Not currently possible, sorry, although it's a good idea!
Some initial thoughts on how this could be implemented:
Current map data is stored as distinct tiles (either squares or hexagons)
Cluster tiles into groups, by iterating over all tiles, and for each tile, if it shares two or more vertices with an existing group, add it to that group; otherwise, add it to a new group
Grouping should also be sensitive to color (i.e. only vertices of the same "color" can be in a group)
We may then have to run a de-duplication step to eliminate any identical (i.e. stacked on top of each other) tiles
For each group, determine the set of border vertices. For squares, these would be vertices which belong to three or fewer tiles. For hexagons, these would be vertices which belong to two or fewer tiles
For each set of border vertices, draw the border line through that set of vertices
This would center the line on the border, i.e., if the border was 5 px wide, 2.5px would render outside the group, and 2.5px render inside the group. This may not be good enough. Consider instead some method of determining which side is "inside" and which side is "outside" (e.g. winding order algorithm) and using this to offset the border to ensure it stays within the bounds of the group
FoundryVTT focus a lot on battle maps, but this helps us in our world maps that we are higher level and running armies.
One problem we run into is that if the world map uses deeper or richer colors, the highlight is not so obvious.
Is there a way to add a darker color border around political areas?