Something like a waterfront boardwalk that curves around a bay or similar can be a great place to play around and better understand the depth of field and out of focus blurring qualities of your lenses. (Bonus points to the site if it happens to have lights as well so that you can study how point light sources are distorted and changed as they go out of focus.) While reading and math are good starting points to learn and get your head wrapped around things, eventually you are going to want to sit down in the real word and take a look at what is actually happening in the photos taken with the lens and how out of focus elements are rendered. Set your camera down on a tripod if possible, and then slowly work your way through the scene changing your focus a little bit with each shot.
Assuming you're working with digital and not film, then it is rather trivial to sit there and take hundreds of photos in short order with a slight nudge of your lens's focus ring while the auto focus is turned off. Make sure your exposure is decent, then run through the same scene with roughly evenly spaced focus differences all the way from one end of the lens's focus range to the other. Take the results home, load them up and spend time studying them on a large screen. (As a bonus, you also get to study how much 'focus breathing' your lens does, which is where a lens may change focal length based on how near/far it is focused.)
A key factor (for anyone really new who might be reading this thread) to remember when getting your head around optics and depth of field is that there is not really a volume of space that is 'in focus', and one that is 'out of focus' (or two if you account for in front/behind the in focus), but rather a thin plane that is 'in focus', and a long gradient running toward you and away from that plane of "Slightly less in focus".
If you had a mathematically perfect lens mounted to a mathematically perfect sensor that allowed infinite resolution, then there would be a single thin plane somewhere within the scene where any point of light would fall as a perfectly focused point of light on the sensor. Even just a billionth of a micron forward or back and the point of light would be distorted and 'out of focus', and the farther from this plane the point in the scene is, the more distorted the point becomes on the sensor.
The "Depth of field" concept in photography works because our lenses and sensors aren't mathematically perfect, and we're not looking at the information on an accuracy scale anywhere close to that. The error of a few microns becomes too small to tell apart from the 'true' in focus point. "Depth of field" calculators are more about "Reasonably in focus" vs "the error is becoming visible", but the point at which the error "becomes visible" is rather fuzzy and relies on your final print. (Pun only vaguely intended.)
As far as artistic use of bokeh and how far behind the subject you need the background to be for it to look nice? Well, that depends on the nature of the background - what kind of highlights and the shape of the lighting you have in the scene - and the lens. "The more the better" is often a decent rule of thumb, but as in all things photographic "It depends" comes into play. Separation of at least half the camera to subject distance is probably not a terrible place to start.
And don't forget: A boring background without texture/contrast is probably going to give you boring looking out of focus elements in an image.
Another important thing to remember: You do not need the focus plane of the image to fall perfectly on the primary subject to have the subject in focus... With care you can focus in front of the subject while keeping them within an 'acceptable range of focus', and let the farther background be more so out of focus than it otherwise would have. It does however mean that you will limit the enlargement you can make while still hiding the focus error in the subject.
If you are happy with the option of post processing the shot, and aren't restricted from using editing to get your final result, then you also can potentially use a workflow that involves blending multiple exposures. One of my friends often does shots where they will use rapid burst fire while pulling focus back from their subject. (Something which takes some skill and practice with to maintain reasonable sharpness and not introduce excessive motion blur or misalignment.) They will then go back through all the photos from the burst of a given 'shot', and take the first photo with the sharpest subject and flip through them till they have the focus distance that gave the best background, then blend the two in Photoshop.
- Enlarging the in-focus-subject shot by a slight amount can make it easier to hide the out-of-focus-subject behind it.
Canon EOS 7D | EF 28 f/1.8 | EF 85 f/1.8 | EF 70-200 f/4L | EF-S 17-55 | Sigma 150-500
Flickr: Real-Luckless