If you are the creator of DEMO.Detail, you could add __repr__ and __str__ methods:
class Detail:
    def __str__(self):
        return "string shown to users (on str and print)"
    def __repr__(self):
        return "string shown to developers (at REPL)"
This will cause your object to function this way:
>>> d = Detail()
>>> d
string shown to developers (at REPL)
>>> print(d)
string shown to users (on str and print)
In your case I assume you'll want to call dict(self) inside __str__.
If you do not control the object, you could setup a recursive printing function that checks whether the object is of a known container type (list, tuple, dict, set) and recursively calls iterates through these types, printing all of your custom types as appropriate.
There should be a way to override pprint with a custom PrettyPrinter. I've never done this though.
Lastly, you could also make a custom JSONEncoder that understands your custom types. This wouldn't be a good solution unless you actually need a JSON format.