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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 4 unique Boston cultural experiences for 2026 or 2027. 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 Archaeological Site Visits, Local Market Visits, Wine Tasting, Urban Exploration, and Wildlife Viewing and cost from $6,350 for experiences of 9 to 14 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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Sailing in Boston
from $6,350
Savings
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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
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from $25,010
EXPLORE

Fall Foliage on the St. Lawrence with Smithsonian Journeys

Toronto - Boston - 13 Day Itinerary aboard Le Bellot
  • Sail the scenic St. Lawrence Seaway
  • Stroll Old Montreal streets
  • Explore Prince Edward Island
  • Experience the Acadian culture
  • Explore Nova Scotia and Lunenburg
Starts / Ends
Toronto / Boston
Activities
Whale Watching
Activity Level
Variable
Sail Canada’s St. Lawrence Seaway on a 13-day cruise aboard Le Bellot. Visit Toronto, Montreal, Quebec, Tadoussac, Charlottetown, Magdalen Islands, Sydney, Lunenburg, Portland, and Boston. Enjoy whale watching, historic tours, cultural experiences, scenic landscapes, and regional cuisine throughout this journey.
Cruise Details
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Explore beautiful and historic Montreal
from $13,830
No SS
EXPLORE

Fall Foliage on the St. Lawrence - with Smithsonian Journeys

Toronto to Boston - 14 Day Itinerary aboard Le Bellot
  • Sail the Saint Lawrence Seaway
  • Old Montreal exploration
  • Visit Quebec City's UNESCO district
  • See Lunenburg colonial charm
Starts / Ends
Toronto / Boston
Activities
Wildlife Viewing
Activity Level
Variable
Sail from Toronto to Boston on a 14-day Canadian cruise with Smithsonian Journeys aboard Le Bellot. Explore Montreal, Quebec City, Tadoussac, Nova Scotia towns, and the Magdalen Islands. Enjoy historic sites, coastal scenery, marine life, and cultural landmarks throughout this voyage.
Cruise Details
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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
Urban Exploration, Wine Tasting, Village Visits, Archaeological Site Visits, Local Market Visits
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
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We have had excellent results when working with Adventure Life. We've just set up out third trip with them because the first two were great! Adventure Life has always listened, worked with us, and set up trips the way we've wanted. They've also found experiences we wouldn't have known about otherwise, that have been some of the highlights of the entire trip.
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Mary goes the extra mile to ensure smooth travel booking and trips! She recommends amazing journeys at a great value!
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Shannon was always quick to reply to my questions and her honest answers helped us identify the right trip for us. Off to a great start!
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Adventure Life planned an extraordinary trip to Uruguay where we were able to see a colonial town, modern city, the coast life, and the countryside. They planned beautiful experiences such as olive oil and cheese tastings, and horseback riding through the country. The local tour company was excellent, all were so kind, knowledgable, and professional. We highly recommend Adventure Life, as we have had several fantastic experiences with them and this trip was no exception!
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