I am one who always suggests travel insurance! It's important for all trips, but it's especially important if you're traveling during Winter (snow storms), hurricane season, tornado season, traveling with small children, traveling with seniors, or traveling overseas.
Remember when purchasing travel insurance, check everything carefully. Often, the best rate is not the best deal, so NEVER just buy a policy based on price - it may cost you alot of money in the end. All policies are different, they cover different items, and have different limits. Definitely look at those limits, because there can be a huge difference between policies. And always remember that big name does not mean best policy.
Almost always, independent policies are much better than those offered by the cruise line. And do not buy the policy offered for your airfare by itself. The limits are much lower and some do not include coverage for independent airfare. Make sure to get your policy to include all of your non-refundable travel costs.
And warning; make sure you're purchasing travel insurance and not travel protection! There's a huge difference and it can cost you big time!!
Talk with your travel agent - they can be an invaluable resource on this issue. We use to sell policies from 5 different companies, but fired 3 of them because of their lousy customer service and two of these were the biggest names in the industry!
Now, as for firsthand experience; we always purchase travel insurance whenever we travel, but luckily we've never needed it. As I tell all my clients, you hope that buying it is a waste of your money because if you need it, it's usually not for a good reason. But it's like the saying goes, you'd rather have it and not need it, than need it and not have it!
We were scheduled to leave for 2 weeks to Europe, which included a one week trip to see some of the Christmas markets in Amsterdam, Belgium, and Lichtenstein, followed by a week-long river cruise stopping at various cities on the Rhine to see more Christmas markets.
I had just stepped off the ice after refereeing an adult hockey game. We were in the locker room enjoying our usual after-game libation at about 1:00am when my phone rang. It was my wife telling me our son, who was 28 at the time and living with us, was having chest pains. The rink is only a mile away, so I rushed home, got him, and took him to the hospital. They ran all sorts of tests and finally, after 4 hours, figured out it was his gallbladder! They scheduled him for surgery, so needless to say, we had to cancel our trip. After all was said and one, we got 100% of our $4000 vacation refunded.
I could tell you alot of stories from my clients who have needed their insurance, like the one who flew from Dulles to New Orleans to go on a cruise. They flew in the morning the ship was scheduled to depart. On the way from the airport to the pier, she developed a bad pain in her side. The taxi driver diverted to the hospital where she had to undergo immediate surgery for a burst appendix!
But the worst case scenario happened to a couple who were clients of a friend of mine. Long story short, while on a Panama Canal cruise, the husband had a heart attack. They flew him off the ship to a hospital in one of the foreign countries down there (can't remember which one), where he went into a coma. Four days later, he died. The insurance company was wonderful and helped the wife with all the arrangements, hotels, transportation, bringing the body back home, etc. Total cost; over $100,000!! Total cost to the wife; zero!
Now, before purchasing travel insurance, take a look at your health insurance plan. You may or may not need to have this as a part of your travel insurance. Some health insurance companies handle international claims better than others. Some don't cover anything.
Some credit card companies may include travel insurance or travel protection if you charge your travel. Again, make sure you know exactly what you're getting and what it covers.
While some policies can be purchased up till a couple of days prior to your departure, most companies require you to either purchase the coverage at the time you bought the trip or before the final payment due date in order to be covered for some items, such as pre-existing conditions, financial solvency, or acts of terrorism, among others.
With that in mind, don't purchase the insurance too early. If you're taking a cruise, as an example, and you cancel before final payment due date, you're going to get 100% of your money returned, so there's no reason to get the insurance before then. However, if you're getting a non-refundable airfare, cruise, or vacation, then you'll want to get the insurance sooner.
And lastly, make sure to ask alot of questions; it's very important that you get the right coverage based on your specific situation. Everybody is different and what is good for one may not be good for another.
Obviously, there are alot of questions and misconceptions about travel insurance, so it's extremely imperative you talk to your agent and let them help you to make sure you get what's best for you.
But my best advice is to always get the travel insurance because you'll never know when you'll need it. Hopefully, you never will.