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Top Massachusetts Cruises & Trips

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Explore these 6 top Massachusetts cruises for 2023 and 2024. Some of the most popular activities on our Massachusetts trips include small ship cruises, cruises, village visits, wildlife viewing, and urban exploration. Discover Gloucester, Boston, Provincetown, and Martha's Vineyard with your expert local English-speaking guides who will show you the hot spots and the off-the-beaten-path hidden gems. We work with only the best small ships that carry under 500 fortunate guests, and we can give you unbiased advice to match you with the perfect ship and perfect cruise for your next vacation. Our Massachusetts cruises start from $4,689 for cruises of 10 to 16 days. Contact one of Adventure Life's Massachusetts cruise specialists for help planning a seamless trip.
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Visit Plymouth
$4,689
EXPLORE

Portland to Saint John

10 Day Itinerary aboard Ocean Navigator
  • Stroll the streets of Portland
  • Explore coastal towns
  • Discover the region's history
  • Appreciate art and local artists
Starts / Ends:
Portland / Rockland
Activities:
Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
Embark on a 10-day adventure aboard Ocean Navigator sailing from Portland, Maine to Saint John, New Brunswick, on a cruise route that guides travelers through highly sought-after towns and cities along the Eastern seaboard. Savor renowned lobster dishes, admire picturesque coastal towns, explore …
Cruise Details
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Visit historic Baltimore
$8,089
EXPLORE

Boston, MA to Nassau, Bahamas

Boston - Nassau - 16 Day Itinerary aboard Ocean Navigator
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts / Ends:
Boston / Nassau
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
This 16-day tour takes you from lively Boston to the beaches of Nassau aboard the Ocean Navigator. With stops in Baltimore, Charleston, West Palm Beach, and other towns, this itinerary allows you to experience the Eastern cities of the United States en route to The Bahamas.
Cruise Details
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$5,689
EXPLORE

Montreal to Gloucester

11 Day Itinerary aboard Ocean Navigator
  • Enjoy Montreal's ambiance
  • Cruise the scenic Strait of Canso
  • Visit Charlottetown
  • Discover the history of Halifax
Starts / Ends:
Montreal / Boston
Activities:
Small Ship Cruises, Village Visits, Wildlife Viewing
Activity Level:
Relaxed
Phenomenal experiences lay in store for those who choose this epic 11-day adventure. Relish the charms of Montreal on your pre-voyage hotel stay, then prepare to be dazzled as the ship gets underway. On this trip, a naturalist joins you onboard to enhance the sheer joy of gliding upon the St. …
Cruise Details
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Aerial view of New York City at dusk
$5,250
EXPLORE

New York, NY to Quebec City - Port to Port

11 Day Itinerary aboard Silver Shadow
  • Visit historic cities
  • Spot a variety of wildlife
  • Learn about Saguenay's heritage
  • Walk in Forillon National Park
Starts / Ends:
New York / Quebec City
Activities:
Kayaking, Small Ship Cruises, Wildlife Viewing
Activity Level:
Relaxed
Join Silver shadow on this 11-day voyage across New England. Along with seeing the stunning fall foliage along the North American coast, this spectacular voyage includes overnight stays in two of the biggest cities in the US. Start with the dazzling lights of New York City and go via the …
Cruise Details
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The Gully -Sable Island
$13,160
EXPLORE

Symphony on the St. Lawrence: From Québec to the Canadian Maritimes – with Smithsonian Journeys

Toronto - Gloucester - 15 Day Itinerary aboard Le Bellot
  • Visit Québec and Lunenburg
  • Discover the art of Montréal
  • Explore the beauty of nature
  • Enjoy musical performances
Starts / Ends:
Toronto / Gloucester
Activities:
Hiking, Small Ship Cruises, Wildlife Viewing
Activity Level:
Relaxed
Experience the unforgettable 15-day cruise exploration offered by Le Bellot, and enjoy the vast unspoiled expanses of Canada and the North American coast. Your journey will start in Toronto then you will enjoy a magnificent sail along the shimmering waters of Lake Ontario. Youwill then head …
Cruise Details
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Explore beautiful and historic Montreal
$12,230
EXPLORE

From Canada to the American East Coast

Toronto - Gloucester - 15 Day Itinerary aboard Le Dumont-d'Urville
  • Explore Montreal and Quebec City
  • Visit historic coastal villages
  • Learn about Canada's history
  • Admire the landscapes of the coast
Starts / Ends:
Toronto / Gloucester
Activities:
Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
Enjoy this 15-day cruise exploring Canada and the American East Coast from Toronto to Gloucester on board the luxurious Le Dumont-d'Urville. Explore the natural beauty and historic cities of the Saint Lawrence Seaway from the bustling city of Toronto. Cruise across Lake Ontario and through the …
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