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Boston's skyline and harbor

Top Massachusetts Tours & Cruises in 2025

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Discover Massachusetts in 2025 on one of these trips hand selected by the travel experts at Adventure Life. Select any of the below 4 top-rated trips where you will explore Boston, Martha's Vineyard, Gloucester, and Nantucket with an exceptional bilingual guide on a small group or customizable private tour. The most popular things to do in Massachusetts in are cruises, small ship cruises, cultural, village visits, and land & sea exploration. Our Massachusetts trips in 2025 range in price from $5,145 to $24,635 for trips of 8 to 15 days. Contact one of Adventure Life's expert Massachusetts trip planners for help planning a seamless experience.
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    • Massachusetts
Enjoy scenic New England
$7,780
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
Activities:
Village Visits
Activity Level:
Variable
Embark on an 8-day cruise through the maritime heritage of New England. Begin in Providence, Rhode Island, known as the "Renaissance City," boasting centuries of history reflected in its theaters, arts, and architecture. Next, delve into the whaling legacy of New Bedford, Massachusetts, …
Cruise Details
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Visit Portsmouth
$13,155
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, 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
Eastern Point Lighthouse, Gloucester, Massachusetts
$10,835
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, Village Visits
Activity Level:
Variable
Experience a15-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
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, 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
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