This is quite a radical change for me. I've been hosting websites for years using application servers even if the website only needed simple header/footer/gutter wrapping. It took a bit of work, but here's how I took the jump from dynamic sites to static.
Every website I've built has required some form of standard navigation decoration. I've used sitemesh for nearly all of my projects, and it is by far the best solution out there for dynamic page decoration. Obviously, without an application server, something needed to change, and luckily I ran across a tool called staticmesh. Staticmesh is built ontop of sitemesh for offline website generation. So, instead of dynamically decorating pages at request time, I use site mesh to decorate pages at "build time". I whipped up a quick little Maven2 plugin in about 10 minutes, and just like that, I had a solution for 90% of my application server needs. I can share my Maven2 plugin if anyone is interested...