We had worked together for years at this small company. He moved to northern CA and still worked for us but was the only remote employee. He was a founder though so no one was going to question it. Anyway, after the company sold, I got a remote manager job at a SV company (not FAANG) and lured him to join me. Once his daughter graduated college, he moved to a house he had bought in Spain and worked from there for most of the year. Our team was mainly East Coast and Europe so it worked better having him in Spain anyway.
He spends roughly half the year in Spain. He owns a small cottage on a lake in NH and will spend a couple months of the summer there. His daughter lives in DC so he will spend a month or so with her. His wife's family lives in Atlanta area so he will spend a month or so with them. Before Covid, he also listed his Spain house on a house sharing site and used that to spend a month here and there in lots of cool places like Paris, Nice, Croatia and the Canary Islands among others.
It obviously helped that I was his manager and knew that this nomadic life would not impact his work but other than that I think it is a model for what a lot of people would like to do, especially in the back part of their careers.