If you are a C++ programmer, Java is going to feel a hell of a lot more comfortable to you than Javascript (jQuery, whatever). There are a million books for "Java for C++ Programmers," I'd suggest reading one. Keep in mind that Java is very different from C++, but the syntax should feel pretty familiar.
There are tons of advantages to using GWT to write your Javascript. A major one is the incredible debug-ability: you can insert breakpoints in your Java code and when the browser reaches those, you can inspect variables as if you were programming in a real language. The toolkit will also optimize and minify your Javascript code, easy-to-use support for internationalization, extremely advanced cross browser compatibility with basically no effort on the part of the developer...the list is long.
Ultimately, though, GWT and pure HTML complement each other. The biggest problem with making a whole site in GWT is that you get basically no search-engine optimization since all the code is Javascript and web crawlers don't do Javascript. So create the "classic" parts of your site in HTML and throw in some neat Javascript things and save GWT for the "web application" part. My biggest problem with GWT is that it really likes to consume your entire application, but this can be avoided easily enough.
Oh, and I forgot my favorite: image bundling. Basically, it allows you to put a collection of images together in an interface (Java interface ~= C++ class with only pure virtual functions), GWT puts all those together into a single image for downloading purposes and the framework on the client deconstructs those images for presentation. This reduces the number of HTTP connections required by a ridiculous amount, which is an easy way to decrease load time.