I've run across the question of "Do I really need travel insurance" a lot on travel forums. The way I look at it is if you have the money to walk away from your trip, health insurance that will cover you overseas, and $500k to cover emergency evacuation, then no. Otherwise, then definitely!
While I do not get trip insurance for domestic US trips, I do elect for coverage on all overseas trips. I like the warm fuzzy (i.e., security blanket) feeling I get from knowing that if I get hurt, delayed, or inconvenienced, my trip will be salvageable. How many travelers stuck in Europe in 2010 wished they had trip insurance? While hindsight is 20/20, who could have envisioned Eyjafjallaj would have caused so much chaos?
Most travel insurance policies tend to be customizable for your own level of comfort and selection of options. These options include collision, flight accident, additional medical, cancel for any reason, cancel for work, and sports coverage for prepaid items (greens fees, tickets, etc...). I usually opt for the basic coverage, but if you know of any potential conflicts with work or your personal life, it may be advantageous to consider these supplemental options. The basic rule of thumb to use when selecting trip insurance is expect to pay at least $4 to $8 for every $100 you spend, sometimes more, sometimes less depending on what discounts your eligible for.
Travel Insured International is a company I have used multiple times, but to date I have not actually needed to request a claim. I like their price point and they offer discounts to some customers. For example, their Worldwide Trip Protector plan provides trip cancellation up to the price of the trip, trip interruption up to 150% of the trip price, $750 for trip delays, $50k for emergency medical, $1500 for lost baggage, $300 for baggage delay, and $500k for emergency evacuation or repatriation of remains (hopefully never needed), per person. Make sure you specify how many travelers and their ages when requesting a quote. The good news is that coverage for kids is free.
Here are some of the various vendors offering trip insurance:
My recommendation is do your homework. Decide what coverage makes you happy, then compare pricing. I would even go so far as to call them up and let them fight it out to reduce the price they offer through direct competition. Keep in mind, trip insurance is for your own peace of mind, so select the options that will put you most at ease. You should be worrying about what to try on the menu or which cobblestone street to journey down. It is important to note that trip insurance must be purchased within a very short time (i.e., 7 to 21 days) of when you buy your airline tickets, even if your other costs are undetermined. So keep this in mind before you buy your tickets.
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