Travelling over a large distance in a car. Usually through multiple states, provinces, or countries.

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Transit by road through Kenya

I am planning to travel to Jinja in Uganda from Malawi. I wish to transit through Kenya spending probably max two nights in the process, possibly only one night. We can't get a Carnet for the vehicle ...
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Hartford to Montreal June 2015

Traveling from Hartford, CT to Montreal for world cup in June 2015, what is the easiest route? and what border crossing station would we use?