Seeking travel insurance advice
 

Any travel insurance savants here? I am thinking of purchasing, but I clearly don't fit the niches carved out by the companies I perused on "insuremytrip". I'm going to finish up the back half of a oneworld RTW I originally purchased over a year ago. I'm planning on taking my granddaughter, although she will be on different flights. So I will be purchasing her fare (unless my award guy comes through) as well as reserving and prepaying some hotels, rental cars, tours etc. I usually go bare, but this trip has already been postponed once due to my elderly mother's fall and hip fracture. (with minimal financial loss). But this round I'm going to prepay probably $6-8K.

Specifically:
* I have to pick up my trip at JFK and have purchased a separate ticket to get there. Would a flight delay causing a missed connection be covered?. This provision in the policies seems aimed at cruisers on a single seamless ticket--one thing to get to the next cruise stop, quite another to get to Katmandu.
*If something were to happen to my mother or another immediate family member and I cancel, will I be reimbursed at all? I'm assuming I'll lose the value of my ticket since not paid within 15 days of purchase, but what about the portion newly paid?

I deal with insurance companies more or less obliquely, and it's been my experience that their knee jerk reaction is denial. (Except, bless 'em, USAA). Am I right in the perception these policies are developed for people making a payment to a travel professional? Are there too many potential loopholes in this cobbled together trip?

One of the things I recommend you consider doing is contacting any of the companies you may be interested in using and asking these questions. I do know/understand that if some aspect of the trip is left out and uninsured, that could compromise the total coverage to some degree.

Have you checked to see if USAA offers travel insurance?

Have a good trip.

I know WorldNomads’ policies can cover both trip cancellation and missed connections but there are some restrictions (though the wording suggests that separate tickets are covered as long as they are booked with a minimum 3 hour connection time and in a way that there is no obvious risk of missed connections) and their terms differs depending on place of residence and final destination.

Call Steve at The Trip Insurance Store. He can pretty much answer any question you can come up with.

https://tripinsurancestore.com/

I am not connected to this company, nor do I know Steve, but he has helped with questions several times.

Don't call and ask questions. That is just plain silly. As you will see if and when you purchase, it is the terms of the policy which control. Nothing else.

By way of example, you already have a definitions issue. You refer to separate tickets, yet you use the word "connection". It is unlikely that this is a "connection" because it is on separate tickets. So, what you will need is some research into policies which cover no shows on separate tickets and that will take some careful reading.

As to sickness of others, again it is a matter of reading the policy language carefully before purchasing.

Whatever you do, don't rely on phone calls or what someone else tells you.

Always read your policy versus relying on someone's verbal responses. Nothing anyone can say will modify the terms of the written policy. Most of these are standard form policies and should be available to you for a review in PDF prior to binding coverage.

I'd recommend requesting the policy forms - they aren't very complicated to read. Review before purchasing. If there's something of concern in one policy, you can look for the issue in another and get a feel for whether it's one company's policy to exclude something or if it's consistent in the industry.