One (fairly minor) real world case where the syntax makes a difference is in web templates: you can use Ruby pretty much straight up to do templating, but Python requires more hoops and hacking, due in part to the whitespace issue. I like the fact that Ruby is flexible enough to be used as-is for templates as well as other code. BTW, it also needs to be said that that is the only place I've ever noticed the whitespace issue being any kind of problem: it's not the big deal that some python detractors make it out to be.
In short: if you're happy with Python...great! Keep using it, you made a good choice. If you want to learn another language, pick something a bit further from it... say, Erlang, Tcl, Java, or C, depending on what your needs are.