computerised map

Hi all

This is a question from my dear husband...

He is wanting a to plot our travels in great detail onto a map and then squish it down the size of a computer screen.

We can get the maps off Googlemaps and plot the trip using Paint, but can't figure a way to save more than one map.

I hope this makes sense. Can anyone suggest someone we could talk to about this, or a website we could try?

Thank you!