Once you’ve decided to buy travel insurance for your Getaway (and we strongly recommend you do — see our main travel insurance article for the why and the how-to-buy), the next question is which policy. Not all policies are created equal, and the wrong one can leave you exposed when you most need coverage. Here’s what to look for.
Pick a policy with real trip-cancellation coverage
The core thing a travel insurance policy should do is reimburse you if you have to cancel your trip for a covered reason — illness, injury, family emergency, jury duty, and so on. Make sure the policy you’re buying covers the full non-refundable cost of your Getaway. Cheaper policies sometimes cap reimbursement well below your actual trip cost.
Consider “Cancel For Any Reason” (CFAR)
Standard policies only cover cancellation for specific listed reasons. Cancel For Any Reason is an optional upgrade that lets you cancel for any reason at all — you changed your mind, your dog got sick, work blew up. It usually reimburses you for 50–75% of your trip cost rather than 100%, but it’s the only protection that covers truly unpredictable cancellations.
One catch: CFAR has to be purchased within 14 to 21 days of your first trip deposit (the window varies by insurer). If you wait until the trip is paid off, you can’t add it. If CFAR matters to you, buy your policy soon after booking.
Pre-existing condition waiver
If you or anyone in your party has any pre-existing medical conditions, look for a policy that includes a pre-existing condition waiver. Most insurers offer this only if you buy the policy within 14 to 21 days of your first trip deposit. Without the waiver, a flare-up of a known condition can be excluded from coverage.
Make sure medical and evacuation coverage is generous
U.S. health insurance often doesn’t cover you abroad, and Medicare definitely doesn’t. A good travel insurance policy should include at least $50,000 in emergency medical coverage and at least $100,000 in emergency medical evacuation coverage. Evacuation is the expensive piece — getting airlifted from Portugal to a U.S. hospital can run six figures.
A note on credit-card “built-in” trip insurance
Many travel credit cards advertise built-in trip insurance as a perk. The coverage is usually real but limited: lower dollar caps, narrower list of covered reasons, often no medical evacuation, often no CFAR option. For a domestic weekend trip, credit-card coverage can be enough. For an international group trip with a non-refundable resort booking, it’s usually not. A dedicated policy is worth the cost.
When to buy
The short answer: as soon as possible after your first trip deposit. The CFAR window and the pre-existing-condition waiver window both close fast (14 to 21 days). Buying early also means you’re covered if something happens between booking and traveling — not just on the trip itself.
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