European road trip - Visiting all contiguous EU countries.

[julian427]

I'm planning to drive to all contiguous EU countries this summer, as a big road trip.

I'm going to make a small excursion from Estonia into Russia to "Bag" Finland, and then return the same way, and carry on through Latvia etc.
I know driving in Russia has a few issues (Insurance, Licence, car docs etc).

Can anyone recommend some mapping software to make a file I can make a single file that can be downloaded to my sat nav?

Can anyone recommend any "shortcuts" to maximise country count and minimise mileage?

Having to drive through Spain and back to get Portugal is a bit of a pain.....
The list of countries (and route so far) is as follows :-
France, Spain, Portugal, Italy, Austria, Slovenia, Croatia, Hungary, Bulgaria , Romania, Greece, Bulgaria, Hungary, Slovakia, Czech Republic, Poland, Lithuania, Latvia, Estonia, (Detour into Russia), Finland, Estonia, Latvia, Lithuania, Poland, Germany, (Denmark, by road), Sweden, (Denmark), Germany, Netherlands, Belgium and finally Luxembourg.
Any thoughts about the merits of going Estonia, Russia, Finland, Sweden, Denmark, Germany, rather than the route above?

Thanks in advance.