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Top Toronto Trips & Tours in September 2025

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Discover Toronto in September 2025 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of Toronto, Sault Ste. Marie, Mackinac Island, Cleveland, and Lake Huron 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 $50,995 for a vacation of 11 to 16 days. Choose any of the below 7 itineraries in September 2025 and customize it when you contact one of Adventure Life's expert Toronto trip planners.
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A polar bear wanders onto an iceberg in Greenland
$24,795
EXPLORE

Northwest Passage

Calgary - Toronto - 16 Day Itinerary aboard Greg Mortimer
  • Experience Qeqertarsuaq
  • Visit Prince Leopold Island
  • Discover Ilulissat
  • Explore Sisimiut
Starts / Ends:
Calgary / Toronto
Activities:
Helicopter Tours, Hiking, Small Ship Cruises, Wildlife Viewing
Activity Level:
Variable
Embark on a 16-day expedition cruise aboard the Greg Mortimer. Explore a segment of the legendary Northwest Passage, a historic and captivating route cherished by early explorers like Franklin, Amundsen, and Larsen. Visit the resting places of these pioneers and discover Canada's High Arctic …
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
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
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
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
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