How do I make a calendar?

I’m looking for some software recommendations to design a yearly calendar—specifically one where the entire year is laid out on a single A3 sheet. It needs to be in English, complete with all our local American holidays and observances.
Here is what I currently have installed: Microsoft Office 2003 and 2010, Adobe Illustrator, and Photoshop...
Is it actually possible to pull this off using these specific tools, and if so, what would be the best way to go about it?

You don't even need to bother with extra software, everything is right here ready to go.
Just pick your settings and knock out the PDF...

The real issue here—if I'm being honest—is that I need to be able to insert an image right at the very beginning

How to embed an image into a PDF

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