Every client I have ever worked with has asked me some version of the same question. Is travel insurance worth it, or is it the line item I can skip?
After nearly 30 years booking travel for clients across six continents, I have always said yes. Last week, I lived it. What started as a quick visit to see my mama in Tri-Cities turned into a trip of firsts, lessons learned, and the kind of cascading travel chaos I never expected to experience personally. I am writing this down before the details fade, because if there is one post that should land in front of every traveler before they book their next trip, it is this one.
The Trip There: One Active Runway, One Missed Curfew, and One Airport Overnight
I took the late flights out so I could work as long as possible on Friday. American had a new connection through Chicago into Tri-Cities, and I was scheduled to land just after midnight. That was the plan.
We pushed back from the gate, jetway already removed, and then sat. Twenty minutes. Thirty. While we were waiting, a passenger in first class stood up to use the bathroom. The flight attendant, who looked like she had been doing this job for about ten minutes, came on the PA and asked the cabin to stay seated because we were on an active runway. He sat down. A few minutes later, another passenger got up. Same announcement.
Then a man two rows ahead of me reached over the seat and flipped her off mid-sentence.
She walked up to him calmly, told him that kind of behavior was not going to fly, and the conversation escalated from there. He was not threatening. He was just disrespectful enough that she made the call to have him removed from the plane. I do not fault her one bit. If a passenger will do that on the ground, you have no idea what he will do at 35,000 feet. They brought the jetbridge back, escorted him off, and we waited another half hour.
Then the pilot came on. Air traffic control at our destination closed at 12:30 a.m. We could still make it.
We took off. We were 20 minutes from landing and already descending through 8,000 feet when he came back on with a sentence I will never forget. We missed it by four minutes. We are turning around and going back to Chicago. By the time we landed back in Chicago, it was 1:30 in the morning. American offered a hotel, but it was 30 minutes away and our rebooked flight was set to board at 6:30 a.m. The math did not work. So I did something I have not done in 30 years of traveling. I spent the night at the airport.
The Admirals Club opened at 5 a.m. I watched the clock from a dim corner of the terminal until then, then waited to board with the few other travelers who had also made the same choice. While we sat at the gate, I joked out loud that everyone better behave because I really wanted to get home to my mama. People laughed. We boarded. Then the pilot came on.
We do not have any fuel.
The plane had sat at the gate all night. Nobody refueled it. He said it usually takes five minutes for the fuel truck to arrive, and it had already been thirty. We finally pushed back around 9 a.m. It was the quietest flight I have ever been on. I think everyone was sleeping.
The Trip Home: A Sinkhole, A Rental Car Hunt, and a Hertz Angel Named Emily
I spent the next few days with my mama. Wonderful visit, great weather, everything was finally on track. I was scheduled to fly home Wednesday.
Tuesday afternoon, a sinkhole opened up on the main runway at Tri-Cities. Twenty feet wide. Seventeen feet deep. By the grace of God, no plane was on it when it collapsed. Every single flight in and out of the airport was cancelled.
I rebooked for Thursday, thinking one extra day with mama was a fine consolation. A few hours later, that flight was also cancelled. The runway repair was going to take longer than anyone had projected. So I pivoted again. Charlotte is two and a half hours from Tri-Cities. I would drive.
Except there were no rental cars in Tri-Cities. None. I called Boone, about an hour away, and confirmed a car. As I was walking out the door to go pick it up, they called back. The car had been taken. I tried Uber. The driver who was assigned to me looked, and I am being kind here, like he was 100 years old and not awake. I called the airport directly and asked if there was anything still on the lot. Hertz answered. Miss Emily had a few cars to give out and a long waiting list of travelers hoping for a one-way rental, and she had one for me. I wanted to hug her neck, but the counter was too high. I was grateful mine came together when it did.
Thursday morning I left at 5 a.m. for Charlotte. My 9 a.m. flight got delayed to 10:47. I finally got home that afternoon.
The Moment That Changed the Tone of the Whole Trip
Somewhere in the middle of all of this, sitting in my mama’s kitchen between cancellations, I told her something I am still thinking about. The enemy was trying to steal my joy, and I was not having it. Travel was going to do what travel was going to do. I could spend the rest of the week angry, or I could go up to Roan Mountain with mama and my sister and worry about Thursday on Thursday.
Roan Mountain is a beautiful state park about an hour from Tri-Cities, and it was a regular picnic spot for our family when I was growing up. June is the only time of year the mountain turns shades of pink and purple, when every rhododendron up there is in full bloom. It is genuinely my favorite time of year in that part of the country.
