Travel insurance sits in an odd spot for most travelers: cheap enough that skipping it feels like a rounding error on the total trip cost, yet abstract enough that it's easy to buy on autopilot without ever checking what it actually covers, or to skip entirely on the assumption that nothing will go wrong. Neither approach serves you especially well. The honest answer to "is it worth it" is that it depends heavily on the trip, what you've already got covered through other means, and what specifically you're insuring against, so it's worth spending fifteen minutes actually thinking it through rather than defaulting to a habit in either direction.
What travel insurance actually covers
Most standard policies bundle together several distinct kinds of protection, and it helps to separate them because you may need some far more than others. Trip cancellation and interruption cover reimburses prepaid, non-refundable costs (flights, hotels, tours) if you have to cancel or cut a trip short for a covered reason, typically illness, injury, a death in the family, or sometimes job loss. Emergency medical coverage pays for treatment abroad, which matters enormously in countries where your domestic health insurance either doesn't apply or applies with major gaps and exclusions. Medical evacuation coverage, often sold as a separate add-on, pays to get you to adequate care or home if you're seriously injured somewhere remote, and can run into the tens of thousands of dollars if paid out of pocket. Baggage and personal-item coverage reimburses lost, stolen or delayed luggage, and is generally the least valuable component per dollar spent, since payouts are often capped low and require substantial paperwork.
When it almost always pays for itself
A few scenarios make travel insurance close to a no-brainer rather than a judgment call. International trips where your domestic health insurance provides zero or minimal coverage abroad are the clearest case: a broken leg requiring surgery in a country with an out-of-pocket private healthcare system can easily run to five or six figures, and even a routine ER visit in some countries costs more than an entire year of travel insurance premiums. Expensive, heavily prepaid trips, like a paid-in-full luxury tour or an expedition cruise, also tip the math firmly toward insurance, since the potential loss from a cancellation is large relative to the policy cost. Remote or adventure travel involving activities like high-altitude trekking, scuba diving beyond recreational limits, or expedition travel to areas with minimal local medical infrastructure is another case where evacuation coverage specifically is close to essential, not optional, given what a helicopter evacuation from a remote trailhead actually costs.
When you can reasonably skip it
On the other end, a short, cheap, fully refundable domestic trip where you already have solid health coverage that applies at your destination is a much weaker case for a separate policy; the premium may cost a meaningful fraction of what you're actually insuring. Travelers who already have annual multi-trip insurance through a credit card, an employer, or a standalone annual policy are also frequently paying twice if they buy a new single-trip policy for every booking, so it's worth checking existing coverage before assuming you're starting from zero.
Credit cards and existing coverage: check before you buy
A significant number of premium travel and rewards credit cards include some form of trip cancellation, delay, or rental car coverage automatically when you book with that card, and some also include baggage delay and even limited medical coverage. The catch is that the details vary enormously between cards and are frequently more limited than a dedicated travel insurance policy, both in dollar caps and in what counts as a covered reason for cancellation. Before buying a separate policy, it's worth pulling up your card's benefits guide (not just the marketing page, the actual policy document) and checking three things: whether cancellation coverage exists and what reasons qualify, whether medical coverage exists and what the cap is, and whether evacuation coverage is included at all, since many cards omit it entirely. If your card's existing coverage is solid for your trip type, a standalone policy may only be worth adding for the medical and evacuation gaps rather than full replacement.
How to actually choose a policy
If you decide a standalone policy makes sense, the decision usually comes down to a handful of concrete questions rather than picking whichever option is cheapest. Does the policy cover cancellation for the specific reasons most likely to affect your trip, and does it offer a "cancel for any reason" upgrade if flexibility matters more to you than cost? What's the medical coverage cap, and is it enough for the destination's actual healthcare costs, not just a number that sounds large in the abstract? Is medical evacuation included, and to what dollar amount? And does the policy cover any higher-risk activities you're actually planning, since many standard policies quietly exclude scuba diving past a certain depth, skiing off-piste, or other "adventure" activities unless you pay for a specific rider. Comparison sites that let you filter by these specific coverage types, rather than by price alone, make this a five-minute exercise rather than a guessing game, and reading the actual policy document rather than the summary page is worth the extra ten minutes for any trip where the payout would genuinely matter.
Filing a claim: what to keep along the way
The single biggest reason legitimate travel insurance claims get denied or delayed isn't fraud, it's paperwork. Insurers generally want documented proof tying the claimed event to a covered reason: a doctor's note for a medical cancellation, a police report for theft, an airline's official delay or cancellation notice for missed connections, and receipts for anything you're claiming reimbursement on. It's worth taking photos of receipts as you go rather than hoping a paper trail survives a two-week trip, and keeping a simple folder, digital or physical, for anything that might become relevant. For weather or airline-caused disruptions specifically, get written confirmation from the airline of the cause and duration of the delay before you leave the airport, since verbal explanations from a gate agent don't hold up in a claims review. None of this is complicated, but doing it habitually is what separates a claim that gets paid smoothly from one that drags on for months over missing documentation.