Travel insurance, explained simply
Why it matters more than any upgrade you could buy — and how to choose a plan that actually pays out.
Read →Travel insurance is the least glamorous thing I will ever recommend, and the one I recommend hardest.
Here's the thing most travelers don't realize until it's too late: your health insurance almost certainly does not follow you abroad. Neither does your ability to absorb a $40,000 medical evacuation from a Greek island, or the non-refundable cost of a trip you have to cancel three days out because your mother is in the hospital.
Insurance isn't about expecting disaster. It's about making sure one bad day doesn't turn into a financial catastrophe on top of an emotional one.
What travel insurance actually covers
Most comprehensive policies bundle several distinct protections. Knowing what each one does is how you stop overpaying for things you don't need and underbuying the things you do.
Trip cancellation
Reimburses your prepaid, non-refundable costs if you have to cancel for a covered reason — illness, injury, a death in the family, jury duty, a hurricane hitting your destination. Note the phrase covered reason. Changing your mind is not one.
Trip interruption
Kicks in once you're already traveling. Covers the unused portion of your trip plus the cost of getting home early.
Emergency medical
Pays for treatment abroad. This is the one people skip and the one that bankrupts them. Look for a policy with primary coverage rather than secondary — primary pays first, without you fighting your domestic insurer for months.
Medical evacuation
Transport to adequate care, or home. This is the expensive one. If you're going somewhere remote — a safari, a small island, a mountain region — do not skimp here. Look for at least $100,000, and more like $250,000 for genuinely remote travel.
Baggage and delay
Useful, rarely the reason to buy a policy. Nice to have when your bag takes a detour through a city you never visited.
The three things that actually determine your plan
Once you understand the components, choosing gets much simpler. It comes down to three questions.
1. When are you buying?
This matters more than almost anything else. Most insurers offer a pre-existing condition waiver — but only if you buy within a short window after your first trip payment, typically 14 to 21 days. Miss that window and any condition you've been treated for recently may not be covered. If you have any medical history at all, buy early. Not later. Early.
2. What are you insuring?
Insure your prepaid, non-refundable costs — not the total value of your trip. Overstating your trip cost means paying a higher premium for coverage you can never claim.
3. How much flexibility do you want?
Cancel For Any Reason (CFAR) is an upgrade that lets you cancel for reasons no standard policy covers — you're nervous, work blew up, you simply changed your mind. It typically reimburses 50–75% rather than 100%, costs meaningfully more, and must usually be purchased within days of your first deposit. For a big-ticket trip with uncertainty around it, it can be worth every penny.
The mistake I see most: buying the cheapest policy on a comparison site without reading the medical and evacuation limits. A $40 policy with a $10,000 medical cap is not protection. It's a receipt.
How to actually compare plans
- Use a comparison marketplace so you're seeing multiple insurers side by side, not one company's pitch.
- Filter by the coverage that matters for your trip, then sort by price — never the reverse.
- Read the exclusions. Every policy has them. Adventure activities, pre-existing conditions, and pregnancy are common ones.
- Check whether medical is primary or secondary.
- Confirm the evacuation limit is realistic for where you're going.
My honest take
I have never had a client regret buying travel insurance. I have had clients regret skipping it. The premium on a well-chosen plan is usually a small fraction of the trip — and it's the only line item that protects every other line item.
Buy it early, buy it comprehensive, and read what you bought.
Questions about any of this? I answer every message personally.
Contact Ley