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Colorful sunrise at Portland Head Lighthouse in Maine

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 6 tours hand-selected by the travel experts at Adventure Life. Explore the best of during September 2026 as you enjoy Archaeological Site Visits, Urban Exploration, Village Visits, Biking, and Local Market Visits. Prices for trips in September 2026 range from $7,070 to $14,025 for a vacation of 8 to 13 days. Choose any of the below 6 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 $7,070
Savings
EXPLORE

Yankee Seaports

Boston - New York - 8 Day Itinerary aboard American Glory
Starts / Ends
Boston / New York City
Activities
Local Market Visits, Wine Tasting
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 $8,675
Savings
EXPLORE

New England Islands

Providence Roundtrip - 8 Day Itinerary aboard American Liberty
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.
  • Enjoy Block Island's beaches
  • Explore Whaling Museum New Bedford
  • Discover Martha's Vineyard's towns
  • Learn whaling legacy and maritime
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $7,899
EXPLORE

All Five Great Lakes

Toronto to Chicago - 11 Day Itinerary aboard Victory I
Starts / Ends
Toronto / Chicago
Activities
Biking
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 $7,899
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
Starts / Ends
Toronto / Chicago
Activities
Archaeological Site Visits, Urban Exploration
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
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
Golden light over the Chicago skyline
from $7,899
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Sail from Chicago to Toronto aboard Victory II on an 11-day cruise, exploring the best of the Great Lakes. Discover a mix of vibrant cities, quiet natural beauty, historic landmarks, and cultural icons throughout this immersive Great Lakes journey.
  • Visit Chicago’s Art Institute
  • Sail scenic Lake Michigan
  • Discover Milwaukee city
  • Visit Niagara Falls
Cruise Details
0
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