Start with Canada. Then guess its northernmost neighbour (by point on land). Then guess the northernmost neighbor of that country, etc... When you reach a dead end, go back and choose the next northernmost-neighbor. Finally, when you're done with continents continue onto the islands.
Overseas territories don't count, but overseas regions do
Yes: France/Brazil, Morocco/Spain
No: France/Netherlands, UK/Spain
Dubious land borders not considered: Sri Lanka/India, Qatar/UAE