, and Boston. Enjoy whale watching, historic tours, cultural experiences, scenic landscapes, and regional cuisine throughout this journey.
Cruise Details
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Colorful sunrise at Portland Head Lighthouse in Maine
from $9,899
Save $6000
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East Coast: Jacksonville to Halifax

Jacksonville to Halifax - 16 Day Itinerary aboard Victory I
  • Explore Jacksonville's waterfront
  • Discover Brunswick’s Golden Isles
  • Stroll Savannah’s historic squares
  • Discover Norfolk’s naval heritage
Starts / Ends
Jacksonville / Halifax
Activity Level
Variable
Sail from Jacksonville to Halifax aboard Victory I, visiting historic coastal ports in Georgia, South Carolina, North Carolina, Virginia, Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Nova Scotia. Explore waterfronts, museums, historic sites, mansions, naval landmarks, and lighthouses along the Atlantic coast.
Cruise Details
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Portsmouth, New Hampshire
from $9,899
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East Coast: Halifax to Jacksonville

Halifax to Jacksonville - 16 Day Itinerary aboard Victory I
  • See Portland Head Light
  • Discover Provincetown galleries
  • Tour Newport's grand mansions
  • See Charleston's historic landmarks
Starts / Ends
Halifax / Jacksonville
Activity Level
Variable
Embark on a 16-day East Coast cruise aboard Victory I. Explore Halifax and Peggy’s Cove before visiting Portland, Portsmouth, Provincetown, Newport, and New London. Continue south to Norfolk, Wilmington, Charleston, Savannah, Brunswick, and Jacksonville. Experience New England’s coastal heritage, Southern history, and Atlantic scenery.
Cruise Details
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Charming Quebec City
from $6,799
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Quebec City To Portland

Quebec City - Portland - 12 Day Itinerary aboard Victory II
  • Sail the Saguenay Fjord
  • Explore Gaspe’s Forillon Park
  • Visit Peggy’s Cove Lighthouse
  • Visit Charlottetown’s streets
Starts / Ends
Quebec City / Portland
Activity Level
Variable
Cruise from Quebec City to Portland on a 12-day cruise aboard Victory II, visiting Saguenay, Baie-Comeau, Gaspe, Charlottetown, and Halifax. Explore historic cities, coastal landscapes, the Saguenay Fjord, and maritime landmarks. Experience French Canadian heritage, Atlantic scenery, and historic ports across Canada and New England.
Cruise Details
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Visit Portsmouth
from $18,198
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5 Great Lakes + St. Lawrence Seaway: Montreal to Jacksonville

Montreal to Jacksonville - 29 Day Itinerary aboard Victory I
  • Watch Saguenay Fjord belugas
  • Kayak Gaspe's Forillon coastline
  • Tour Halifax's hilltop Citadel
  • Admire Newport's Cliff Walk
Starts / Ends
Montreal / Jacksonville
Activities
Whale Watching, Local Market Visits, Kayaking
Activity Level
Variable
Embark on a 29-day voyage aboard Victory I, from Montreal to Jacksonville, linking the St. Lawrence Seaway with the Atlantic Seaboard. Walk Old Quebec, watch beluga whales in the Saguenay Fjord, and explore Halifax and Newport before reaching Florida.
Cruise Details
0
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Kassandra Magruder Adventure Life employee profile
Kassandra M.
East Coast of US

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