Travel insurance

There are dozens of posts on this forum about travel insurance. Here's a quick search I did that filters it down to the last two years:
https://search.ricksteves.com/?button=&date_range=2y&filter=Travel+Forum&query=travel+insurance&utf8=%E2%9C%93

I would go through those and look at the responses, then if you have any questions, you can always come back and ask. But FWIW, I have never heard of a policy that rejects people over 49.

Two good places to comparison shop, as well as learn more about travel insurance, are InsureMyTrip and Squaremouth. I've never heard of a cutoff at age 50 (or any age), but premiums will be higher the older the traveler is, because medical coverage is an important part of any policy worth buying.

If you have USAA, look on their website for trip insurance. That is who we have bought through and they have been good to work with.

Some credit cards offer a travel insurance program.
Be sure to buy travel medical AND trip cancellation insurance.

Be sure to consider Medical Emergency Transportation or Evacuation in case you’re injured or become ill or, God forbid, die. It’s very expensive and if you don’t want to pay for it out of your pocket, consider sharing the risk with the insurance company.

Medical insurance, trip interruption or cancellation and emergency medical transportation or evacuation are important to evaluate for your own situation.

Some policies will only cover trips of 30 (not 31) days, which could be limiting your search results.

With regard to medical evacuation insurance, the devil is always in the details. Many policies will only transport you to the nearest facility that can treat you. There is at least one company (maybe more) that will transport you back home if you are admitted to a hospital overseas. Check out MedJet Assist in Birmingham AL. They have a variety of plans you might want to consider. It is not travel insurance nor medical insurance -- just med. evac. insurance.

I always book my medical coverage and evacuation with American Express when we go overseas. I can get $100,000 coverage with medical evacuation for about $60 for my wife and self.

As for trip cancellation coverage, I rare buy that type of coverage unless we take a tour or cruise, then I might purchase that coverage. This coverage is way more expensive than just the medical.

My wife and I are old seniors. She is 68 and I'm 67.
We are using Travel Guard for a trip to Israel nest year, our old ages were never a factor
when they signed us up.

I use GeoTrekker multi trip because it was recommended by friends traveling with OAT. Haven't had a claim, YAY, but it seems to cover most of the bases others discussed. And I'm over 65. It covers up to 70 days per trip. I did call my Medicare provider to discuss what they would cover overseas, basically hospital, doctors & medications, but not the extra time in hotels, your travel companion's expenses, etc....