CruiseWorld 2014 and the Multi Modal Adventure

I've just started thinking about getting ready to prepare to pack for my trip. (It is two weeks away, after all).

Here's the thing I maybe didn't think through - temperatures in November.  I pride myself on packing light, and especially on Amtrak with daylong layovers, I really only want to take one bag.  I need "business casual" for Fort Lauderdale, and maybe dress up a little for Friday when I am up in the spotlight. 

But I need comfy casual for the trip home.  Okay, so far.  I can do that.  But here's the rub:
It's going to be 80 degrees in Fort Lauderdale, and probably 60 in D.C. and *maybe* 50 in Chicago, with a definite possibility of much lower temps and even snow on November 10th.  Which would argue for a fairly warm wardrobe, since I plan to leave the confines of the stations.

And I remember maybe the coldest I ever was was getting off the Southwest Chief for a quick break in Dodge City, KS back in 2007.  The train hits the station at 5am or so, and I felt like stretching my legs.  Just as a few of us stepped off, the train started moving.  It only went 1/4 mile or so down the platform, but it was 4 degrees and WINDY.  In the light jacket I had packed for a trip that was mostly spent in San Antonio, I thought I was going to die.  I mean, I am a confirmed desert rat, and anything under 70 I am prone to hypothermia.

So, now I am trying to figure out how to look good in Florida and not freeze to death in Chicago, and do it all in one duffel bag...

I'll let you know how it turns out. Or not.