He could be intimidated by your natural talent and desire to put together those types of events, and doesn't think that he can match the way you do it. So he is comfortable doing what he can do, such as your recent date.
Another factor is that he is, as you said, a simple guy. He is what he is. Guys don't take hints well, so you might need to be a bit sneakier. Maybe one of your female friends could let him know sometime that "You know, I thought I'd let you know that the other day Tomato told me that she would just love to have a surprise getaway weekend in Sausalito." If he follows through, don't blow his cover. Just enjoy that he did it for you and even though it might not be a genuine surprise, it was something.
Whether you bring it up or not is up to you, but if you do, don't do it now. Wait until it won't be obvious your disappointment is tied to the evening he just planned. Because if he feels that you were disappointed in the evening that he obviously went outside his comfort zone to plan, he's not going to feel very good about himself.