Travel insurance can be a crapshoot; it really depends on the individual circumstances as well as the particular trip one is taking. Basically, insurance is useful when the cost or inconvenience of assuming a risk is a burden for you. As mentioned, many credit cards have some travel insurance as part of the benefits, but be careful, as most issuers have whittled down their coverage—a good example of this is that a number of benefits are now secondary instead of primary. This means that it only kicks in after all other coverage has been paid. This can be reason enough to buy separate travel insurance, as long as that policy is primary coverage instead of secondary. A number of years ago I was underinsured on my automobile policy and so took out a travel insurance policy which included rental car coverage as primary coverage. Everything was fine and nothing happened, so was it a waste of money? Perhaps, but it wouldn’t have been if I had gotten into an accident and my insurance company balked at covering something.
The most common reason for purchasing travel insurance (particularly for international travel) is medical coverage; as stated, it only takes one otherwise minor accident to ruin a trip, or if one has health issues, or—like a friend of mine is—exceedingly accident prone when traveling. Even then it depends on your personal situation; you may have great health coverage at home, but your insurer may balk at paying claims that are out-of-network or are not pre-authorized (which might be difficult to do, if you fall and have a fracture late at night in a place far away from home). In that case, it can be helpful to have an insurer that will just pay for the ER visit no matter what, right off the top.
However, I am in total agreement with everyone who has recommended not purchasing the Amtrak-offered insurance. If travel insurance is needed, one can often purchase a better policy from the same insurer separately. I purchased a ticket today and noticed the “gloom and doom” pitch has gotten more extreme over the past few months. It’s rather ridiculous, since the $17 doesn’t buy much of anything. You can still get ticket refunds or credits in most cases and the coverage only covers the time period for your ticket, whereas separate travel insurance will usually cover from the time you begin a trip with a common carrier at your departure point until the time you end your trip with a common carrier at your departure point. This means all the time you are at your destination/s is also covered. Same with insurance for hotels and airline flights offered through travel services like Priceline and Hotwire; it doesn’t cover enough of anything to be useful except as a profit center for the company selling it.