A client called me from a hospital in Cancun three days into their honeymoon. Not because of anything dramatic, a bad reaction to shellfish, a night in the ER, and suddenly a $4,000 medical bill on a trip that was supposed to be about mai tais and sunset dinners. They had travel insurance. The claim was filed within a week, and they were reimbursed for the medical costs and the two nights of the trip they missed. That call is the entire reason I will never, ever let a client skip travel insurance.
If there’s one rule I don’t bend on, it’s this: every trip I plan gets travel insurance, no exceptions. Not because I get a commission bump from it (I don’t build my recommendations around that), but because I’ve seen exactly what happens on both sides, the client who had it and the client who didn’t, and there’s no version of that comparison where skipping it looks smart in hindsight.
Why This Became My Line in the Sand
Early in my career, I had a client skip insurance on a European trip because it felt like an unnecessary add-on for a “simple” itinerary. Nothing dramatic was supposed to happen. A parent back home had a medical emergency mid-trip, and the client needed to fly home immediately. Non-refundable flights, non-refundable hotel nights, a rebooking fee that cost more than the insurance would have. All of it came out of pocket, on top of an already stressful situation.
That’s the part people don’t think about when they’re deciding whether to spend the extra money. It’s not just about your own health on the trip. It’s about the unpredictable stuff: a family emergency back home, a missed connection that costs you a prepaid excursion, an airline that cancels your flight and leaves you covering an extra night in a hotel you didn’t plan for.
What People Get Wrong About Travel Insurance
Most people think about travel insurance the way they think about a rental car’s extra coverage: an upsell they can probably skip. The difference is that a rental car mistake costs you a few hundred dollars. A real travel disruption, a medical evacuation, a canceled international flight, a hospital stay abroad, can cost tens of thousands.
I also hear the same objection a lot: “But I have travel credit card coverage.” Sometimes that’s true, and it’s worth checking what’s actually included. But credit card coverage is often more limited than people assume, especially for medical costs abroad, and it’s easy to find out the gaps only after something’s already gone wrong.
Where I’ve Seen It Actually Matter
Beyond the honeymoon story, I’ve had clients need insurance for things that had nothing to do with health: a hurricane that shut down an airport and stranded a family for two extra days, a cruise line itinerary change that meant missing a prepaid shore excursion, a lost checked bag with prescription medication inside. None of these are exotic, once-in-a-blue-moon scenarios. They’re the normal, unglamorous stuff that happens on a percentage of trips every single year.
The clients who had coverage got reimbursed and moved on. The clients who didn’t absorbed the cost and the stress, on top of whatever the original problem already was.
Why This Rule Doesn’t Bend
I’m not going to pretend every trip needs the most expensive, all-inclusive policy on the market. What I will say is that every trip needs something, sized to the actual risk of that trip. A weekend domestic getaway has different exposure than a two-week international itinerary with connecting flights, prepaid excursions, and a resort that’s a five-hour drive from the nearest major hospital.
Part of my job is walking clients through what level of coverage actually makes sense for their specific trip, not just handing them a generic policy and moving on. But the baseline, some form of coverage, every time, isn’t something I negotiate on. I’ve watched it save clients thousands of dollars and a level of stress no one wants mid-vacation.
The Bottom Line
I built my business around being intentional with every part of a trip, and travel insurance is one of the few places where I won’t soften that stance for the sake of trimming a budget. It’s the cheapest peace of mind you can buy for a trip you’ve already spent months planning and saving for.
If you’re planning a trip and want help figuring out what kind of coverage actually makes sense for it, that’s exactly the kind of detail I build into every itinerary from the start. Let’s talk through your trip and make sure you’re protected before you ever board a plane.
