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Select one of the below 11 best New England trips for 2025 and 2026. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Portland, Boston, Newport, Bath, and Martha's Vineyard. Our New England trips for 2025 feature Archaeological Site Visits, Urban Exploration, Village Visits, Local Market Visits, and Whale Watching, and start from $4,999 for trips of 8 to 16 days. Contact Adventure Life's New England trip planning experts to start planning your next seamless trip.
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    • New England
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
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
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
0
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
0
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
0
Enjoy scenic New England
from $7,790
Savings
EXPLORE

New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty
  • Enjoy Block Island's beaches
  • Explore Whaling Museum New Bedford
  • Discover Martha's Vineyard's towns
  • Learn whaling legacy and maritime
Starts / Ends
Nantucket / Newport
Activity Level
Variable
Embark on an 8-day cruise aboard American Liberty through New England, exploring maritime history from Providence to Newport. Indulge in lobster bakes, visit whaling museums, and wander charming cobblestone streets.
Cruise Details
0
Sailing in Boston
from $6,350
Savings
EXPLORE

Yankee Seaports

Boston - New York - 8 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 City
Activity Level
Variable
Join this 8-day Yankee Seaports 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
Aerial view of New York City at dusk
from $8,600
EXPLORE

Montreal to New York, NY

Montreal - New York - 12 Day Itinerary aboard Silver Shadow
  • Discover Montreal’s landscape
  • Explore Quebec City historic charm
  • Experience Saguenay’s wilderness
  • Stroll Charlottetown’s streets
Starts / Ends
Montreal / New York City
Activities
Urban Exploration, Wildlife Viewing, Whale Watching, Kayaking
Activity Level
Variable
Embark on a 12-day cruise from Montreal to New York on the Silver Shadow, exploring Canada's Atlantic coast and New England's charm. Highlights include Quebec City, Prince Edward Island, and excursions like hikes and heritage walks, offering a blend of culture and relaxation.
Cruise Details
0
Explore beautiful Montreal
from $7,299
EXPLORE

New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
  • Explore Portland
  • Explore Charlottetown
  • Sail on the Gulf of St. Lawrence
  • Enjoy whale watching near Tadoussac
Starts / Ends
Portland / Toronto
Activity Level
Variable
Experience a 12-day cruise from Portland to Toronto aboard Victory I and explore historic cities, stunning landscapes, and vibrant cultures. From whale-watching in Tadoussac to exploring Quebec City's old town, this cruise offers a unique blend of adventure and relaxation.
Cruise Details
0
Explore beautiful and historic Montreal
from $17,100
EXPLORE

Fall Foliage on the St. Lawrence: Québec to the Canadian Maritimes – with Smithsonian Journeys

Toronto - Boston - 15 Day Itinerary aboard Le Champlain
  • Sail the scenic St. Lawrence Seaway
  • Visit Montreal, a cosmopolitan city
  • Visit Old Quebec, a UNESCO site
  • Colonial seaport of Charlottetown
Starts / Ends
Toronto / Boston
Activities
Village Visits
Activity Level
Variable
On this 15-day Fall Foliage cruise from Toronto to Boston aboard Le Champlain, explore the stunning coastlines of eastern Canada and northern New England. Sail the St. Lawrence Seaway, visiting cities like Montréal, Québec City, and Charlottetown. Discover Nova Scotia's history in Baddeck, Louisbourg, and Lunenburg before concluding in Boston.
Cruise Details
0
Golden light over the Chicago skyline
from $4,999
EXPLORE

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
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.
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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