Calgary to Regina Regina to Winnepeg Winnipeg to Thunder Bay Thunder Bay to Iroquois Falls, Ontario Iroquois Falls, Montreal, Quebec Take 1 case of water per person. Please be safe. Use Hotwire.com to make hotel reservations while traveling. I gave you the cities to stay in on your journey as to how I would drive. 500 miles = 8 hours. Not sure how that works in Kilometers. It will be a lovely drive. When I drive a route like this I pack nuts for snacks. I don't eat sugar or carbs until I am at the hotel. I recommend leaving each day at 4am. Drive til early afternoon and rest.