Hi -
The Vista "30 day trial" is offered to everyone via using a full retail version of Vista to install and as you said - no activation. Since no activation/ validation there is nothing to upgrade from.
You cannot upgrade from licensed copy of XP Pro (OEM or retail) to non-activated Vista then to a to-be activated Windows 7 as the Vista trial is "non-genuine".
I would highly suggest that you bite the bullet and clean install Windows 7. The installed apps on your XP system now may have boot or kernel mode drivers that are OLD and would very likely conflict with the new 2009 Windows 7 drivers which could possibly end up in your having to seek additional assistance for a BSOD epidemic.
Regards. . .
jcgriff2