If you want to migrate more slowly you might consider getting into Groovy. It's very very Ruby like, but maintains compatibility with most Java syntax. You can

If you want to migrate more slowly you might consider getting into Groovy. It's very very Ruby like, but maintains compatibility with most Java syntax. You can start by learning Groovy and applying it in the Struts world that you know and love. Then you can try out Grails and get a feel for a Rails-like framework. Then you if you like it you can jump over to Rails and you'll find a lot of what you learned from Groovy / Grails is very conceptually similar. By doing it this way you can widen your knowledge without ever having to make the big jump that can be so disorienting, and all of the above technologies are worthy of learning in their own right.