None of this constitutes financial advice or guidance. Just my personal take, written for myself, and I don't guarantee its accuracy. Take independent financial advice for any of your own decisions.

The Platinum Card from American Express comes with excellent travel insurance (among other things) that has served me very well over the years.

But it only covers you for trips up to 90 days.

The only way to reset the clock is to go back to your home country.

After a lot of digging around I found what I think is the next best option for when you’re away from home for longer than 90 days at a time.

After 90 days, I switched to SafetyWing.

They provide travel insurance on a rolling basis for $40 per 28 days ($73 per 28 days including the USA).

It’s designed for nomads.

You can be ordinarily resident anywhere.

I haven’t had to make any claims, but anecdotally I’ve heard of people who have and it’s been fine.