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Explore the rocky shores and clear waters of Lake Superior

Top Great Lakes Trips & Tours in May 2026

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Discover Great Lakes in May 2026 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2026 as you enjoy Urban Exploration, Archaeological Site Visits, Biking, Hiking, and Kayaking. Prices for trips in May 2026 range from $6,595 to $22,495 for a vacation of 8 to 16 days. Choose any of the below 7 itineraries in May 2026 and customize it when you contact one of Adventure Life's expert Great Lakes trip planners.
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    • Great Lakes
Explore the picturesque shoreline of Lake Superior
from $9,699
EXPLORE

Great Lakes and Thunder Bay

Chicago Roundtrip - 16 Day Itinerary aboard Victory II
  • See the Door County Maritime Museum
  • Take a horse-drawn carriage tour
  • Stroll Green Bay shoreline
  • Visit the historic Soo Locks
Starts / Ends
Chicago / Chicago
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.
Cruise Details
0
See the mighty Niagara Falls
from $6,595
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
Activities
Village Visits, Hiking, Kayaking
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 Toronto
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory I
  • Sail across Lake Michigan
  • Explore Milwaukee's Riverwalk
  • Bike Mackinac Island perimeter
  • Rock out in Cleveland
Starts / Ends
Chicago / Toronto
Activities
Local Market Visits
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.
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
  • Visit Chicago’s Art Institute
  • Sail scenic Lake Michigan
  • Discover Milwaukee city
  • Visit Niagara Falls
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.
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $7,299
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
Visit Cleveland, Ohio
from $6,799
EXPLORE

All Five Great Lakes

Toronto to Milwaukee - 11 Day Itinerary aboard Victory I
  • Visit Niagara Falls views
  • Explore Mackinac Island’s streets
  • Visit Milwaukee Art Museum
  • Visit Rock and Roll Hall of Fame
Starts / Ends
Toronto / Milwaukee
Activities
Archaeological Site Visits, Urban Exploration, Biking
Activity Level
Variable
Sail the Great Lakes from Toronto to Milwaukee on an 11-day cruise aboard Victory I. Discover Niagara Falls, explore Cleveland’s art scene, experience Detroit’s revival, and visit charming Mackinac Island. Visit iconic landmarks, lively cities, and tranquil islands while uncovering the rich heritage of North America’s Great Lakes region.
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
  • 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
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