I can't add much to this since we have never insured any trips (including 2 world cruises). Knock on wood, we never would have had a claim if we had insured. Like Doug said, I guess we've been self insuring and saved $$$ through the years not insuring (we have always had Med Jet).
.....but for the first time we did insure our upcoming trip to Antarctica. It is so remote and so expensive should anything happen on or before we leave, evacuation was our particular concern.

We have worked with Steve Dasseos, the owner of http://www.tripinsurancestore.com who is fantastic, very attentive, patient and knowledgeable. Any questions you have can probably be answered on his website or a phone call.

Hopefully, we'll never need it but this go around it is giving us peace of mind.