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Top East Coast of US Trips & Tours in September 2026

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Discover East Coast of US in September 2026 on one of these 8 tours hand-selected by the travel experts at Adventure Life. Explore the best of during September 2026 as you enjoy Urban Exploration, Archaeological Site Visits, Local Market Visits, Whale Watching, and Wildlife Viewing. Prices for trips in September 2026 range from $5,760 to $13,665 for a vacation of 8 to 13 days. Choose any of the below 8 itineraries in September 2026 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
Sailing in Boston
from $7,235
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
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Enjoy scenic New England
from $8,475
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 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.
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,899
OBC
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
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.
Cruise Details
0
Mackinac Island, Michigan
from $7,899
OBC
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
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.
Cruise Details
0
Golden light over the Chicago skyline
from $7,899
OBC
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
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.
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
  • 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
Urban Exploration, Archaeological Site Visits
Activity Level
Variable
Set sail on a 13-day from Chicago to Montreal, experiencing the Great Lakes in style aboard the Victory I. Each day offers unique experiences, from scenic sailing to cultural explorations, making this a one-of-a-kind adventure through North America's freshwater treasures.
Cruise Details
0
Detroit, Michigan at Dusk
from $7,899
OBC
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
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.
Cruise Details
0
Boston's skyline and harbor
from $5,760
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, Wildlife Viewing, Whale Watching
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
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