I find my workflow goes best when sketching in photoshop and then taking that into illustrator to convert to a vector file. I usually use the pen tool for doing the vector portion rather than using Live Trace.
Inkscape is an open source (and free) vector program that has a good calligraphy tool (I set my pen options at 13 width, caps 1, mass 40, and everything else at 0) that makes drawing curves freehand pretty natural. You have to go to file > input devices to enable the pen though. It doesn’t have support for most opentype font features, so I still use Illustrator the most.
I really dont use InDesign at all since Illustrator can handle fonts pretty well.