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Explore the rocky shores and clear waters of Lake Superior

Top Great Lakes Trips & Tours in May 2027

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Discover Great Lakes in May 2027 on one of these 7 tours hand-selected by the travel experts at Adventure Life. Explore the best of during May 2027 as you enjoy Urban Exploration, Archaeological Site Visits, Biking, Citizen Science, and Fishing. Prices for trips in May 2027 range from $6,799 to $46,995 for a vacation of 8 to 15 days. Choose any of the below 7 itineraries in May 2027 and customize it when you contact one of Adventure Life's expert Great Lakes trip planners.
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See the mighty Niagara Falls
from $6,995
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
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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 $6,799
Save $6600
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 $6,799
Save $6600
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
Activities
Archaeological Site Visits
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 $7,995
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
Door Peninsula, cliffs, forests, and clear Lake Michigan waters
from $13,995
EXPLORE

Great Lakes Collection

Canada to Minnesota - 15 Day Itinerary aboard Viking Great Lakes
  • Cruise Niagara Falls
  • Explore Mackinac Island
  • Kayak Killarney’s turquoise waters
  • Enjoy Sleeping Giant hike views
Starts / Ends
Toronto / Duluth
Activities
Biking
Activity Level
Variable
Set sail on a 15-day voyage aboard a Viking Great Lakes cruise ship, starting in Toronto and exploring North America’s inland seas. Visit Niagara Falls, Detroit, Mackinac Island, and enjoy scenic hikes, vineyards, and optional excursions like helicopter rides on this enriching cultural voyage.
Cruise Details
0
Visit Portsmouth
from $7,299
Save $6600
EXPLORE

New England and Canada

Portland - Toronto - 12 Day Itinerary aboard Victory I
  • Explore Portland
  • Watch whales in Saguenay Fjords
  • Walk Old Quebec streets
  • Explore Charlottetown history
Starts / Ends
Portland / Toronto
Activities
Whale Watching
Activity Level
Variable
Experience a 12-day cruise from Portland to Toronto aboard Victory I and enjoy coastal views, local cuisine, and relaxing days at sea. This immersive journey blends Canadian culture, maritime history, and scenic waterways for a unique small-ship cruising experience.
Cruise Details
0
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