On the first cruise we took 5 years ago we were not going to purchase travel insurance. Why spend the extra money? Our parents were in good health and our kids would be with us on the cruise.
We opted to purchase insurance at the time we made our final payment for the cruise (about 60 days prior) because the travel agent told us that if one of our kids fell on the ship and broke a bone and had to be airlifted it would be 25K. That alone convinced us...
Just to show how things can change...
In that 60 days after purchasing the insurance for the cruise, my father, who was in good health, died unexpectedly. My mother, who was in excellent health, ended up in the emergency room near death, unbeknownst to us, as we boarded the ship on the day of the cruise. We were on the ship for about an hour when the phone call came that they didn't expect her to survive. It was totally unexpected! We had to leave the ship immediately and the insurance covered the cruise and all transportation, including last minute airfare during the Christmas season (imagine the cost!) It was well worth it and convinced us to never cruise without insurance!
Life is unpredictable!