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Colorful sunrise at Portland Head Lighthouse in Maine

East Coast Urban Exploration Cruises

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Discover the wonders of the East Coast of the United States on our 23 exceptional urban exploration city tours for 2025. With Adventure Life's city tours, you can explore captivating destinations like Portland, Maine, Chicago, and Montreal, all while embarking on remarkable small ship cruises that guide you through charming coastal towns and cities. From savoring renowned lobster dishes to admiring picturesque coastal landscapes and exploring historic landmarks, our tours offer a diverse range of activities suitable for all travelers. Whether you're looking to stroll the streets of Portland or witness the thundering Niagara Falls, our city tours promise an unforgettable journey filled with cultural immersion and urban exploration. Prices starting at $5,999 to $54,870. Join us on a trip to create lasting memories and uncover the hidden gems of the East Coast - contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • East Coast of US
Visit Plymouth
from $13,940
Savings
EXPLORE

Grand New England Cruise

Roundtrip Boston - 15 Day Itinerary aboard American Patriot
Starts / Ends
Boston / Boston
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.
  • Explore Portland iconic lighthouses
  • Discover Bath historic shipyards
  • Explore Bangor Victorian mansions
  • Discover Portsmouth architecture
Cruise Details
0
Eastern Point Lighthouse, Gloucester, Massachusetts
from $11,030
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Independence
Starts / Ends
Portland / New York
Activity Level
Variable
Cruise the New England coast on a 16-day cruise from Portland to New York aboard American Independence. This journey delivers history, culture, and natural beauty through iconic destinations, guided tours, and onboard enrichment—all while experiencing the region’s fall colors and crisp sea air.
  • View Cape Elizabeth lighthouses
  • Discover Nantucket whaling history
  • Walk Portland’s Old Port
  • Visit Maine Maritime Museum
Cruise Details
0
Visit Portsmouth
from $13,285
Savings
EXPLORE

New England Fall Foliage Cruise

Portland - New York - 16 Day Itinerary aboard American Glory
Starts / Ends
Portland / New York
Activities
Wine Tasting
Activity Level
Variable
Sail the coast of New England on a 16-day New England Fall Foliage cruise aboard American Glory, visiting historic cities and scenic harbors from Maine to New York. This cruise blends history, coastal charm, and iconic landmarks with smooth sailing and guided excursions.
  • Walk Portland’s working waterfront
  • Tour Newport’s seaside mansions
  • Walk at cobblestone streets
  • Visit Gloucester’s Maritime Museum
Cruise Details
0
Beautiful seascapes in Maine
from $6,710
Savings
EXPLORE

Maine Coast & Harbors Cruise

Portland - Bangor - 9 Day Itinerary aboard American Glory
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.
  • Cruise through Casco Bay
  • Sample fresh oysters in Bath
  • Visit Boothbay Harbor's garden
  • Taste a traditional lobsterbake
Cruise Details
0
Vanderbilt Mansion National Historic Site
from $7,070
Savings
EXPLORE

Hudson River Fall Foliage

New York - New York - 8 Day Itinerary aboard American Glory
Starts / Ends
New York / Catskill
Activities
Village Visits
Activity Level
Variable
Embark on a scenic Hudson River 8-day cruise from New York to Albany aboard American Glory. Visit historic sites in Sleepy Hollow, West Point, Kingston, Hyde Park, and Catskill. Enjoy scenic views, onboard enrichment, and cultural landmarks. Experience the beauty and history of the Hudson River on this unforgettable journey.
  • Visit Sleepy Hollow landmarks
  • Tour West Point Academy
  • Discover Hyde Park’s history
  • Admire Vanderbilt Mansion
Cruise Details
0
Sailing in Boston
from $6,350
Savings
EXPLORE

Yankee Seaports

Boston - New York - 8 Day Itinerary aboard American Glory
Starts / Ends
Boston / New York City
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.
  • Visit the Massachusetts Maritime
  • Explore the Mystic Seaport Museum
  • Travel to Old Saybrook
  • Stroll around Sag Harbor
Cruise Details
0
Enjoy scenic New England
from $7,790
Savings
EXPLORE

New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty
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.
  • Enjoy Block Island's beaches
  • Explore Whaling Museum New Bedford
  • Discover Martha's Vineyard's towns
  • Learn whaling legacy and maritime
Cruise Details
0
Aerial view of New York City at dusk
from $8,600
EXPLORE

