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New England Urban Exploration Cruises

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Explore the charming cityscapes and vibrant culture of New England on our 15 exceptional urban exploration tours for 2026. Surrounded by rich history, breathtaking landscapes, and quaint coastal towns, our New England city tours provide a deep dive into the heart of this remarkable region. Over 9 to 29 days, you will discover the allure of New England, from the stunning beauty of Lake Michigan to the thundering Niagara Falls and the historic maritime city of Montreal. Delight in renowned lobster dishes, explore picturesque towns, and appreciate the arts and local artists along the eastern seaboard. To embark on a journey that uncovers the magic of New England's urban environments and hidden gems, contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • New England
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
Urban Exploration, Village Visits, Archaeological Site Visits, Wildlife Viewing
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
Edgartown on Martha's Vineyard
from $7,180
EXPLORE

Charm and heritage of the North American shores

Halifax to New York - 9 Day Itinerary aboard L'Austral
  • See Lunenburg UNESCO historic town
  • Eastport Maritime Historic Site
  • See Newport Gilded Age mansions
  • Martha's Vineyard island escape
Starts / Ends
Halifax / New York
Activity Level
Variable
Explore Canada and New England on a 9-day cruise aboard L'Austral. Visit Halifax, Lunenburg, Yarmouth, Eastport, Portland, Boston, Oak Bluffs, Newport, and New York. Discover maritime history, UNESCO heritage sites, coastal landscapes, iconic landmarks, and charming seaside towns throughout the voyage.
Cruise Details
0
Admire the charming houses of Martha's Vineyard
from $6,350
Savings
EXPLORE

New England Islands Cruise

Providence Roundtrip - 9 Day Itinerary aboard American Glory
  • Explore Historic Providence Today
  • Explore Martha’s Vineyard Today
  • Explore Nantucket Whaling History
  • Visit Newport’s Historic Landmarks
Starts / Ends
Martha's Vineyard / Newport
Activity Level
Variable
Explore Providence, Martha’s Vineyard, Nantucket, Block Island, Newport and Bristol on a 9-day cruise aboard American Glory, from Providence to Providence. Discover maritime history, historic towns, museums, coastal landscapes and local traditions across Rhode Island and Massachusetts, with time to explore destinations and coastal heritage today.
Cruise Details
0
Sailing in Boston
from $6,350
Savings
EXPLORE

Northeast Harbors Cruise

Boston - New York - 9 Day Itinerary aboard American Glory
  • Visit the Massachusetts Maritime
  • Explore the Mystic Seaport Museum
  • Travel to Old Saybrook
  • Stroll around Sag Harbor
Starts / Ends
Boston / New York
Activity Level
Variable
Join this 9-day Northeast Harbors cruise from Boston to New York aboard American Glory. Explore historic Boston before visiting picturesque Plymouth, MA, and the grandeur of Newport. Dive into maritime history in New London, Mystic, and Essex, CT. Lastly, enjoy an evening cruise around New York Harbor.
Cruise Details
0
Explore beautiful Montreal
from $10,895
EXPLORE

Autumn Foliage of Canada & America's East Coast

Montreal - New York - 12 Day Itinerary aboard Scenic Eclipse
  • Explore Montreal Old Town
  • Tour Pictou to explore museums
  • View Oak Bluffs gingerbread cottage
  • Admire New York City skyline
Starts / Ends
Montreal / New York City
Activity Level
Variable
Join a 12-day cruise on the Scenic Eclipse along Canada's eastern coast and New England, exploring historic Quebec City and Halifax's rich Scottish and Acadian heritage. Enjoy stops in Oak Bluffs' colorful gingerbread houses and the Cape Cod Canal, finishing with an overnight stay in New York City.
Cruise Details
0
Aerial view of New York City at dusk
from $6,350
Savings
EXPLORE

Northeast Harbors Cruise

New York - Boston - 9 Day Itinerary aboard American Glory
  • Explore New York landmarks
  • Explore Sag Harbor history
  • Explore Newport historic districts
  • Discover Plymouth colonial history
Starts / Ends
New York / Boston
Activities
Wine Tasting
Activity Level
Variable
Experience a 9-day cruise from New York to Boston aboard American Glory, with time to explore New York, Sag Harbor, Old Saybrook, Essex, New London, Mystic, Newport, Plymouth, and Boston. Discover maritime museums, historic districts, coastal landmarks, local communities, and sites connected to American history along the New England coast.
Cruise Details
0
Colorful sunrise at Portland Head Lighthouse in Maine
from $9,899
Save $6000
EXPLORE

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
0
Portsmouth, New Hampshire
from $9,899
EXPLORE

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
0
Visit Portsmouth
from $7,299
Save $6000
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
0
Visit Portsmouth
from $18,198
EXPLORE

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
Local Market Visits, Whale Watching, 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
Stroll by the river running through Quebec City
from $7,299
EXPLORE

Five Great Lakes + St. Lawrence Seaway: Portland to Toronto

Portland to Toronto - 13 Day Itinerary aboard Victory II
  • Cruise Atlantic Canada to Toronto
  • Wander UNESCO Old Quebec
  • Discover Charlottetown's history
  • Sail the Saguenay Fjord
  • Tour Old Montreal's basilica
Starts / Ends
Portland / Toronto
Activity Level
Variable
Embark on a 13-day cruise Victory II and sail from Portland, Maine to Toronto, Ontario, calling at Nova Scotia, Prince Edward Island, Quebec City, and Montreal. This voyage links rugged Atlantic shores, deep glacial fjords, and Great Lakes channels into one seamless passage across North American coastal waterways.
Cruise Details
0
Aerial View of Halifax Skyline
from $5,999
SailFree
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
0
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