Draw text into a temporary blank image, rotate that, then paste that onto the original image. You could wrap up the steps in a function. Good luck figuring out the exact coordinates to use - my cold-fogged brain isn't up to it right now.
This demo writes yellow text on a slant over an image:
# Demo to add rotated text to an image using PIL
import Image
import ImageFont, ImageDraw, ImageOps
im=Image.open("stormy100.jpg")
f = ImageFont.load_default()
txt=Image.new('L', (500,50))
d = ImageDraw.Draw(txt)
d.text( (0, 0), "Someplace Near Boulder", font=f, fill=255)
w=txt.rotate(17.5, expand=1)
im.paste( ImageOps.colorize(w, (0,0,0), (255,255,84)), (242,60), w)
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