Travel Insurance: An Honest Guide

Travel Insurance: The Honest Advisor’s Guide

Travel insurance is the thing people buy and hope they never use, and the thing people skip and then panic when something breaks. The honest version is: you usually need it, but you need the right kind — and the cheapest policy is almost always the worst deal.

What Travel Insurance Actually Covers

The category breaks into four things that matter:

Trip cancellation. If you have to cancel before departure for a covered reason — illness, death in the family, job loss — the policy reimburses the non-refundable cost of your flights and hotel.

Medical evacuation. Emergency evacuation if you’re injured or seriously ill while traveling internationally. These can cost $100,000 or more on a charter medical jet from the wrong end of the world. This is the coverage that earns the entire insurance category.

Lost or delayed baggage. Covers the actual loss or significant delay of your luggage — emergency replacements when your bag doesn’t show up.

Travel delay. Covers costs if your flight is delayed long enough that you need an unplanned hotel night, meals, or onward-transport changes.

Three Scenarios Where Clients Were Glad They Had It

Medical emergency abroad. Your husband gets appendicitis in Paris. You’re not thinking about price — you’re thinking about getting him care immediately. The hospital wants payment upfront, in euros, in a number that’s not on your credit-card limit. Travel insurance with medical evacuation covers emergency hospitalization, and if the situation is serious enough, it covers emergency medical transport home. A medical evacuation flight runs around $100,000. Your insurance pays it.

Trip cancellation for the right reason. You book a $6,000 honeymoon in the Caribbean. Two weeks before departure, you find out you’re pregnant and your doctor says international travel isn’t safe at your stage. You cancel. The resort doesn’t refund. The airline doesn’t refund. Travel insurance reimburses the full non-refundable cost — the entire $6,000. The math justifies the policy with one trip.

Lost or seriously delayed baggage. Your luggage doesn’t arrive for four days. You’re in Europe with no clothes, no toiletries, no medications. Travel insurance covers your emergency purchases up to a coverage limit. Most clients never use this benefit. The ones who do remember it forever.

What’s Not Covered (And Where People Get Burned)

Pre-existing medical conditions — unless you buy insurance within a specific window of your initial trip deposit. This is the most common claim-denial trap and it’s entirely avoidable.

High-risk activities — mountaineering, skydiving, off-piste skiing — generally aren’t covered without a rider you have to add explicitly.

Travel to countries your government has issued advisories against. If the State Department says “do not travel,” your policy will use that as a reason not to pay.

Claims from your own negligence. You left your camera on a train. You walked into a known dangerous neighborhood at 2 a.m. The insurance company will fight that.

The Credit Card Question

This comes up constantly. If you have a strong travel rewards credit card — Amex Platinum, Chase Sapphire Reserve — your card likely includes some trip cancellation and baggage protection. That’s real coverage.

But most credit-card travel insurance is secondary. That means you have to file your claim with the credit card company, and they’ll fight you on what’s covered. Standalone travel insurance is primary — you file directly with the insurance company and they pay. The process is faster and less adversarial.

Real scenario: your father has a heart attack three days before your international flight. You cancel the trip. Your credit card’s trip cancellation coverage says a parent’s illness is covered if your parent is traveling with you. Your father is home in the hospital, so the credit card denies the claim. A good standalone policy covers it. That’s the difference, in real money.

Planning a trip and not sure what coverage you actually need? Start with a 30-minute discovery call — insurance is one of the first things we talk through, because it’s the foundation everything else sits on.

The Cheap-Policy Trap

A $29 travel insurance policy is almost always a bad deal. High deductibles. Low coverage limits. Narrow definitions of what qualifies. A medical evacuation cap of $50,000 is insufficient — if you’re seriously injured skiing in Switzerland and need to be flown home on a medical jet, you’ll spend close to $100,000. The $29 policy isn’t covering it.

Here’s the math. If your trip costs $8,000, decent travel insurance costs $120 to $200 depending on your age and coverage level. That’s about 1.5 to 2.5% of the trip cost. If something goes sideways, the insurance saves you the entire $8,000 — sometimes more. That’s a clean return on investment.

When To Buy It

The moment you make your deposit on the trip. Most policies have a 10-to-14-day window from your initial deposit during which pre-existing conditions waivers apply. Wait past that window and the waiver isn’t available — pre-existing conditions become uncovered. Buy early.

When You Can Skip It

Truly short domestic trips. A three-day weekend in a neighboring state where you have a car and can return home easily — skip it.

But the moment you’re flying internationally, the moment your trip costs more than a few thousand dollars, the moment you have pre-existing health conditions that might cause you to cancel — buy it.

What To Look For

• Medical evacuation coverage of at least $250,000
• Trip cancellation that covers your actual trip cost (not a capped percentage)
• A reasonable deductible — not $1,000, which defeats the purpose
• Emergency evacuation coverage that includes transportation back to the US
• Baggage coverage that’s actually useful — not a $500 limit on a trip where you’re packing camera equipment or formal-event attire

Read the Fine Print on Covered Reasons

Some policies are narrow (“illness diagnosed after you purchased insurance”). Others are broader (“illness that causes you to be hospitalized”). The difference determines whether your claim gets paid.

For my clients, I default to AirMed & Tours — the carrier I’ve found is competitively priced, comprehensive on coverage, and most importantly fast and reasonable on claims. Insurance you have to fight to use isn’t insurance worth buying.

The Bottom Line

If you’re traveling internationally on any trip with real money in it, you need travel insurance. Not the cheapest policy. The right policy.

If figuring out which policy that is feels like work, book a 30-minute discovery call — we’ll structure your insurance as part of the trip-planning process, so you’re covered before you’re booked.

Book Your Free Discovery Call →︎

Last updated: April 2026. I keep this guide current. As insurance carriers and policy structures shift, the page changes.