Working at OSAF, I am surrounded by a bunch of uber-Pythonistas, I'm pretty comfortable doing most server-side or scripting tasks in Ruby, but ever since I started work there, I've been wanting to give Python a go.
So, the other night I decided to pull the trigger, and being a Web guy, playing with a Web-dev framework like Django seemed like a decent way to get started. I took a bit of time setting up the latest Django release, 0.96, on my laptop, which runs an upgraded Ubuntu Edgy with a hand-rolled Python 2.5.
I did have some issues trying to get Django talking to the database (PostgreSQL version 8.2), because of version-differences in the psycopg2 database connector. (I was trying to use an apparently unsupported beta release.)
Now I've got it happily talking to Postgres, running under Apache/mod_python, and I'm slowly working my way through the tutorial. Right now I'm playing around with models, and trying to map that mentally to what I want the end result to look like in the DB.
Django looks pretty nice. It seems fairly similar to Rails in a lot of respects so far -- and of course Python is super-clean and readable, which makes stuff very easy to follow.