That was actually the hardest part. I tried to install it via chocolatey, but it couldn’t convince gem that the SSL certificate supplied by the server of ruby gems is valid. I tried multiple hacks, but none of them worked.
The next thing I thought about, was to install a Linux VM, but that was quite inconvenient to always change between my real desktop and Linux just to compile.
Long story short, the final solution was on GitHub. PortableJekyll is a project you definitely should take a look at, if you plan on building a website with Jekyll on Windows. I cannot thank this man enough for creating this, it took away a lot of pain for me.
Understanding Jekyll’s DataViewModel is not really that hard, if you already know the concept. I don’t want to go into depth here, since there are tons of tutorials out there. If you want to use in conjunction with GitHub Pages, I recommend using JekyllBootstrap as a starting point. If you are looking to just get the hang of it, then the official docs are actually a valuable source of income, if you can get used to the very short but to the point documentation style.
Where the pain begins are if you want to do really fancy stuff like writing own blocks or tags. Those are used to replace Jekyll commands to HTML. They are not very thoroughly documented and finding some stuff may take a lot of searching around. But it is manageable. I have written a few plugins which you find on Github.
Overall, it was not that hard to port the site over. I would do it again. If I compare it to templating WordPress, Jekyll clearly wins. But everything does compared to the monster that is WordPress. “The Loop” is definitely harder to learn and manage than Jekyll.