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Toronto Bicycling Tours & Trips

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On these top 7 Toronto bicycling tours, you'll stroll down meandering roads, trails, and bike paths as you take in the Toronto scenery.  A guided small group or private guided cycling tour of Toronto may include bike rides near popular cycling destinations like . Our Toronto bicycling trips start at $6,799 for a 11 days tour and may include leisure cruising, mountain biking, or road biking. Tell us about your ideal Toronto cycling adventure and one of our Toronto travel experts will help you build the ideal bicycling vacation.
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    • Toronto
Explore Toronto
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory I
  • Explore Mackinac Island by bike
  • Lake Huron sailing
  • Learn Detroit creative revival
  • Experience Niagara Falls
Starts / Ends
Chicago / Toronto
Activities
Local Market Visits
Activity Level
Variable
Sail the Great Lakes on an 11-day cruise aboard Victory I, exploring Chicago, Milwaukee, Mackinac Island, Detroit, Cleveland, Niagara Falls, and Toronto. You experience historic locks, island cycling, cultural cities, and scenic lake passages across interconnected inland seas.
Cruise Details
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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, Wildlife Viewing, Urban Exploration, Hiking, Village Visits, Kayaking, Citizen Science, Wine Tasting, Fishing
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
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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
  • Niagara Falls visit
  • See Cleveland Rock Hal
  • Observe Soo Locks transit
  • Mackinac Island cycling
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.
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,499
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
  • Lake Michigan crossing
  • Stroll Milwaukee Riverwalk
  • Visit Cleveland Rock Hall
  • Niagara Falls visit
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.
Cruise Details
0
Mackinac Island, Michigan
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Explore Navy Pier and city skyline
  • Visit Milwaukee craft breweries
  • Lake Michigan sailing
  • Enjoy Escanaba waterfront views
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day Great Lakes cruise aboard Victory II from Chicago to Toronto. Explore Detroit, Cleveland, Mackinac Island, Niagara Falls, and Milwaukee. Sail Lake Michigan, Huron, and Superior. Participate in cultural programs, enjoy scenic decks, and witness engineering marvels at the Soo Locks.
Cruise Details
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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
  • 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
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
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