Django has a lot going for it in terms of simplicity but it lacks most of Rails' advanced features and timesavers. In my experience it sits somewhere between Sinatra and Rails
I use Pipenv currently, but only because it's the best of a bad lot and would jump in a heartbeat if a serious competitor came along. It has its own set of problems (slow, young and idiosyncratic) but offers me at least two things its predecessor didn't: separation of production/dev dependencies and seamless integration with different versions of Python, both of which have been available in Ruby since I started programming in it.
This is a perfect exemplifies my experience with both languages: I have found while Python might be better at a lot of things, the user experience is invariably superior with Ruby efforts and I wish the Python community would put more effort into this area.