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Top Massachusetts Tours & Cruises in 2025

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Discover the best the world has to offer with Adventure Life’s expert-curated Massachusetts tours 2025. From Boston, Martha's Vineyard, Gloucester, Nantucket, and Provincetown to hidden gems off the beaten path, our 6 top-rated itineraries take you deep into Massachusetts’s breathtaking landscapes. Guided by bilingual experts, these immersive experiences cater to adventurers seeking unique journeys in small groups or customizable private tours.

Choose from a variety of 8 to 15 days itineraries starting at $5,145 to $54,870. You’ll find options that suit your travel style. Whether you’re passionate about Urban Exploration, Village Visits, Adventure Options, Land & Sea Exploration, and Local Market Visits or eager to explore Massachusetts’s rich culture and natural beauty, our Massachusetts tours 2025 deliver unforgettable moments. Each itinerary blends awe-inspiring exploration with a commitment to sustainability to ensure your adventure supports the preservation of our planet.

Adventure Life’s dedication to personalized travel promises your Massachusetts tour 2025 is seamless from start to finish. From arranging transportation to selecting accommodations tailored to your preferences, we’ll take care of every detail. Our expert recommendations and insider tips make your journey even more enriching.

Contact our specialists today to start planning your Massachusetts tour 2025. Whether you’re a solo traveler, a couple, or part of a group, Adventure Life will create a transformative experience you’ll treasure forever.
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    • 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
Enjoy scenic New England
from $7,780
Savings
EXPLORE

New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty
  • Enjoy Block Island's beaches
  • Explore Whaling Museum New Bedford
  • Discover Martha's Vineyard's towns
  • Explore New Bedford's whaling
Starts / Ends
Nantucket / Newport
Activity Level
Variable
Embark on an 8-day cruise aboard American Liberty through New England, exploring maritime history from Providence to Newport. Indulge in lobster bakes, visit whaling museums, and wander charming cobblestone streets.
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
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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
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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
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