Unfortunately this is the the norm of most package managers these days, and I feel sorry pip can’t make the out-of-the-box experience more pleasant for you. If you got ideas how pip can improve the experience without compromising the zero-config default (which a lot of Python newcomers rely on), please definitely feel free to suggest them; we are all ears.

I would say that Python, and especially pip, is actually relatively friendly to scenarios where non-obstructed Internet is not generally available, compared to many other offerings from other programming languages (especially those without corporate backing). Devpi was already mentioned as a solution; in fact, since pip’s --index-url accepts a file:// URL, you can even simply pre-download the wheels, arrange them in the correct hierarchy (see PEP 503) inside a thumb drive, and just pass that around. The --find-links --no-index combination may also be an interesting approach for simple setups. There are a lot of things to try, before you conclude things do not work.