How do I do trip insurance?
 

Couple items to consider:

1) Going to Barbados in September (Hurricane season)

2) Flights, which would normally be about $700 each for two, are being booked with miles

3) Hotel has a deposit of approximately $1200 USD, with a one week cancellation policy for the remaining $1200 USD balance due

What kind of trip insurance should I be looking in to (I have read about certain ones paying out only if flights are canceled or the hotel is closed - is that correct, or are there policies that pay out based on something less objective and extreme?

Also, how do any insurance policies account for frequent flier miles?

You can't "insure" for flights taken with FF miles because you won't suffer any meaningful financial loss if you cancel the flight - the miles will just be deposited back into your account - no harm, no foul!

You usually have to purchase your "Trip Insurance" within 10 to 14 days of booking your trip.

Different travel policies insure different risks. You have to read the policy terms to be sure the policy your purchase covers the risk you want to insure against.

Go to www.insuremytrip.com to compare policy terms and premiums for just about every type of policy available.

Most policies with "cancellation coverage" require that the hotel be closed or airlines not fly because of major storm or if you or immediately family member become sick or are to ill to travel - they DO NOT pay benefits if you decide on your own to cancel simply because you are unwilling to go.

There are cancel for any reason policies, but RoamsAround is absolutely correct that they must be purchased within a week or two of booking. If you have recently booked, then look at different policies. You can compare the benefits at www.insuremytrip.com.

You can buy trip insurance at any time, and there are a bewildering number of policies and conditions. The more you want, the more you pay.

Do you need insurance at all? If there is a hurricane, which is what you seem to be concerned about, would the hotel give a refund?

Your FF flight does not need insurance. ((*))

We've purchased our TI through CSA the past two years, and thankfully, have not had to use it. Here's the link if you want to check it out.

http://www.csatravelpro.com/

We've purchased insurance with Travelguard but have never had to use it. Since there are so many different polities, you have to figure out what works for you.
With Travelguard, I've purchased insurance WEEKS after booking a trip. However, those trips were booked months in advance and I certainly didn't wait till the last minute to buy the insurance.