We went up. The colors were everywhere. We sat with mama and took it in. That afternoon mattered more than any of the rest of it.
I share this because everyone around me, from the flight attendant who got disrespected to the gate agents to Miss Emily at Hertz, was doing the best they could in a situation none of them caused. Being ugly to them would have helped nothing. Being kind got me a rental car at the last minute, an upgraded seat the next morning, and a few moments of grace I am still grateful for.
What Made Travel Insurance Worth It on This Trip
Here is the part I want every traveler reading this to pay attention to. Was travel insurance worth it on this trip? Without question.
The rental car I had to scramble for in Tri-Cities was not in my original trip plan. It was an unplanned expense, about $320 because one-way rentals run high, and I had to put it on a credit card with no certainty I would ever see it back. Travel Insured, the policy I had on this trip, is covering it. The claim is already in motion. By the time the dust settles, I will be made whole on the rental car expense.
That alone, on this one trip, paid for the policy several times over.
A note on how I personally handle this. I carry Travel Insured’s annual plan, which covers every trip I take throughout the year without me having to buy a new policy each time I leave town. For travel outside the United States, I add additional medical coverage on top, because evacuation and emergency care abroad can run into five figures very quickly. You can also add Cancel For Any Reason coverage to most plans, which gives you flexibility that standard policies do not. That is the structure I recommend for most clients who travel more than once or twice a year.
Two other things worth flagging. American refunded the miles I used for the original ticket without me asking, which I think was a nice surprise given how the night had unfolded. And because I booked through a travel advisor, which on this trip was myself, I had someone who knew exactly what to do, who to call, and how to document everything for the claim. That part is harder to put a dollar value on, but it was the difference between a stressful week and a logistical disaster.
If I had been a regular traveler without a policy and without an advisor in my corner, the rental car bill would have been mine to eat, the rebooking would have been on me to navigate, and the claim, if I had even thought to file one, would have been a paperwork nightmare weeks later.
So, Is Travel Insurance Worth It?
Yes. Travel insurance is worth it, without hesitation.
After 30 years, I will tell you what I tell every client. Travel insurance is worth it. It is not the line item to skip. The premium is small relative to the cost of a trip, and the moment you need it, it is the only thing standing between you and a credit card bill that follows you home. Emergency medical coverage matters even more for international travel, where out-of-pocket care and evacuation costs can climb into the tens of thousands very quickly, but even on a domestic trip like mine, the coverage paid for itself the first time something went sideways.
The bigger lesson, and the one I will keep saying until I retire, is that you do not have to handle any of this alone. There is a reason a travel advisor is worth far more than the small commission they earn on your booking. When the runway collapses, the flight gets cancelled, or the rental car company calls to take back the car you just confirmed, you want someone in your corner who has been through it before.
Frequently Asked Questions
Yes. Most travel insurance policies cover trip interruption and cancellation due to covered reasons, including weather, airline-caused delays, and certain personal emergencies. The reimbursement typically applies to unused, non-refundable trip costs and unexpected expenses like rebooking fees, hotels, or rental cars. Policy terms vary, so always read the coverage details before you travel.
Yes, especially when your trip includes flights, prepaid hotels, or rental commitments. Domestic trips run into the same cancellations, weather events, and emergencies that international ones do. A policy on a $2,000 domestic trip typically costs under $100 and can cover thousands in unexpected expenses when something disrupts the trip.
Travel Insured offers strong trip interruption and missed connection coverage, along with options for pre-existing condition waivers when purchased within the required window. They also offer an annual plan for frequent travelers, plus 24/7 emergency assistance, which is what you actually need when something goes wrong at 2 a.m. in an airport.
For the strongest coverage, including pre-existing condition waivers and cancel-for-any-reason add-ons, you typically need to purchase a policy within 14 to 21 days of your initial trip deposit. Waiting longer limits your options. If you are unsure, ask before you book the trip, not after.
When everything goes right, the direct-booking path looks identical. When it goes wrong, you find out very quickly that the airline call center, the resort front desk, and the online travel agency are not going to fight for you. A travel advisor knows the suppliers, knows the workarounds, and is your single point of contact when the trip needs to be rebuilt on the fly.
Ready to Travel Smarter on Your Next Trip?
If you are planning a trip and are wondering whether travel insurance is worth it, or whether to book with an advisor, this is the post I would have sent you before you started. The price of doing it right is small. The cost of going without is the trip you spent six months planning.