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saskskierYeah. It seems like you are taking a lot of time to go through the prairies.
Winnipeg to Medicine Hat is around 10 hours (definitely less if you do like 120 the whole way, which you can on the Trans-Can). Put in a long day and then it's only a three hour drive to Calgary from Medicine Hat.
erikKThis should be incredibly easy to estimate yourself. Gas, hotels, food, tobacco, liquor, drugs, cost of activities (ex. riding horses) you plan to do along the way.
I would recommend trying to spend a day in the Okanagan if you can, it's real nice. Maybe even just go through Kelowna/Penticton/Princeton instead of Kamloops on the drive through.
Although for people from Ontario the Coquilhala will be a pretty impressive drive as well.
MacMahoooonDoing a 1 way vehicle rental is incredibly expensive, expect a few hundred extra in the return fees.
skiP.E.I.I'd also pick somewhere other than Winnipeg to have a rest day. It's definitely not one of Canada's finest towns.
Winnipeg has a solid art scene.
I will be doing the same trip in October, but blasting across as fast as possible sleeping in my tent. I'm curious about the cost of gas for a sub-compact on this trip.