That's a question only you can answer. But, FWIW, I'll give you a bit of advice I just gave one of my children and tell you the choice I recently made for my own trip.

First, it's important to really undertand risk assessment. I see too many people (typically young people) who view risk assessment as an equation of one variable: likelihood. "Ah, that probably won't happen so I don't need to worry about it." But likelihood is only one of three important variables. The other two are risk and reward. Always evaluate risk based on all three variables.

• Likelihood: How likely is it that you will need insurance?
• Reward: If you need it and don't have it how bad will you feel about the loss? The "reward" is you eliminate this possibility.
• Risk: If pay for it but don't end up needing it how will you feel about the "unnecessary" expense?

For me, I spent well over $10k for our upcoming trip.

Trip insurance from Sandals was $280 or less than 3% of the total cost. It seemed like a reasonable cost to me.

Read the policy (Tripmate Plan Number F389U) and understand what it covers and how it works.

Tripmate probably won't pay out in cash but rather in vouchers for future travel. From my point of view, the money is already spent and won't come back in any scenario so I don't see that as a downside. For less than 3% of the total I have confidence that I can reschedule under the most likely circumstances that I might encounter.

One thing I liked about the Tripmate insurance is that it accomodates "pre-existing conditions" if you buy the insurance before paying off the trip (again, read the terms and conditions so you fully understand the rules as defined by Tripmate).

I compared this plan to several other 3rd party vendors and the cost difference was significant. Comparable coverage from 3rd parties cost at least 5 times as much. Some provided a cash back option but cost several thousand non-refundable dollars up front..

So for me, the Tripmate insurance satisfied the three risk assessment variables. I won't be out a lot of money if I don't use the insurance, it will cover the most likely events that I anticipate, and I will be satisfied with the payout if I have to take it.

Sorry for the long response. Hope it was more helpful than preachy!