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Do I know people who have never told their bosses? Yes
This one is a tough one to answer because it depends on a couple of things. First and foremost, it depends on the actual HR policy for remote work that your specific position has. I highly recommend this as a starting point for not only if you need to tell your boss, but for where you can work from. For example, I am limited to my home country (USA) minus 3 states. If the policy for your position does not require you to share where you are working from, then it is a personal decision.
I, of course, have to add a disclaimer, that I am not qualified to tell you if you need to tell your boss that you are doing van life. The above has just been my experience personally, and based on my conversations with others in the space.
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