Here's the thing. I work in insurance, I Believe in insurance, I purchase only the insurance that I need - to protect my assets ... therefore I have only purchased
trip insurance once (10+ years ago - cruising during the height of hurricane season - and money was WAY more of an issue back then). If I was sailing in upper level verandas or concierge, I probably would very much consider trip insurance - those daily cruise rates are spendy!!) IF I have experienced serious travel issues I might feel differently. And I work in the "back office" - not involved in pricing, risk management, marketing or claims. I'm a geeky Accounting / IT type person. And I work in a "different" industry - Home, Renters, Auto, Farm, etc insurance.
Travel insurance a different type of Property and Casualty insurance than what I am accustomed to, as are Health, Medical and Life Insurance.
What I have looked for in travel insurance when I looked into it in the past
- How much coverage do I really need? And then with the online quoting system: is that per person or total? Do you cover you airline tickets - because presumably, you will make it TO the airport LEAVING for your trip. What about the cost of Excursions - If you don't make it to the ship - will you still be charged for them? DCL say's "you can cancel up to 3 days prior to sailing" but if you don't make it to the ship will you really be charged (I don't know the answer to this).
- How much medical coverage do I want to purchase - AND - what about emergency medical evacuation - is that covered and for how much?
- Is the insurance company high "enough" rated (AM Best B+ should be more than sufficient)
- What to the people here and on cruise critic or other travel sights say is "good" trip insurance - word of mouth usually good indicator (but keep reading my post)
- What does their complaint history look like - check out the Better Business Bureau (or google search them for reviews). And remember, there WILL BE lots of complaints against any insurer of any size - read the complaints for "reasonableness" (look up "Snake Farm" - it's one of the many complaint sites for disgruntled State Farm insureds / claimants - and on the other hand I have friends and family that have had claims with them and I could not believe how much and how fast they paid - my company would have done a lot more investigation).
- Read the Contract, because after all insurance is just a promise: "You give us Money, We Cover your stuff", with LOTS and LOTS and LOTS of exceptions and rules. For example, if you buy insurance when you rent a car, part of the contract says that the coverage does not involve unlawful acts .... like wrecking the car while driving drunk (they won't pay). So Read the Contract to make sure that it seems to cover what you want it to cover. You might have to take some notes and cross check coverages / exclusions - I never said that reading an insurance contract would be easy!!
Some people see travel insurance as more of a necessity. Very Sick relatives, pre existing conditions, etc. And I know that I have a somewhat callous view of what goes on in the real world when I am on vacation. Someone dies - well there's nothing I can do about that. Same with my house - I don't need anyone calling and telling me that it has burned down - nothing I can do about it. My pet has died. I will deal with those type of things when I return home. Callous, but it's my version of reality.
For traveling - our insurance is "proper planning" and building in cushions for delays. I prefer to spend my "insurance" premiums on hotel rooms rather than on the insurance. I do have "other coverages" that would help with some emergency medical & evac costs. So far so good. And I WANT / NEED my Vacation - I don't need assurance that "they" will get me to the next port - and miss a few days of vacation - with more additional stressful traveling.
But with how crappy air travel has become (and did you see that AA is going to be reducing legroom by 2 more inches in many rows and 1 inch in some others just to get 10 more seats on the dang plan!!

- glad that I don't fly them - but other airlines will follow suit) , two days of cushion may no longer be enough.
We've only had our luggage "lost" or more accurately rerouted a couple of times and on the way home!!
We've built in enough time up front to be sure to make it to our destination by the required time (usually a few days before a cruise)
Meals - was going to be paying for those until I got on the ship anyway.
Have not had any medical issues while traveling. If and when that happens - I hope that I am in Europe rather than the Caribbean
And we are mostly a "go with the flow" type of people - so if a hurricane pops up and changes the itinerary - I'm OK with that. Life's an adventure.
WOW - That was a lot of typing -
and I think that I might have talked myself into start purchasing travel insurance again!!