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Top Great Lakes Trips & Tours in September 2025

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Discover Great Lakes in September 2025 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of Mackinac Island, Toronto, Sault Ste. Marie, Detroit, and Niagara Falls 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 $6,799 to $23,495 for a vacation of 8 to 13 days. Choose any of the below 7 itineraries in September 2025 and customize it when you contact one of Adventure Life's expert Great Lakes trip planners.
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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
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
Admire the stunning views of Lake Superior
$10,300
EXPLORE

Great Lakes - Wilderness and History on vast Lake Backdrops

Toronto to Milwaukee - 13 Day Itinerary aboard Hanseatic Inspiration
  • Experience all five lakes
  • Lock adventures in Welland Canal
  • Visit Sault Ste. Marie Canal
  • Discover islands, and lighthouses
Starts / Ends:
Toronto / Milwaukee
Activities:
Hiking, Local Market Visits, Village Visits
Activity Level:
Variable
Relax on a on a 13-day cruise through the enchanting landscapes of the Great Lakes. Sail the majestic Lake Erie, conquering locks with heights rivaling Niagara Falls. Navigate Parry Sound's scenic water labyrinth and discover the captivating Thirty Thousand Islands. Witness the pristine beauty …
Cruise Details
0
Explore the picturesque shoreline of Lake Superior
$6,995
EXPLORE

Great Lakes Explorer

Milwaukee to Ontario - 8 Day Itinerary aboard Viking Great Lakes
  • Begin your journey in Milwaukee
  • Explore Mackinac Island
  • Explore shipwrecks, formations
  • Hike Killarney Park's scenic trails
  • Explore scenic vistas in Frazer Bay
  • Witness Soo Locks' wonders
  • Visit Thunder Bay's silver mine
Starts / Ends:
Milwaukee / Thunder Bay
Activities:
Hiking, Land & Sea Exploration, Small Ship Cruises
Activity Level:
Variable
Set sail on an 8-day voyage aboard the Viking Great Lakes through the Great Lakes. Begin in Milwaukee, a city with a rich history of brewing and a vibrant art scene. Explore the car-free streets of Mackinac Island. Dive into the picturesque Fathom Five National Marine Park, exploring sunken …
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
1-7 of 7 Results
TrustScore 4.9 | 318 reviews
TrustScore 4.9 of 5
total score
Based on 318 reviews on
review score
17 hours ago
I wasnt thrilled with the island choices offered on our dates but my friend suggested cruising and you have good reviews
Joyce Schiavo
review score
1 day ago
I was given all the information that I asked for and my questions were answered quickly. Very pleasant and knowledgeable agent.
Miriam Weininger
review score
3 days ago
The company representatives were totally dedicated to helping me secure my trip! I was very impressed with how courteous and knowledgeable they were!
Carey Atkins
review score
3 days ago
Friendly people who ask good questions to make sure your trip is what you want
K.Godinez
review score
3 days ago
The trip planners at Adventure Life are excellent - very knowlegable, helpful, professional and responsive.
Avi Argaman

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