Anyone sail without insurance and regret it?

My father in law went on a cruise several years ago without trip insurance and went on a Segway tour in Mexico. Someone in their group ran over his foot before the tour even officially started, breaking couple of bones. He had to come up with the money upfront before the hospital there would treat him. I don't remember the exact cost, but it was pretty steep and took a while to get it there. He barely made it back to the boat on time once he was finished at the hospital and if he wouldn't have made it, thats another huge uncovered expense to either fly home or catch up with the ship. He always buys trip insurance now. It could've been much worse than just out of pocket for a broken foot.
 
I wish people wouldn't keep saying Medicare doesn't have coverage outside the US and leave it at that, even giving Alaska cruises as an example.

It's a correct generalization, but not completely true. The best source is Medicare itself. The link is https://www.medicare.gov/Pubs/pdf/11037.pdf

There's even a section on coverage on cruise ships. So, don't shortchange yourself and automatically assume that what is usually true must be always true.
 
From https://www.medicare.gov/Pubs/pdf/11037.pdf
In most situations, Medicare won’t pay for health care or supplies you get outside the U.S. The term “outside the U.S.” means anywhere other than the 50 states of the U.S., the District of Columbia, Puerto Rico, the U.S. Virgin Islands, Guam, American Samoa, and the Northern Mariana Islands. This fact sheet explains some of the exceptions that would allow you to get coverage outside the U.S. under Original Medicare Part A (Hospital Insurance) and/or Medicare Part B (Medical Insurance).

When does Medicare cover health care services in a foreign hospital? There are 3 situations when Medicare may pay for certain types of health care services you get in a foreign hospital (a hospital outside the U.S.):
1. You’re in the U.S. when you have a medical emergency, and the foreign hospital is closer than the nearest U.S. hospital that can treat your illness or injury. Must be in the US to start with.
2. You’re traveling through Canada without unreasonable delay by the most direct route between Alaska and another state when a medical emergency occurs, and the Canadian hospital is closer than the nearest U.S. hospital that can treat your illness or injury. Medicare determines what qualifies as “without unreasonable delay” on a case-by-case basis. Only Canada, not any other nearby country.
3. You live in the U.S. and the foreign hospital is closer to your home than the nearest U.S. hospital that can treat your medical condition, regardless of whether it’s an emergency. Remember, in these situations, Medicare will pay only for the Medicare covered services you get in a foreign hospital. Again, if you are in the US. Not already outside the US.

Yes, in some instances Medicare covers some procedures "outside the US". But, mostly not.

Will Medicare pay for medically necessary health care services I get on a cruise ship? Medicare may cover medically necessary health care services you get on a cruise ship in these situations:
• The doctor is allowed under certain laws to provide medical services on the cruise ship. Not sure exactly what this means.

• The ship is in a U.S. port or no more than 6 hours away from a U.S. port when you get the services, regardless of whether it’s an emergency. Medicare doesn’t cover health care services you get when the ship is more than 6 hours away from a U.S. port. "6 hours" is that 6 hours travel by ship, or in a straight line?

Personally, it's worth the small extra cost to know I have coverage with a company that is in business to provide coverage "out of the US". No small print to wade through.
 
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I've completed 10 cruises and have a few more on the books and never purchased insurance. Only once did I almost regret not getting insurance when I fractured my clavicle in several places three days before a cruise. I couldn't schedule surgery before the cruise so I went on the cruise with a broken clavicle. Luckily I had plenty of vicodin and the cruise was a short 5-day reposition cruise.
 


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