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Explore the rocky shores and clear waters of Lake Superior

Top Great Lakes Trips & Tours in September 2026

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Discover Great Lakes in September 2026 on one of these 9 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, Biking, Wildlife Viewing, and Local Market Visits. Prices for trips in September 2026 range from $7,899 to $50,860 for a vacation of 8 to 15 days. Choose any of the below 9 itineraries in September 2026 and customize it when you contact one of Adventure Life's expert Great Lakes trip planners.
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    • Great Lakes
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
  • Niagara Falls visit
  • See Cleveland Rock Hal
  • Observe Soo Locks transit
  • Mackinac Island cycling
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.
Cruise Details
0
Mackinac Island, Michigan
from $7,899
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Explore Navy Pier and city skyline
  • Visit Milwaukee craft breweries
  • Lake Michigan sailing
  • Enjoy Escanaba waterfront views
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day Great Lakes cruise aboard Victory II from Chicago to Toronto. Explore Detroit, Cleveland, Mackinac Island, Niagara Falls, and Milwaukee. Sail Lake Michigan, Huron, and Superior. Participate in cultural programs, enjoy scenic decks, and witness engineering marvels at the Soo Locks.
Cruise Details
0
See the mighty Niagara Falls
from $11,995
EXPLORE

Niagara and the Great Lakes

Toronto - Milwaukee - 8 Day Itinerary aboard Viking Great Lakes
  • Toronto Exploration
  • Explore Mackinac Island
  • Niagara Falls & Welland Canal
  • Point Pelee Birdwatching
  • Detroit’s Innovation Legacy
  • Alpena’s Maritime Adventures
  • Mackinac Island & Milwaukee’s Charm
Starts / Ends
Lake Ontario / Milwaukee
Activity Level
Variable
On this 8-day Niagara and the Great Lakes cruise from Toronto to Milwaukee aboard the Viking Great Lakes, explore nature and culture. Navigate the Welland Canal, witness Niagara Falls, and spot migratory birds at Point Pelee. Visit Detroit’s Henry Ford Museum, kayak in Alpena, tour Mackinac Island, and explore Milwaukee’s waterfront history.
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
  • See powerful Niagara Falls
  • Explore Cleveland’s rock history
  • Tour Milwaukee’s lakefront gems
  • Visit peaceful Mackinac Island
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.
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
  • Cruise all five Great Lakes
  • Visit Niagara Falls up close
  • Tour Cleveland’s museums
  • Visit Mackinac Island
Starts / Ends
Toronto / Chicago
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 Details
0
Historic, car-free island with lake views in Mackinac Island, Michigan
from $12,995
EXPLORE

Great Lakes Treasures

Milwaukee to Milwaukee - 10 Day Itinerary aboard Viking Great Lakes
  • Stroll Milwaukee RiverWalk
  • Ride Mackinac Island Carriage
  • Explore shipwrecks & cliffs
  • Discover Soo Locks History
Starts / Ends
Milwaukee / Milwaukee
Activities
Urban Exploration, Village Visits, Wildlife Viewing, Kayaking, Hiking, Wine Tasting, Fishing, Citizen Science, Scuba Diving
Activity Level
Variable
Discover the treasures of the Great Lakes on a 10-day Viking cruise, from Milwaukee’s RiverWalk and Mackinac Island’s timeless charm to kayaking Killarney’s lakes and exploring the shipwrecks of Fathom Five. End in Chicago after hiking, wine tasting, and uncovering rich history, natural beauty, and culture along the way.
Cruise Details
0
Enjoy stunning views of Niagara Falls
from $9,499
EXPLORE

Five Great Lakes and St. Lawrence Seaway

Chicago to Quebec - 15 Day Itinerary aboard Victory II
  • Cruise scenic Lake Huron
  • Explore old Montreal
  • Experience Detroit’s rich heritage
  • Witness Soo Locks engineering
Starts / Ends
Chicago / Quebec City
Activities
Archaeological Site Visits, Local Market Visits
Activity Level
Variable
Sail from Chicago to Quebec on a 15-day cruise through the Great Lakes and St. Lawrence Seaway aboard Victory II. Visit iconic destinations like Mackinac Island, Niagara Falls, and Montreal. Explore vibrant cities, historic sites, and scenic waterways.
Cruise Details
0
Explore Toronto
from $7,899
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory I
  • Explore Mackinac Island by bike
  • Lake Huron sailing
  • Learn Detroit creative revival
  • Experience Niagara Falls
Starts / Ends
Chicago / Toronto
Activities
Biking
Activity Level
Variable
Sail the Great Lakes on an 11-day cruise aboard Victory I, exploring Chicago, Milwaukee, Mackinac Island, Detroit, Cleveland, Niagara Falls, and Toronto. You experience historic locks, island cycling, cultural cities, and scenic lake passages across interconnected inland seas.
Cruise Details
0
from $13,480
$1000 SBC
EXPLORE

Fall Foliage on the St. Lawrence: Quebec to the Canadian Maritimes – with Smithsonian Journeys

Toronto - Boston - 13 Day Itinerary aboard Le Bellot
  • Sail the scenic St. Lawrence Seaway
  • Visit Montreal, a cosmopolitan city
  • Explore Prince Edward Island
  • Experience the Acadian culture
  • Explore Nova Scotia and Lunenburg
Starts / Ends
Toronto / Boston
Activity Level
Variable
Explore eastern Canada and New England on a 13-day Smithsonian Journeys cruise. Sail from Toronto to Boston with stops in Quebec, PEI, Nova Scotia, and Cape Cod. Highlights include Montreal, Tadoussac, Magdalen Islands, Charlottetown, and Lunenburg. Includes expert talks and a shore excursion in each port.
Cruise Details
0
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Eric N.
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