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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 14 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 $4,999 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
$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, Urban Exploration, Village Visits
Activity Level:
Variable
Embark on a 15-day cruise to and from Boston aboard the American Patriot. Explore historic waterways, uncovering America's rich past. Visit seaport towns like Portland and Newport, explore iconic shipyards, and enjoy a traditional Maine lobster bake. Experience the charm and history of New …
Cruise Details
0
Beautiful seascapes in Maine
$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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits, Wildlife Viewing
Activity Level:
Variable
On this 9-day Maine Coast & Harbors Cruise from Portland to Bangor aboard the American Glory, sail through Portland Harbor into Casco Bay, watching for seals and taking in lighthouses, islands, and forts along the coast. In Bath, visit a family-owned oyster farm to learn about oyster …
Cruise Details
0
Visit Portsmouth
$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
Activities:
Adventure Options, Land & Sea Exploration, Small Ship Cruises, Urban Exploration, 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
Sailing in Boston
$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
Activities:
Local Market Visits, Small Ship Cruises, Urban Exploration, Whale Watching, Wildlife Viewing
Activity Level:
Variable
Set sail on an 8-day Yankee Seaports cruise, sailing from Boston to New York aboard American Glory. 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 experience …
Cruise Details
0
Explore beautiful and historic Montreal
$14,500
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:
River Cruises, Small Ship Cruises, Urban Exploration, Village Visits, Wildlife Viewing
Activity Level:
Variable
On this 15-day Fall Foliage on the St. Lawrence cruise from Toronto to Boston aboard Le Champlain, navigate the waterways of eastern Canada and northern New England, known for their beautiful coastlines, cliffs, and waterfront villages. Start by sailing the St. Lawrence Seaway to cities like …
Cruise Details
0
Mackinac Island, Michigan
$6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Visit car-free Mackinac Island
  • Sail through the Soo Locks
  • Explore the Henry Ford Museum
  • Visit Niagara Falls
Starts / Ends:
Chicago / Toronto
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Embark on an unforgettable 11-day cruise through the Great Lakes, starting from Chicago’s Navy Pier. Sail aboard Victory II, experiencing iconic destinations like Mackinac Island, Detroit, Cleveland, and Niagara Falls. This unique voyage offers a blend of vibrant city life, stunning natural …
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
$6,799
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
  • Discover Michigan's Upper Peninsula
  • Explore Detroit's Henry Ford Museum
  • Explore Manitoulin
  • Visit Niagara Falls up close
Starts / Ends:
Chicago / Toronto
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Embark on an unforgettable 11-day 5 Great Lakes cruise aboard Victory I, starting in Chicago and ending in Toronto. Stay at a hotel in Chicago before setting sail from Navy Pier. Explore vibrant cities like Detroit and Cleveland, marvel at the natural beauty of Mackinac Island, and witness the …
Cruise Details
0
Golden light over the Chicago skyline
$6,799
EXPLORE

All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I
  • Discover the diverse food scene
  • Enjoy the vibrant nightlife
  • Visit Niagara Falls
  • Explore Niagara Peninsula
Starts / Ends:
Toronto / Chicago
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Begin your 11-day All Five Great Lakes cruise in Toronto, exploring the CN Tower and Royal Ontario Museum. Experience Niagara Falls and the charm of Niagara-on-the-Lake. In Cleveland, visit the Rock and Roll Hall of Fame and West Side Market. Discover Detroit’s history at the Henry Ford …
Cruise Details
0
Stunning Niagara Falls
$7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Montreal - Chicago - 13 Day Itinerary aboard Victory I
  • Discover the city of Toronto
  • Visit the Henry Ford Museum
  • Visit Lake Huron
  • Savor local delicacies
Starts / Ends:
Montreal / Chicago
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Set sail on a 13-day cruise aboard the Victory II, starting in Montreal and ending in Chicago, as you travel through all five Great Lakes. Begin by exploring the cultural richness of Montreal and Toronto before witnessing the breathtaking power of Niagara Falls. Navigate through the historic …
Cruise Details
0
Enjoy the scenery of the Great Lakes
$7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Chicago - Montreal - 13 Day Itinerary aboard Victory I
  • Visit Willis Tower in Chicago
  • Explore the Henry Ford Museum
  • Visit Rock and Roll Hall of Fame
  • Discover Toronto's culture
Starts / Ends:
Chicago / Montreal
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Embark on a 13-day cruise from Chicago to Montreal aboard Victory II, exploring key landscapes and landmarks of the Great Lakes. Start in Chicago, visiting vibrant neighborhoods and notable sites like the Willis Tower. Cruise through Lake Michigan to destinations like Escanaba, Michigan, and …
Cruise Details
0
Golden light over the Chicago skyline
$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:
Toronto / Portland
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Whale Watching
Activity Level:
Variable
Embark on a 10-day cruise from Montreal to Portland aboard the Voyager I. Experience Montreal’s European charm, featuring historic architecture and vibrant arts. Explore landmarks like Mount Royal Park and Notre Dame Basilica. Visit Quebec City, a UNESCO World Heritage site known for its …
Cruise Details
0
Detroit, Michigan at Dusk
$6,799
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
  • Explore Toronto
  • Experience Niagara Falls
  • Visit Henry Ford Museum
  • Enjoy a horse-drawn carriage tour
Starts / Ends:
Toronto / Chicago
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Experience an 11-day cruise through the majestic Great Lakes aboard Victory II, beginning in Toronto. Explore the wonders of Niagara Falls, Cleveland, Detroit, and Mackinac Island. Sail through Lakes Ontario, Erie, Huron, Superior, and Michigan, each offering scenic beauty and historical …
Cruise Details
0
Eastern Point Lighthouse, Gloucester, Massachusetts
$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, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Experience a 15-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
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
Activities:
Local Market Visits, Small Ship Cruises, Urban Exploration, 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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