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Zakim Bridge reflection on the Charles River in Boston

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Select one of the below 4 best Boston trips for 2025 and 2026. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring . Our Boston trips for 2025 feature Urban Exploration, Archaeological Site Visits, Local Market Visits, Village Visits, and Wildlife Viewing, and start from $5,750 for trips of 8 to 13 days. Contact Adventure Life's Boston trip planning experts to start planning your next seamless trip.
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Explore historic Boston
from $6,350
Savings
EXPLORE

Cape Codder Cruise

Boston, MA Roundtrip - 9 Day Itinerary aboard American Glory
  • Walk Boston’s Freedom Trail
  • Tour Newport’s grand mansions
  • Enjoy Martha’s Vineyard Museum
  • See massive whale skeletons
Starts / Ends
Boston / Boston
Activity Level
Variable
Embark on an 9-day Cape Cod cruise aboard American Glory, round-trip from Boston. Visit Provincetown, Plymouth, Martha’s Vineyard, Newport, and New Bedford. Step into colonial history, maritime culture, and coastal scenery.
Cruise Details
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Edgartown on Martha's Vineyard
from $10,170
Savings
EXPLORE

New England Explorer

Boston Roundtrip - 12 Day Itinerary aboard American Patriot
  • Visit Portland Head Lighthouse
  • Learn about Wabanaki culture
  • Tour Bath's Maritime Museum
  • Discover Martha’s Vineyard Museum
Starts / Ends
Boston / Boston
Activities
Urban Exploration, Local Market Visits, Archaeological Site Visits, Village Visits
Activity Level
Variable
Embark on a 12-day coastal cruise of New England aboard American Patriot. Visit Portland, Rockland, Bar Harbor, Boothbay Harbor, Bath, Gloucester, Newport, and Martha’s Vineyard. Enjoy guided tours, seafood feasts, museums, and scenic cruising.
Cruise Details
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Sailing in Boston
from $5,750
Savings
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Northeast Harbors Cruise

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
Activities
Wine Tasting
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
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from $13,440
Save 10%
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.
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