Have questions? We're here.
Springtime in Boston

New England Urban Exploration Cruises

Travel made your way
Talk with an expert
Build your ideal New England trip. Call 1.406.541.2677
Start Planning My Trip
Explore the charming cityscapes and vibrant culture of New England on our 8 exceptional urban exploration tours for 2025. Surrounded by rich history, breathtaking landscapes, and quaint coastal towns, our New England city tours provide a deep dive into the heart of this remarkable region. Over 8 to 15 days, you will discover the allure of New England, from the stunning beauty of Lake Michigan to the thundering Niagara Falls and the historic maritime city of Montreal. Delight in renowned lobster dishes, explore picturesque towns, and appreciate the arts and local artists along the eastern seaboard. To embark on a journey that uncovers the magic of New England's urban environments and hidden gems, contact one of Adventure Life's tour specialists for help planning your next seamless trip.
Filter (8 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • New England
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
Beautiful seascapes in Maine
from $6,710
Savings
EXPLORE

Maine Coast & Harbors Cruise

Portland - Bangor - 9 Day Itinerary aboard American Glory
  • Cruise through Casco Bay
  • Sample fresh oysters in Bath
  • Visit Boothbay Harbor's garden
  • Taste a traditional lobsterbake
Starts / Ends
Portland / Bar Harbor
Activity Level
Variable
Cruise Maine’s coast for 9 days aboard American Glory. Sail Casco Bay, visit a Bath oyster farm, explore Boothbay’s gardens, enjoy a Rockland lobsterbake, tour Acadia National Park in Bar Harbor, and walk its quaint downtown. In Castine, learn its Revolutionary War history, and finish in Bangor, Stephen King’s hometown and inspiration for Derry.
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
Wildlife Viewing, Village Visits
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
Golden light over the Chicago skyline
from $4,999
EXPLORE

Montreal to Portland

10 Day Itinerary aboard Victory I
  • Explore Montreal's European charm
  • Visit Halifax’s Citadel Hill
  • Stroll Portland’s historic streets
  • Enjoy a scenic whale-watching
Starts / Ends
Montreal / Portland
Activities
Archaeological Site Visits, Urban Exploration, Whale Watching
Activity Level
Variable
Set sail on a 10-day cruise from Montreal to Portland aboard the Voyager I. Experience Montreal’s European charm and explore Quebec City’s historic streets. Enjoy whale-watching in Saguenay Fjord and discover Charlottetown’s coastal beauty. Sail through the Strait of Canso, visit Halifax’s bustling waterfront, and conclude in vibrant Portland, Maine, where arts and seafood await.
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
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
1-8 of 8 Results
  • 1

Top New England Travel Destinations

New England Trips by Departure Date

New England Trips by Duration

New England Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By