Have questions? We're here.
Boston's skyline and harbor

Massachusetts Small Ship Cruises

Travel made your way
Talk with an expert
Build your ideal United States trip. Call 1.406.541.2677
Start Planning My Trip
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.
Filter (6 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Massachusetts
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
Activities
Local Market Visits
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
Visit Portsmouth
from $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
Activity Level
Variable
On this 15-day New England Fall Foliage Cruise from Portland to New York aboard American Glory, explore New England's waterways adorned with fall foliage, and natural landscapes. Visit towns, villages, and estates, all curated with experiences. Conclude with a cruise around the Statue of Liberty against the New York City skyline.
Cruise Details
0
Sailing in Boston
from $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
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 $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
  • 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
Urban Exploration, Village Visits, Wildlife Viewing
Activity Level
Variable
On this 15-day Fall Foliage cruise from Toronto to Boston aboard Le Champlain, explore the stunning coastlines of eastern Canada and northern New England. Sail the St. Lawrence Seaway, visiting cities like Montréal, Québec City, and Charlottetown. Discover Nova Scotia's history in Baddeck, Louisbourg, and Lunenburg before concluding in Boston.
Cruise Details
0
Eastern Point Lighthouse, Gloucester, Massachusetts
from $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
Activity Level
Variable
On this 15-day New England Fall Foliage Cruise from Portland to New York aboard American Independence, explore New England's waterways adorned with fall foliage, and natural landscapes. Visit towns, villages, and estates, all curated with experiences. Conclude with a cruise around the Statue of Liberty against the New York City skyline.
Cruise Details
0
Boston's skyline and harbor
from $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
Whale Watching
Activity Level
Variable
Join this 8-day Yankee Seaports cruise from Boston to New York aboard American Independence. 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
1-6 of 6 Results
  • 1

United States Travel Guide

Top United States Travel Destinations

United States Trips by Departure Date

Top Experiences in United States

United States Trips by Duration

United States Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By