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Lake Michigan Urban Exploration Cruises

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Explore the vibrant cityscape of Lake Michigan on our 16 urban exploration city tours for 2025. Delve into the rich history and culture of this magnificent destination while admiring the architecture and engaging in small ship cruises along the Great Lakes. From the splendid colors of early autumn to the thundering Niagara Falls and charming Mackinac Island, these tours offer a relaxed adventure with activities like hiking, kayaking, and urban exploration. Discover the beauty of the Great Lakes and immerse yourself in Native American history as you sail through the heart of North America. To start planning your journey, contact one of Adventure Life's tour specialists for help creating your next seamless trip.
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    • Lake Michigan
Explore the picturesque shoreline of Lake Superior
from $9,699
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Great Lakes and Thunder Bay

Chicago Roundtrip - 16 Day Itinerary aboard Victory II
Starts / Ends
Chicago / Chicago
Activities
Biking, Urban Exploration, Archaeological Site Visits
Activity Level
Variable
Sail from Chicago round-trip on a 16-day Great Lakes and Thunder Bay cruise aboard Victory II and explore scenic ports across the Great Lakes. Cruise through Lake Michigan and Lake Superior on a journey full of natural and historic highlights.
  • See the Door County Maritime Museum
  • Take a horse-drawn carriage tour
  • Stroll Green Bay shoreline
  • Visit the historic Soo Locks
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $9,699
EXPLORE

Great Lakes and Thunder Bay

Chicago Roundtrip - 16 Day Itinerary aboard Victory II
Starts / Ends
Chicago / Chicago
Activity Level
Variable
Embark on a 16-day Great Lakes and Thunder Bay cruise aboard Victory II through Lake Michigan, Lake Superior, and Lake Huron. Visit Mackinac Island by horse-drawn carriage, explore historic Duluth and Green Bay, and witness the Soo Locks in action. Step into Canada at Thunder Bay and tour museums, national parks, and charming waterfront towns.
  • See Chicago’s stunning skyline
  • Take a horse-drawn carriage tour
  • Thunder Bay sightseeing tour
  • Visit the historic Soo Locks
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,299
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
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.
  • Discover Michigan's Upper Peninsula
  • Explore Detroit's Henry Ford Museum
  • Stroll Chicago’s Navy Pier
  • Visit Niagara Falls up close
Cruise Details
0
Visit historic locations along the shores of the Great Lakes
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
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.
  • Visit car-free Mackinac Island
  • Sail through the Soo Locks
  • Explore the Henry Ford Museum
  • Visit Escanaba's lighthouse
Cruise Details
0
Explore Toronto
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory I
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day cruise aboard Victory I at Chicago’s Navy Pier and cruise across all five Great Lakes. Explore Milwaukee’s breweries, Mackinac Island’s historic charm, the Soo Locks at Sault Ste. Marie, Detroit’s vibrant art scene, Cleveland’s Rock and Roll history, and the power of Niagara Falls.
  • Sail across Lake Michigan
  • Explore Milwaukee's Riverwalk
  • Bike Mackinac Island perimeter
  • Rock out in Cleveland
Cruise Details
0
Golden light over the Chicago skyline
from $6,799
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
Views on Mackinac Island
from $7,299
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All Five Great Lakes

Milwaukee to Toronto - 11 Day Itinerary aboard Victory I
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Sail on an 11-day cruise aboard Victory I from Milwaukee to Toronto, exploring the heart of the Great Lakes. Embrace historic cities, natural wonders, and vibrant culture while enjoying scenic sailings across Lakes Michigan, Superior, Huron, Erie, and Ontario.
  • Scenic Lake Michigan sailing
  • Visit Toledo’s Henry Ford Museum
  • Niagara Falls boat adventure
  • Mackinac Island carriage rides
Cruise Details
0
Detroit, Michigan at Dusk
from $7,299
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All Five Great Lakes

Milwaukee to Toronto - 11 Day Itinerary aboard Victory I
Starts / Ends
Chicago / Toronto
Activities
Wildlife Viewing
Activity Level
Variable
Set out from Chicago and sail the Great Lakes on an 11-day cruise aboard Victory I. Along the way, enjoy scenic sailing on Lake Michigan, Superior, Huron, and Ontario, each offering beautiful views and rich history.
  • Rock out in Cleveland
  • Visit Sault Ste. Marie
  • Niagara Falls boat adventure
  • Mackinac Island carriage rides
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 $7,299
EXPLORE

All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I
Starts / Ends
Toronto / Chicago
Activities
Local Market Visits
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.
  • Discover the diverse food scene
  • Enjoy the vibrant nightlife
  • Visit Niagara Falls
  • Explore Niagara Peninsula
Cruise Details
0
Mackinac Island, Michigan
from $10,570
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A Voyage Along the Great Lakes – with Smithsonian Journeys

Toronto - Milwaukee - 8 Day Itinerary aboard Le Champlain
Starts / Ends
Toronto / Milwaukee
Activity Level
Variable
Set sail on an 8-day cruise aboard Le Champlain to explore the breathtaking Great Lakes. Begin in vibrant Toronto, marvel at Niagara Falls, explore Manitoulin Island, traverse the Soo Locks into Lake Superior, and relive Mackinac Island’s Victorian charm before concluding in Milwaukee.
  • Explore Toronto's vibrant museums
  • Admire Niagara Falls' splendor
  • Navigate Detroit's waterways
  • Enjoy Chicago's urban elegance
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $6,799
EXPLORE

All Five Great Lakes

Toronto to Chicago - 11 Day Itinerary aboard Victory I
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.
  • See powerful Niagara Falls
  • Explore Cleveland’s rock history
  • Tour Milwaukee’s lakefront gems
  • Visit peaceful Mackinac Island
Cruise Details
0
Detroit, Michigan at Dusk
from $7,299
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
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.
  • Explore Toronto
  • Experience Niagara Falls
  • Visit Henry Ford Museum
  • Enjoy a horse-drawn carriage tour
Cruise Details
0
Stunning Niagara Falls
from $7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Montreal - Chicago - 13 Day Itinerary aboard Victory I
Starts / Ends
Montreal / Chicago
Activity Level
Variable
Embark on an unforgettable 13-day cruise from Montreal to Chicago aboard the Victory I, exploring all five Great Lakes. This voyage combines scenic sailing with onshore excursions, offering a unique blend of urban exploration and natural wonders.
  • Discover the city of Toronto
  • Visit the Henry Ford Museum
  • Visit Lake Huron
  • Savor local delicacies
Cruise Details
0
See the mighty Niagara Falls
from $6,295
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Niagara and the Great Lakes

Toronto - Milwaukee - 8 Day Itinerary aboard Viking Great Lakes
Starts / Ends
Lake Ontario / Milwaukee
Activities
Hiking, Kayaking, Village Visits
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.
  • 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
Cruise Details
0
Relax on the shores of the Great Lakes
from $6,799
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
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 all five Great Lakes
  • Visit Niagara Falls up close
  • Tour Cleveland’s museums
  • Visit Mackinac Island
Cruise Details
0
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TrustScore 4.8 | 547 reviews
TrustScore 4.8 of 5
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Based on 547 reviews on
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2 hours ago
It is always so easy planning trips with Mary Curry. And I know from experience that the follow-through will be excellent as well.
Rosemary Bell

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