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Zakim Bridge reflection on the Charles River in Boston

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Explore these 8 top Boston cruises for 2025 and 2026. Some of the most popular activities on our Boston trips include Urban Exploration, Village Visits, Archaeological Site Visits, Local Market Visits, and Wildlife Viewing. Discover with your expert local English-speaking guides who will show you the hot spots and the off-the-beaten-path hidden gems. We work with only the best small ships that carry under 500 fortunate guests, and we can give you unbiased advice to match you with the perfect ship and perfect cruise for your next vacation. Our Boston cruises start from $6,350 for cruises of 8 to 16 days. Contact one of Adventure Life's Boston cruise specialists for help planning a seamless trip.
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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
  • Join the St. Lawrence River Cruise
  • Visit Montréal’s Old Town
  • Visit Old Quebec, Saguenay Fjord
  • Experience Charlottetown
Starts / Ends
Toronto / Boston
Activity Level
Variable
Cruise the St. Lawrence River in 2025 on a scenic small ship journey from Toronto to Boston. Explore Montréal, Québec City, and the Saguenay Fjord on a classic St. Lawrence Seaway cruise, similar to Viking river cruise routes. Discover Acadian culture in Charlottetown and Cap-aux-Meules.
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
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
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
Explore beautiful and historic Montreal
from $12,890
EXPLORE

From Quebec to the Big Apple: Nature & Remarkable Cities

Montreal - New York - 14 Day Itinerary aboard Le Boreal
  • Quebec City walking tour
  • Wander Martha’s Vineyard
  • Visit Peggy’s Cove lighthouse
  • Spot whales in Saguenay Fjord
Starts / Ends
Montreal / New York City
Activities
Urban Exploration, Archaeological Site Visits, Village Visits, Local Market Visits
Activity Level
Variable
Sail from Montreal to New York on a 14-day cruise aboard Le Boreal. Explore Quebec, Halifax, Boston, and Martha’s Vineyard. Enjoy whale watching, historical tours, and gourmet tastings.
Cruise Details
0
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
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
from $12,670
EXPLORE

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

Toronto - Boston - 13 Day Itinerary aboard Le Bellot
  • Sail the scenic St. Lawrence Seaway
  • Visit Montreal, a cosmopolitan city
  • Explore Prince Edward Island
  • Experience the Acadian culture
  • Explore Nova Scotia and Lunenburg
Starts / Ends
Toronto / Boston
Activities
Wildlife Viewing
Activity Level
Variable
Explore eastern Canada and New England on a 13-day Smithsonian Journeys cruise. Sail from Toronto to Boston with stops in Quebec, PEI, Nova Scotia, and Cape Cod. Highlights include Montreal, Tadoussac, Magdalen Islands, Charlottetown, and Lunenburg. Includes expert talks and a shore excursion in each port.
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
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
Activities
Wine Tasting
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
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