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Colorful sunrise at Portland Head Lighthouse in Maine

Top East Coast of US Trips & Tours in September 2025

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Discover East Coast of US in September 2025 on one of these 11 tours hand-selected by the travel experts at Adventure Life. Explore the best of Chicago, Detroit, Lake Michigan, Cleveland, and Toronto during September 2025 as you enjoy cruises, small ship cruises, urban exploration, cultural, and archaeological site visits. Prices for trips in September 2025 range from $6,640 to $24,635 for a vacation of 8 to 15 days. Choose any of the below 11 itineraries in September 2025 and customize it when you contact one of Adventure Life's expert East Coast of US trip planners.
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    • East Coast of US
Vanderbilt Mansion National Historic Site
$7,235
Savings
EXPLORE

Hudson River Fall Foliage

New York Roundtrip - 8 Day Itinerary aboard American Glory
  • Visit the Kaaterskill Falls
  • Explore the New York State Museum
  • Enjoy cheese and apple tasting
  • Learn the marine history
Starts / Ends:
New York / New York
Activities:
Small Ship Cruises
Activity Level:
Variable
Embark on an 8-day Hudson River Fall Foliage cruise roundtrip from New York aboard American Glory. Experience the vibrant autumn colors along the Hudson River, surrounded by the Catskill Mountains and Taconic and Berkshire Hills. Explore historic ports of call with guided shore excursions to iconic …
Cruise Details
0
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
$6,640
Savings
EXPLORE

Maine Coast & Harbors Cruise

Roundtrip Portland - 8 Day Itinerary aboard American Glory
  • Visit Bucksport
  • Visit Camden in Maine
  • Visit Bar Harbor
  • Visit Cape Elizabeth
Starts / Ends:
Portland / Portland
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits, Wildlife Viewing
Activity Level:
Variable
On this 8-day Maine Coast & Harbors Cruise roundtrip Portland aboard the American Glory, explore Maine's breathtaking coastline, framed by a backdrop of mountains teeming with native wildlife. Immerse in the region's maritime heritage in a trip past the grand homes of sea captains and …
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
Enjoy scenic New England
$7,780
Savings
EXPLORE

New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty
  • Enjoy Block Island's beaches
  • Explore Whaling Museum New Bedford
  • Discover Martha's Vineyard's towns
  • Explore New Bedford's whaling
Starts / Ends:
Nantucket / Newport
Activities:
Village Visits
Activity Level:
Variable
Embark on an 8-day cruise through the maritime heritage of New England. Begin in Providence, Rhode Island, known as the "Renaissance City," boasting centuries of history reflected in its theaters, arts, and architecture. Next, delve into the whaling legacy of New Bedford, Massachusetts, …
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
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
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
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
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
1-11 of 11 Results
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