Travel Insurance Might Save You

But Only if You Choose Carefully

Every year, we have guests who have to cancel their trips. Usually, the reasons are sad and unexpected — a sick parent, a hurricane, a broken arm. It’s always regrettable, but with the right insurance, you can avoid losing a lot of money, as well as losing your vacation.

The Pitfalls of Most Travel Insurance

As I found out with trip cancellation insurance purchased for my father, most plans cover very few circumstances. In his case, his incoming flight from Rome was cancelled due to weather, which meant he missed his connecting domestic flight. When I tried to use the insurance purchased on Expedia, it turned out that it did not cover weather events.

Similarly, if the weather is bad, but the roads are open, you will not be covered. If they air is unhealthy due to smoke, but the area is not evacuated, you will not be covered. If you get sick, but do not get a doctor to certify your illness, you will not be covered. If you are a caregiver and need to cancel you trip to take care of someone who is not on the trip with you, you will usually not be covered. If you get divorced, you might be covered, but if you break up with the person you’re living with who is not your legal spouse, you’re not. If a parent dies, you’re covered, but if a pet or dear friend dies, you’re not.

As I have found out in looking at trip cancellation insurance, the typical policy covers almost none of the reasons that have ever caused me to cancel a trip and probably only about a quarter of the trips our guests have cancelled.

Getting the Right Trip Cancellation Insurance

There are, however, policies that are worth the price. What you are looking for is “Cancel for any reason” policies. These policies will cost extra, but they cover you for almost any reason. However, typically you must

  • Purchase the policy relatively soon after purchasing your trip, typically within about two weeks.
  • Ensure your entire trip — air travel, accommodations, etc
  • Purchase it before a reasonable person would be able to guess that there will be a need to cancel (i.e. before there is an official hurricane forecast, for example).
  • Cancel your a specified amount of time before departure, typically 2-3 days.

But if you meet those criteria, you have a lot of leeway. You had planned on skiing, but it’s a drought and there’s no snow? Covered. Have asthma and it looks like there will be smoke from a wildfire? Covered. Have too much work and just can’t get away in the end? Covered.

Now, in this case, “covered” means something on the order of a 75% or a 50% refund, depending on the level of coverage you select.

Purchasing Cancel for Any Reason Travel Insurance

We do not have a recommended provider, but we have found a few sources of Cancel for Any Reason Trip Insurance online. For better or worse, we have no relationship with these websites and provide them for information only.

  •  Squaremouth is a comparison shopping site, not an insurer, like Kayak for airfare and Bankrate for loans. They have a lot of Cancel for Any Reason policies to choose from.
  • TravelGuard from insurance giant AIG also has Cancel for Any Reason policies.
  • TravelEx offers Cancel for Any Reason upgrades on their Travel Select policies.

There are probably many more options to choose from, but that should get you started. If you have a good or bad experience with any of these, or have a company you highly recommend, please let us know.

Insurance Not Included

When we first started in this business, cancellations were quite rare and we almost always made exceptions to our cancellation policy. After a couple of years with lots of cancellations, we realized that had become the de facto insurer for our guests.

We have always tried to implement a few basic principles in our business:

  • Treat people like we would like to be treated.
  • Start from a position of trust (in other words, don’t create rules for the sake of creating rules).
  • Be fair to everyone.

By acting as the insurer for our guests, we were taking on all the risk of cancellation. When we decided to cancel a trip to Glacier National Park at the last minute because of fires, we realized that we did not expect a full refund and that it was nor fair to the rental owner to ask for it. He was, after all, willing to provide the lodging he had promised. Unlike a hotel that can overbook and count on a few cancellations, we can’t do that. When someone cancels on short notice, that typically leaves us unable to fill those nights. 

If you can’t afford to forfeit your trip costs, we now strongly recommend that people purchase supplementary insurance. 

When our guests need to cancel at the last minute, we try to be fair. We do our best to rebook the property and to pass on any money we take in to the guest. But we strongly recommend that guests do not count on this, especially on very short notice.