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Toronto Bicycling Tours & Trips

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On these top 5 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
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
Wildlife Viewing, 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 $8,299
Save $500
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
Relax on the shores of the Great Lakes
from $8,299
Save $500
EXPLORE

5 Great Lakes + St. Lawrence Seaway: Chicago to Montreal

Chicago to Montreal - 13 Day Itinerary aboard Victory II
  • Sail all five Great Lakes
  • Visit car-free Mackinac Island
  • Tour the historic Soo Locks
  • Stand near thundering Niagara Falls
  • Visit Chicago's Millennium Park
Starts / Ends
Chicago / Saint Lawrence River
Activities
Archaeological Site Visits, Urban Exploration, Local Market Visits, Biking
Activity Level
Variable
A 13-day cruise across all five Great Lakes and the St. Lawrence Seaway, aboard Victory II. Sail from Chicago to Montreal by way of ten ports, including Mackinac Island, the Soo Locks, and Niagara Falls. A good fit for travelers drawn to North American history and lakeside cities, without the crowds of an ocean cruise.
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,499
Save $500
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
Explore the rocky shores and clear waters of Lake Superior
from $6,799
Save $500
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
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Clara T.
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