We're in our 50s, and have purchased our insurance through the cruise line. Most everyone says not to, but the Princess insurance and Celebrity insurance policies looked good to me. Try the website that Dave posted, it's a good one.
The way I read it is that you don't need the insurance until you are at your "not 100%" refundable" date. Before that why would you need insurance? Unless you purchased non- refundable airfare and wanted to protect that. Maybe you could take 2 policies, one just for the airfare and another for the cruise at the proper time.
Peter, for cruise line insurance, it depends on the cruise line. Some cruise lines make you purchase insurance with your deposit, some by final payment time.
As for outside insurance, you can purchase that any time you want. In many cases, if you purchase it within two weeks of making your first deposit, the insurance will cover you for cancellations due to pre-existing medical conditions. There are other coverage perks for purchasing it within the same two week period, such as supplier default. Again, this depends on the insurance company and the type of insurance you buy.
Most insurance will let you modify the policy if you want to cover the cost of airfare, or change the dates of departure or return. Of course, if you're increasing the amount of coverage to include airfare, or increasing the number of days you'll be away, there is bound to be an additional cost.
I never get the cruise line insurance. For the most part it is too limited in coverage. I look for a policy that covers medical evacuations, trip interruption, cancellation, and also has a waiver for pre-existing conditions if you buy it within X days of making the booking. It may not apply to others, but we have to look for something that will waive pre-existing health issues that might pop up before the cruise. Otherwise it would be "too bad, you knew you had this problem" and no compensation would be given. Cruise line policies don't offer this. And, as Jim said, the outside policies are usually cheaper too, in addition to offering more coverage.
Feeling stupid ! Can you explain when one would have an air transportation that would not be refundable; I am purchasing through my travel agent. Can someone just give me the thumb nail of what happens in the case of each if one was to have to cancel out without insurance. Thanks again for the great responses on our chat rooms.
Most airfare is nonrefundable. Unless you paid First or Business class, or full coach price which is designated on a ticket as "Y" class. The penalties involved for cancelling will depend at what point you cancel. If you have already made final payment it can be anywhere from the amount of your initial deposit up to the full amount of the cruise. Your Travel Agent should have gone over that information with you.