Where to go when

So I'm planning more.  You know, I've only got a year to do this.  Let's buckle down and cut the chit chat. Here's what I wanted to do at first:

But then, I started thinking about when I would be where: (months in tiny green letters)

Which presented a bit of a problem:

I think this is not only a "Dan's a wimp" problem.  I think it's logistical too.  I mean, we're talking about hard-to-spell Stan countries there.  You can't just hop on the interstate and expect to keep on trucking.  So I thought, well, what if I did it backwards?

Surprisingly, that helped a bit.  But maybe not enough:

So how about take three:

Perhaps I am on to something here!  Alas, this one has problems too:

But these seem comparatively minor. This is of course pending some serious investigation (for all I know, maybe the Pamirs are lovely in the dead of winter), but it's a start.