I will be honest with you. For years, I treated travel insurance like a boring checklist item. You know how it goes. You book a trip, the website asks if you want insurance, and you click yes just to feel responsible. Then you move on with your life and forget about it until something goes wrong. That was me until two years ago in the Dallas-Fort Worth airport.
My flight from a smaller regional airport was delayed by mechanical issues. Nothing dramatic, just a three-hour wait on the tarmac while they fiddled with something under the hood. I was not worried because I had built in what I thought was plenty of connection time in Dallas. Four hours felt safe. It was not safe.
By the time I landed, my international flight to Mexico had already closed its doors. The airline agent at the counter shrugged and told me the next flight was not until tomorrow morning. When I asked about a hotel, she pointed to a sign about weather delays and said, ” That is your problem.
That night cost me $340 for a hotel room near the airport, meals, and transportation back in the morning. The airline did not pay for any of it. My travel insurance? Well, I had not actually read the policy. I just bought whatever default option came with the ticket.
Here is the thing about missed connection coverage that most people miss. It is not just about flights. I learned this the hard way, but now I actually read the fine print before I buy. When you have proper coverage, and your first leg gets delayed by something covered in the policy, the insurance steps in. We are talking about reimbursement for a new ticket if you need one.
A hotel room if you are stuck overnight. Meals while you wait. Transportation between the airport and that hotel. All of those little costs that add up fast when you are stranded. But here is where it gets tricky. And this is the part that surprised me when I started researching after my Dallas disaster. Every insurance company defines a qualifying delay differently.
Some policies say three hours is enough to trigger coverage. Others make you wait six hours. A few policies I looked at recently only cover delays caused by specific things like weather or carrier mechanical issues, but they might exclude things like air traffic control delays or crew shortages.
When you are standing at the customer service desk trying to figure out your next move, the last thing you want to think about is whether your specific delay reason qualifies under your policy’s missed connection coverage terms. If you have ever been on a cruise, you know the ship leaves on time. It does not wait.
I watched this happen to a couple in Barcelona a few years ago. Their flight from Paris got delayed by a strike, and they arrived at the port two hours after the ship departed. The look on their faces still sticks with me. Here is what they discovered. The cruise line does not care about your flight delay. They will not refund you. They will not send a boat to get you.

Your options are either to fly to the next port and catch up or go home and lose the whole vacation. That next port option can get expensive fast. We are talking about last-minute flights to Caribbean islands or Mediterranean cities, plus hotels, plus meals, plus transportation to the actual port. I have seen these costs hit three thousand dollars for a family of four.
That is not a fun surprise. Good missed connection coverage written for cruise itineraries specifically will cover those costs. But you have to check the policy language. Not all travel insurance treats cruise departures the same way they treat missed flights. I think people ignore missed connection coverage because it is not dramatic.
Emergency medical evacuation sounds scary and important. Trip cancellation protects your whole investment. Lost baggage coverage means you are not wearing the same t-shirt for a week. Missed connection just sounds like a minor inconvenience. But here is a question for you. When was the last time you needed medical evacuation versus the last time your flight got delayed? Exactly.
The underwriting logic here actually makes sense when you think about it. The really damaging financial events in travel are often the boring ones. A six-hour delay that makes you miss your connection and requires a new ticket and an overnight stay can easily hit a thousand dollars.
Do that in a foreign country where you do not speak the language and have no idea how local hotels work, and suddenly that coverage you skimmed past feels pretty valuable. I am not an expert on everything. I still get confused by insurance terminology sometimes. But I have learned a few specific things to check when I buy a policy now.
That is nothing compared to what you might spend if things go wrong. Next time you are buying travel insurance, and you are clicking through those policy details, stop for a minute on the missed connection section. Read it. Think about your specific trip and what could go wrong. Ask yourself if the coverage matches your risk.
Because standing in an airport watching your plane leave is bad enough without also watching your wallet take a hit. Trust me on that one. For a deeper dive into comparing policy details, this guide from the International Travel Insurance Journal breaks down the differences between providers pretty well.
References
U.S. Travel Insurance Association. (2023). Travel Insurance Consumer Survey.
Federal Aviation Administration. (2023). Air Travel Consumer Report. U.S. Department of Transportation. https://www.transportation.gov/airconsumer
Cruise Lines International Association. (2023). State of the Cruise Industry Outlook. https://cruising.org/en/research-and-data
National Association of Insurance Commissioners. (2022). A Consumer’s Guide to Travel Insurance. https://content.naic.org/sites/default/files/publication-trvl-lp-travel.pdf
