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Top Milwaukee Cruises & Trips

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Explore these 6 top Milwaukee cruises for 2023 and 2024. Some of the most popular activities on our Milwaukee trips include cruises, small ship cruises, urban exploration, kayaking, and hiking. Discover Milwaukee with your expert local English-speaking guides who will show you the hot spots and the off-the-beaten-path hidden gems. We work with only the best small ships that carry under 500 fortunate guests, and we can give you unbiased advice to match you with the perfect ship and perfect cruise for your next vacation. Our Milwaukee cruises start from $5,989 for cruises of 8 to 15 days. Contact one of Adventure Life's Milwaukee cruise specialists for help planning a seamless trip.
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Mackinac Island, Michigan
$6,980
EXPLORE

A Voyage Along the Great Lakes – with Smithsonian Journeys

Milwaukee - Toronto - 8 Day Itinerary aboard Le Champlain
  • Explore the five Great Lakes
  • Visit charming Mackinac Island
  • Learn about Native American history
  • Visit the Niagara Falls
  • Cruise Biosphere Reserve of Georgia
Starts / Ends:
Milwaukee / Toronto
Activities:
Hiking, Kayaking, Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Set sail aboardLeChamplainfor an8-day cruiseto discoverthe Great Lakesamidst the splendid colors of autumn.Depart fromMilwaukee, Wisconsin, the United States’ “brew city,” and begin your voyage by sailing the length ofLake Michigan, a veritable inland sea, following in the …
Cruise Details
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Stunning Niagara Falls
$8,369
EXPLORE

Milwaukee to Montreal

15 Day Itinerary aboard Ocean Navigator
  • Discover Chicago
  • Visit the beautiful Lake Michigan
  • Cruise through Georgian Bay
  • Admire the Niagara Falls
Starts / Ends:
Milwaukee / Montreal
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Explore the midwest on this 15-day Milwaukee to Montréal Cruise aboard Ocean Navigator. As you sail across the diverse cerulean hues of Lake Michigan, look out for sand dunes that blend into the horizon as the sun shines on the deck. You will also visit the charming and unique Mackinac …
Cruise Details
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Beautiful Toronto Skyline
$9,160
EXPLORE

Expedition in the heart of the American Great Lakes

Milwaukee - Toronto - 11 Day Itinerary aboard Le Champlain
  • Discover Lakes of North America
  • Enjoy exceptional sailing
  • See the Niagara Falls
  • Visit Mackinac Island
Starts / Ends:
Milwaukee / Toronto
Activities:
Hiking, Kayaking, Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Set sail aboardLe Champlainfor a 11-dayexpedition cruiseto explore the natural and cultural treasures oftheGreat Lakes of North America, surrounded by flamboyant nature painted in the colors of the Indian summer. Departing fromMilwaukee, you will sail onLake Michigan, a veritable inland sea, and …
Cruise Details
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Downtown Cleveland with River Bridge
$5,989
EXPLORE

Toronto to Chicago

11 Day Itinerary aboard Ocean Navigator
  • Explore the cultures of Chicago
  • Enjoy views of Lake Michigan
  • Cruise through Georgian Bay
  • Admire the thundering Niagara Falls
Starts / Ends:
Toronto / Milwaukee
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Discover the highlights of the Great Lakes on this 11-day cruise from Toronto, Ontario to Chicago, Illinois. Explore favorite ports of Lakes Michigan, Huron, Erie, and Ontario, and immerse yourself in the natural beauty of the lakes. Discover the history of industry and its role in the making of …
Cruise Details
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Mackinac Island, Michigan
$8,930
EXPLORE

Expedition between Lake Michigan & Lake Superior

Milwaukee - Thunder Bay - 11 Day Itinerary aboard Le Champlain
  • Discover cultural riches
  • Enjoy hiking and kayaking
  • Sail on three of five Great Lakes
  • Learn about the culture
Starts / Ends:
Milwaukee / Thunder Bay
Activities:
Biking, Hiking, Kayaking
Activity Level:
Relaxed
AboardLeChamplainonan all-new 11-day expedition cruisediscovering Lake Superior, an exceptional exploration amidst flamboyant nature and the cultural riches of the Indigenous communities.Discover the natural and cultural treasures between Lake Michigan and Lake Superior on a brand-new excursion …
Cruise Details
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Stroll through historic Chicago
$8,369
EXPLORE

Montreal to Milwaukee

15 Day Itinerary aboard Ocean Navigator
  • Visit Mount Royal
  • Visit world-class Cleveland Museum
  • Explore St. Lawrence Market
  • Enjoy the Niagara Falls
Starts / Ends:
Montreal / Milwaukee
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Take a 15-day cruise from Montreal to Milwaukee on the Ocean Navigator to explore the Midwest. Look out for sand dunes that fade into the horizon as you cruise through the many cerulean hues of Lake Michigan while the sun shines on the deck. A popular vacation spot for people looking to get away …
Cruise Details
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