Quote from PhanxThis sounds miserable, as no GUI client for Git I've ever seen has this functionality -- they all just "push tags". If I wanted to type crap on the command line all the time, I'd use Linux. My first several computers ran DOS, and I don't see why anyone would voluntarily go back to that for basic everyday functionality. :p
I will say that TortoiseGit (which is what everyone uses on our Windows dev boxes at work) has a 3-state checkbox for tags on pushes, as well.
Git for Windows installs MINGW (which is like Cygwin lite) as part of its install (it calls it "Git Bash"). I use ConEmu to run MINGW and do all my gitty stuff from there (Git for Windows also installs a lighter terminal replacement which is functional). I do have Tortoise installed at work, though, because an interactive Git log viewer is a million times better than anything you can do on the command line.