*** I am not an insurance expert; this is just my own experience ***
The older you are, the more time it will take to sort this out.
First, see what your credit card covers. Read carefully.
Second, see what your health coverage says about travel, specifically out-of-home-jurisdiction travel.
You only need travel insurance for what’s left over. So:
The travel part:
- Look for trip cancellation (before you go) and trip interruption (while you’re away). Make sure you understand the remedies and costs that are covered. Check your credit card: you might have some protection against surprises, or not. Last year I read the fine print and discovered that in order to insure our bought-a-year-ahead tickets, I had to have bought the insurance within seven days of buying the tickets.
The health part:
- U.S. residents, be aware that healthcare in many countries isn’t priced the way it is in the U.S. You’re not as much at risk of a $180,000 bill for what seemed like a modest treatment. It’s worth a quick check on each of the countries you’ll visit.
Check your health plan to see what’s covered when you’re out of your state/province or country. If you just turned 65 or 70, check it again. Then go buy what isn’t covered. This is another time to check your credit card. On our last trip, which lasted 14 days, I was pleased to see that my card covered us for 15 days!
- If you have chronic health conditions
- insurers lately have been fairly reasonable about conditions that might last a long time; they are mostly looking to see if your condition is stable and managed. Your premium might not go up as much as you fear
- expect a bit of a hit from lesser conditions such as asthma, which seems to be treated as if every case is a serious one. Premiums will be a tad higher, and you may be asked to fill out a more detailed application.
- Shop around. That company that was the most expensive last time may be the cheapest now. But note that wherever you start, you will probably end up with one of just a few companies. If you’re a Costco member, give their deal a look.
One-time or a year?
You can insure each trip, or buy a deal for a year. If you are sure you will be taking multiple trips in a year, the annual deal can be good. Read the limitations carefully.