Montreal to New York, NY

Montreal - New York - 12 Day Itinerary aboard Silver Shadow
Starts / Ends
Montreal / New York City
Activities
Whale Watching, Wildlife Viewing, Kayaking
Activity Level
Variable
Embark on a 12-day cruise from Montreal to New York on the Silver Shadow, exploring Canada's Atlantic coast and New England's charm. Highlights include Quebec City, Prince Edward Island, and excursions like hikes and heritage walks, offering a blend of culture and relaxation.
  • Discover Montreal’s landscape
  • Explore Quebec City historic charm
  • Experience Saguenay’s wilderness
  • Stroll Charlottetown’s streets
Cruise Details
0
Explore beautiful Montreal
from $7,299
EXPLORE

New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
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.
  • Explore Portland
  • Watch whales in Saguenay Fjords
  • Walk Old Quebec streets
  • Explore Charlottetown history
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
Starts / Ends
Toronto / Boston
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.
  • Sail the scenic St. Lawrence Seaway
  • Visit Montreal, a cosmopolitan city
  • Visit Old Quebec, a UNESCO site
  • Colonial seaport of Charlottetown
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,299
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day Great Lakes cruise from Chicago to Toronto aboard Victory I, exploring cities, islands, and historical sites. Enjoy scenic sailings and unique excursions.
  • Discover Michigan's Upper Peninsula
  • Explore Detroit's Henry Ford Museum
  • Stroll Chicago’s Navy Pier
  • Visit Niagara Falls up close
Cruise Details
0
Visit historic locations along the shores of the Great Lakes
from $7,299
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise aboard Victory II, visiting iconic cities such as Chicago, Detroit, and Toronto. Discover scenic wonders like Mackinac Island and Niagara Falls, exploring rich history and culture along the way.
  • Visit car-free Mackinac Island
  • Sail through the Soo Locks
  • Explore the Henry Ford Museum
  • Visit Escanaba's lighthouse
Cruise Details
0
Golden light over the Chicago skyline
from $7,299
EXPLORE

All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I
Starts / Ends
Toronto / Chicago
Activities
Biking, Local Market Visits
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard Victory I, exploring vibrant cities and stunning natural landscapes. Enjoy historical tours and scenic sailing on this unique cruise through the heart of North America.
  • Discover the diverse food scene
  • Enjoy the vibrant nightlife
  • Visit Niagara Falls
  • Explore Niagara Peninsula
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $6,799
EXPLORE

All Five Great Lakes

Toronto to Chicago - 11 Day Itinerary aboard Victory I
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Cruise the Great Lakes from Toronto to Chicago on an 11-day cruise aboard Victory I. Explore museums, historic districts, and natural wonders while enjoying relaxing scenic days at sea.
  • See powerful Niagara Falls
  • Explore Cleveland’s rock history
  • Tour Milwaukee’s lakefront gems
  • Visit peaceful Mackinac Island
Cruise Details
0
Relax on the shores of the Great Lakes
from $6,799
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
Starts / Ends
Toronto / Chicago
Activities
Urban Exploration, Archaeological Site Visits
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise aboard Victory II and explore cultural hubs like Cleveland and Detroit, visit Niagara Falls, and relax on car-free Mackinac Island. Enjoy scenic days on Lake Ontario, Erie, Huron, Michigan, and Superior.
  • Cruise all five Great Lakes
  • Visit Niagara Falls up close
  • Tour Cleveland’s museums
  • Visit Mackinac Island
Cruise Details
0
Detroit, Michigan at Dusk
from $7,299
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Set sail on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard a Victory II. Explore Toronto, Niagara Falls, Cleveland, Detroit, and Mackinac Island, experiencing unique landmarks and vibrant cultures.
  • Explore Toronto
  • Experience Niagara Falls
  • Visit Henry Ford Museum
  • Enjoy a horse-drawn carriage tour
Cruise Details
0
Enjoy the scenery of the Great Lakes
from $7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Chicago - Montreal - 13 Day Itinerary aboard Victory I
Starts / Ends
Chicago / Montreal
Activity Level
Variable
Sail from Chicago to Montreal on a 13-day cruise aboard Victory I, exploring iconic cities, engineering marvels, and natural wonders. Scenic lake crossings offer time to unwind between dynamic destinations.
  • Visit Willis Tower in Chicago
  • Explore the Henry Ford Museum
  • Visit Rock and Roll Hall of Fame
  • Discover Toronto's culture
Cruise Details
0
Stunning Niagara Falls
from $7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Montreal - Chicago - 13 Day Itinerary aboard Victory I
Starts / Ends
Montreal / Chicago
Activity Level
Variable
Embark on an unforgettable 13-day cruise from Montreal to Chicago aboard the Victory I, exploring all five Great Lakes. This voyage combines scenic sailing with onshore excursions, offering a unique blend of urban exploration and natural wonders.
  • Discover the city of Toronto
  • Visit the Henry Ford Museum
  • Visit Lake Huron
  • Savor local delicacies
Cruise Details
0
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