Depends on your skill / background. Do you have a programming background?
Not really. I am familiar with xhmtl and css. I also quite educated in math, if that counts.
I would recommend you get a book, read some blogs, write some code for a few weeks and see if it is making sense. With Rails being a framework I think it definitely gives you the best chance to pull this off.
This is a FAQ. With the success of Rails theres been a lot of writers jumping on the bandwagon. A good rule of thumb is to choose authors who are active members of the Ruby or Rails community : David Thomas, Chad Fowler, David A Black, Obie Fernadez etc. So I recommend ADWRR, The Rails Way, Rails Recipes, Ruby For Rails
Ok. So I'm going to start of with the Pragmatic Programmers guide, that has been settled.
What do you guys think of this book: RailsSpace: Building a Social Networking Website with Ruby on Rails?
No doubt "Agile Web Development with Rails" from the Pragmatic programmers. The peepcode/screencasts mentioned by Mark above will be of great help for amateurs as well as professionals.
Max, if you are new to programming in general, I would definitely recommend that you also get a good book on Ruby. A lot of the problems you will encounter, are going to be more Ruby related than Rails related. I'm not saying you should learn all of Ruby first and then study Rails. On the contrary, the best way to learn programming is to dive in and use it straight away. But it's important to realize that you are learning two things at the same time: The programming language Ruby, and the framework Rails.
For learning Ruby, I'd recommend "Programming Ruby":http://pragprog.com/titles/ruby/programming-ruby as your first book.
I've been playing with rails and Radiant CMS for a bit now and find that I need more in depth learning. I've gotten the 3rd edition of agile web development together with the Rails Way book. I've installed Radiant CMS on my website www.jasperkooij.com so I'm doing the depot project on my local machine using Bitnami Rubystack together with Netbeans and I'm developing a new website using Radiant. I tend to learn it more in a useful way since I have to figure things out that aren't in the books. Following the examples will always work but I learn better when it doesn't work and then figure out why.
I've used aptana before but I favor netbeans since there is better error checking ad it opens the files that are generated immediately after.
If anyone cares to join me in my learning trip of "100 days of Ruby on Rails and Radiant CMS", let me know