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I have Dear Esther in my library, but I'm ashamed to say that I've never played it...I suppose I should get on that!
You can definitely do it in one sitting. It's more a story than a game - it has immensely beautiful landscapes and scenes, and a great story and dialogue, but the interactivity is rather minimal, save from roaming around. I'd say it would pair great with a glass or two of red wine, or something greener if you swing that way.