I am a reformed user of Java for everything and I would like to recommend Ruby on Rails. I don't think Ruby is the ideal solution for all problems (nor was Java a terrible choice that should now be shunned). I just think that each one has its strengths and Rails is definitely stronger for web apps.
Rather than just state that as an opinion, let me give a variety of reasons I think that:
1) Structured directories for development (each thing like the models/view/controllers, unit tests, third party plugins, CSS, JavaScript, etc., etc.) has its place in the directory structure. That makes it easier for you to learn the system, it makes it easier for Rails to know what things are without your having to configure them (no plethora of XML config files), and it makes it easier for you to understand other Rails code when you look at it. Think about the last Java code you downloaded from someone, where was everything? If they didn't have an Ant script did you even have a starting place?
2) Realism. By realism I mean a realistic view of what real web development is. It is iterative, databases change, code changes, and you have multiple development environments you regularly work within (for example, development, test, and production). Rails accommodates that from minute one. There are separate configurations for your different environments as well as database migrations to allow you to move your data forward just like your code.
3) Third party support. When I was struggling to build an older version of one of my sites a while back under Java, I kept being stymied by a lack of code I could embed to do basic stuff like giving me tagging for my objects. I don't want to build that code, 500 people have built it before me, let me just get one and use it. But it just wasn't available. Nor was there plugin code for voting, rating things, authentication (and don't start with me about crap like JAAS, that's complete overkill for 80% of all sites), etc.
4) Opinion. I love that the authors made choices and had opinions. Java is all about having 40 options for a MVC framework and 10 more for a ORM solution. Rails is about them having made one good choice for both of them and you've got an excellent starting point. If at some point the site you build grows big enough to require a different solution or you just don't like the stock one, then you can replace it but in the meantime it's a complete solution for all of your needs and it's ready to go five seconds after you type "rails ".
I could go on but at this point it's starting to be gushing. I really encourage you to look at the material at the Ruby on Rails site, PeepCode.com, and RailsCasts.com. They will give you an idea of the tons of great tutorial info available on video and that's ignoring the multitude of books and blog material out there as well.
P.S. I forgot to mention it, but JRuby is a popular solution for running Ruby on Rails web apps and then you can leverage any existing knowledge you might have about Java servers like Glassfish, etc.