I turned 60 this year. While I have done a few longish voyages in the past, my ultimate cruising plans are on hold for another 5 years. The reason for that is that whilst we have have some cash reserves it will be nice to have the annuities and pensions kick in as well (my wife's too). In short, our planning for a financially sorted old age weren't as good as we thought so some compromise is required.
That said, I will spend the next 5 years sailing locally, maybe a trip or two to Fiji or Vanuatu and taking care of the boat with some upgrades and good quality maintenance. The local trips will serve to shake out any remaining bugs.
We will then set sail for a circumnavigation and will keep going until we're not enjoying it anymore. I am blessed with great health and long may it endure. My missus on the other hand is not all that great with some long standing health issues which whilst not life-threatening are a continual nuisance. But history has proven that she suffers much less from her hereditry ailments when we're at sea.
Our current vision is 5 years at sea from age 65 and we'll see whether we stay that long and if so, then we'll see how much further.
So at 55 you're still in a strong age position. I have met and spoken to many sailors over time that are way older than me and still having a trouble-free time at sea. It seems from these discussions that when things on the boat become physically unmanageable (too big, too heavy), it's time to go home. Mostly it's not about health but about physical strength.
Sailing without my wife though would be a daunting prospect - I have no real further comment on that subject.
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"Two possibilities exist: Either we are alone in the Universe or we are not. Both are equally terrifying."
Arthur C. Clarke