I didn't manage to get a run at pyenv, pipsi or pipenv, but for virtualenvwrapper and tmux work great together.

I'm running linux at work and usually keep it alive for days, so tmux is used for session keeping and remote work. I've created a few bash scripts which run some tmux commands for setting up the layout as I want it and also execute "workon" for the specific virtualenv.

For working on a new project, I've another bash script which I run with the repo url and automatically clones it, creates the virtualenv with the same name as the project, installs dependencies and starts a new tmux sessions with two panes in first window and a second window for other stuff.

The great thing about tmux for me is it's low memory footprint so I can have 10-15 sessions running at a time, without worrying about the computer slowing down. What takes a bit too long is setting it up again upon a restart.