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Zakim Bridge reflection on the Charles River in Boston

Boston Trips with Village Visits

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Explore remote villages on one of the below 3 unique Boston cultural experiences for 2025 or 2026. 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 Urban Exploration, Archaeological Site Visits, Local Market Visits, Wildlife Viewing, and Wine Tasting and cost from $5,750 for experiences of 8 to 13 days. Tell us about your ideal Boston cultural trip and our Boston experts will help you plan every detail of your next trip.
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Edgartown on Martha's Vineyard
from $10,170
Savings
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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.
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Sailing in Boston
from $5,750
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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.
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from $13,440
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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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