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Top New England Tours & Cruises in 2027

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Discover the best the world has to offer with Adventure Life’s expert-curated New England tours 2027. From Portland, Boston, Newport, and Provincetown to hidden gems off the beaten path, our 5 top-rated itineraries take you deep into New England’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 9 to 13 days itineraries starting at $6,350 to $54,390. You’ll find options that suit your travel style. Whether you’re passionate about Urban Exploration, Archaeological Site Visits, Whale Watching, Wildlife Viewing, and Village Visits or eager to explore New England’s rich culture and natural beauty, our New England tours 2027 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 New England tour 2027 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 New England tour 2027. 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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    • New England
Sailing in Boston
from $6,350
Savings
EXPLORE

Northeast Harbors Cruise

Boston - New York - 9 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
Wine Tasting, Local Market Visits
Activity Level
Variable
Join this 9-day Northeast Harbors 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
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from $13,440
$1000 SBC
EXPLORE

Fall Foliage on the St. Lawrence: Quebec to the Canadian Maritimes – with Smithsonian Journeys

Toronto - Boston - 13 Day Itinerary aboard Le Bellot
  • Sail the scenic St. Lawrence Seaway
  • Visit Montreal, a cosmopolitan city
  • Explore Prince Edward Island
  • Experience the Acadian culture
  • Explore Nova Scotia and Lunenburg
Starts / Ends
Toronto / Boston
Activities
Village Visits
Activity Level
Variable
Explore eastern Canada and New England on a 13-day Smithsonian Journeys cruise. Sail from Toronto to Boston with stops in Quebec, PEI, Nova Scotia, and Cape Cod. Highlights include Montreal, Tadoussac, Magdalen Islands, Charlottetown, and Lunenburg. Includes expert talks and a shore excursion in each port.
Cruise Details
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Visit Portsmouth
from $7,299
Save $6600
EXPLORE

New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
  • Explore Portland
  • Watch whales in Saguenay Fjords
  • Walk Old Quebec streets
  • Explore Charlottetown history
Starts / Ends
Portland / Toronto
Activity Level
Variable
Experience a 12-day cruise from Portland to Toronto aboard Victory I and enjoy coastal views, local cuisine, and relaxing days at sea. This immersive journey blends Canadian culture, maritime history, and scenic waterways for a unique small-ship cruising experience.
Cruise Details
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Aerial View of Halifax Skyline
from $8,299
EXPLORE

New England and Canada

Montreal to Portland - 13 Day Itinerary aboard Victory I
  • Visit UNESCO-listed Old Quebec City
  • Charlottetown historic charm
  • Learn Yarmouth’s Acadian heritage
  • Sail through Saguenay Fjord
Starts / Ends
Montreal / Portland
Activity Level
Variable
Begin the 13-day voyage in Montreal with a hotel stay, then board Victory I and cruise through Quebec City, Saguenay Fjord, Charlottetown, Halifax, and Yarmouth before ending in Portland, Maine. Sail the Gulf of St. Lawrence and Strait of Canso while exploring historic towns, coastal villages, and maritime landmarks across Atlantic Canada.
Cruise Details
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Colorful sunrise at Portland Head Lighthouse in Maine
from $8,299
EXPLORE

New England and Canada

Montreal to Portland - 13 Day Itinerary aboard Victory II
  • Walk Quebec City's Old Town streets
  • Saguenay Fjord sailing
  • Gulf crossing experience
  • Tour Halifax historic citadel
Starts / Ends
Montreal / Portland
Activities
Urban Exploration, Archaeological Site Visits, Whale Watching, Wildlife Viewing
Activity Level
Variable
Begin your 13-day voyage in Montreal with a hotel stay, then board Victory II and sail the St. Lawrence River to Quebec City, Saguenay, Baie-Comeau, and Gaspe. Cross the Gulf of St. Lawrence to Charlottetown, continue to Halifax and Yarmouth, and finish in Portland, Maine. Explore fortified cities, fjords, island capitals, and working waterfronts.
Cruise Details
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