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Massachusetts Small Ship Cruises

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Experience the charm and history of the Eastern seaboard with Adventure Life's array of small ship cruises for 2025. Join us on a cruise journey from Portland, Maine to Saint John, New Brunswick, where travelers can explore coastal towns, appreciate local art, and delve into the region's rich history. Savor delicious lobster dishes, wander through picturesque villages, and immerse yourself in urban exploration. Whether you choose the Montreal to Gloucester route, with stops in Charlottetown and Halifax, or opt for the voyage from New York to Quebec City, spotting wildlife and kayaking along the way, each 11-day adventure promises phenomenal experiences. For a longer trip, embark on a 15-day cruise aboard Le Bellot, from Toronto to Boston, to discover the art of Montréal, the beauty of the Canadian Maritimes, and enjoy musical performances. With prices starting at $5,145 to $54,870, don't miss the chance to sail along the North American coast and contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Massachusetts
Visit Plymouth
$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, Urban Exploration, Village Visits
Activity Level:
Variable
Embark on a 15-day cruise to and from Boston aboard the American Patriot. Explore historic waterways, uncovering America's rich past. Visit seaport towns like Portland and Newport, explore iconic shipyards, and enjoy a traditional Maine lobster bake. Experience the charm and history of New …
Cruise Details
0
Visit Portsmouth
$13,155
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 15 Day Itinerary aboard American Glory
  • Visit Portsmouth and Gloucester
  • Explore Martha’s Vineyard & Newport
  • Explore Sag Harbor
  • Discover Mystic Seaport
Starts / Ends:
Portland / New York City
Activities:
Adventure Options, Land & Sea Exploration, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Experience an adventure through New England's picturesque waterways, adorned with vibrant autumn hues. Encounter stunning natural scenery and historic shipbuilding traditions along Maine's coast, followed by exploration of iconic destinations like Martha’s Vineyard and Newport. …
Cruise Details
0
Sailing in Boston
$6,640
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
Activities:
Local Market Visits, Small Ship Cruises, Urban Exploration, Whale Watching, Wildlife Viewing
Activity Level:
Variable
Set sail on an 8-day Yankee Seaports cruise, sailing from Boston to New York aboard American Glory. This scenic journey takes you through the best seaport towns of the Northeast and learn about the historic neighborhoods of Boston.

Visit the picturesque coastal town of Plymouth, MA, and experience …
Cruise Details
0
Explore beautiful and historic Montreal
$15,360
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:
River Cruises, Small Ship Cruises, Urban Exploration, Village Visits, Wildlife Viewing
Activity Level:
Variable
On this 15-day Fall Foliage on the St. Lawrence cruise from Toronto to Boston aboard Le Champlain, navigate the waterways of eastern Canada and northern New England, known for their beautiful coastlines, cliffs, and waterfront villages. Start by sailing the St. Lawrence Seaway to cities like …
Cruise Details
0
Eastern Point Lighthouse, Gloucester, Massachusetts
$10,835
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 15 Day Itinerary aboard American Independence
  • Visit Portsmouth and Gloucester
  • Explore Martha’s Vineyard & Newport
  • Explore Sag Harbor
  • Discover Mystic Seaport
Starts / Ends:
Portland / New York City
Activities:
Adventure Options, Land & Sea Exploration, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Experience a 15-day New England Fall Foliage Cruise from Portland to New York aboard American Independence. Through New England's picturesque waterways, adorned with vibrant autumn hues. Encounter stunning natural scenery and historic shipbuilding traditions along Maine's coast, followed by …
Cruise Details
0
Boston's skyline and harbor
$5,145
Savings
EXPLORE

Yankee Seaports

8 Day Itinerary aboard American Independence
  • Visit the Massachusetts Maritime
  • Explore the Mystic Seaport Museum
  • Travel to Old Saybrook
  • Stroll around Sag Harbor
Starts / Ends:
Boston / New York
Activities:
Local Market Visits, Small Ship Cruises, Urban Exploration, Whale Watching, Wildlife Viewing
Activity Level:
Variable
Set sail on an 8-day Yankee Seaports cruise, sailing from Boston to New York aboard American Independence. This scenic journey takes you through the best seaport towns of the Northeast and learn about the historic neighborhoods of Boston.

Visit the picturesque coastal town of Plymouth, MA, and …
Cruise Details
0
1-6 of 6 Results
TrustScore 4.8 | 417 reviews
TrustScore 4.8 of 5
total score
Based on 417 reviews on
review score
4 hours ago
Adventure Life has been great throughout my planning process for our up and coming Galapagos cruise. Kevin Moore, in particular, was very helpful in assisting me in making choices and providing me with options. He was also very patient, as I worked through figuring out what I really wanted in this vacation.
Lucy Greenway
review score
4 hours ago
Adventure Life was a pleasure to work with. They helped us find different options for our charter and answered a lot of questions with patience and clarity.
Brooke Hopper
review score
1 day ago
Excellent service, great hotels and well organized excursions with expert guides! Highly recommended!
Shadi Dalili
review score
2 days ago
Clara Tort has been our Travel Advisor for Buenos Aires, then for Iguazu, then for Mendoza and Aconcagua Trekking, and then for Patagonia and Fitz Roy trekking. She has navigated with us through our travels, and now we are coming back for more- onto Machu Pichu and Peru.
Gus ORDONEZ
review score
2 days ago
Mary Curry made the experience wonderful for the second time. She is the reason we returned to Adventure Life to book our second cruise on WindStar. She is tireless, well informed, pleasant to work with and totally reliable. If you offer employees bonuses, give her one! there who answered to phone to help us book shore excursions were also very good and easy to work with - and we demand rather an lot of help.
Laura Flanagan

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