Should You Buy Travel Insurance?

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 in 2018, 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.

Regular travel insurance does not cover a lot of common events:

  • Bad weather, but roads are open.
  • Air is unhealthy due to smoke, but the area is not evacuated.
  • You get sick, but do not get a doctor to certify your illness.
  • If you are a caregiver and need to cancel you trip to take care of someone who is not on the trip with you.
  • 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.
  • And so on.

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.

Cancel for Any Reason Insurance

There are, however, policies that though much more expensive (maybe a lot) are also more likely to be pay out. What you are looking for is “Cancel for any reason” policies. Typically you must:

  • Purchase the policy relatively soon after purchasing your trip.
  • Ensure your entire trip — air travel, accommodations.
  • 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 trip a specified amount of time before departure, typically 2-3 days.

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.

In this case, “covered” means something on the order of a 75% or a 50% refund, depending on the level of coverage you select. So it’s not a get out of jail free card and it can cost a significant percentage of trip costs. Cancel for Any Reason insurance may or may not be worth it, depending on the cost, but at least there is a very high chance of getting some usable coverage.

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. The “better” is that we have no financial relationship with these sites and are not promoting them out of any self-interest other than avoiding uncomfortable conversations with guests that have to cancel. The “worse” is that we have have not actually used them to purchase insurance yet.

  •  Squaremouth is a comparison shopping site, not an insurer. It’s similar to 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.
  • Insure My Trip is an comparison engine like Squaremouth and offers policies with Cancel for Any Reason coverage.

There are probably many more options to choose from and the market is changing rapidly since the SARS-COV2 virus entered our world. Still, that should get you started.

Insurance Not Included with Your Reservation

When we first started in this business, cancellations were quite rare and we almost always made exceptions to our cancellation policy. That has changed over the years as people who are used to hotels came to use vacation rentals more and more.

One of the big differences between us and a hotel is that we cannot oversell. A hotel with 100 rooms, will often take 110 or even 120 reservations for the night. The count on natural “attrition” as people cancel or simply fail to show. If that doesn’t happen, you can show up for your room and find that despite a reservation, they don’t have space for you and they “walk” you (this is why when an area is in a sellout, never be the last one to show up at the hotel).

We obviously cannot take more bookings than we have space for, so cancellations are a lot more difficult for us to handle than it is for a 300-room hotel which can (and usually does) play the odds on cancellations. We think a vacation rental offers a lot of advantages over a hotel, but cancellation flexibility is generally not one of them.

How We Handle Things

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.

When we can’t hold up our end, such as when Covid or fire closes the park, we of course refund fully.

But we can’t offer refunds if the weather is bad or it’s a bit smoky. On that latter point, for example, if the air is Good, Moderate, or Unhealthy for Sensitive Groups, like other lodging in the area, we do not offer a refund. Yes, if it’s in that last category, it will impact the views, but for reference, in 2019, there were 133 days per year that bad or worse in San Bernardino county and 86 days that bad or worse in LA county.

When we feel circumstances warrant, we do try to be generous and focus on the safety of our guests. We don’t lock people into reservations when we feel conditions might not be safe for a given traveler (say, someone traveling with little children during a blizard).

Screenshot of AirBnB reviews
Reviews from AirBnB guests encouraged to cancel for full refund because we thought travel conditions were too dangerous.

That said, when the park is open and conditions are reasonably safe, we hold to the policy in force with whichever listing service you have booked with (it varies depending on how you booked because policies don’t map perfectly between listing services).

We don’t refund for rain, smoke, weather at the point of origin (e.g. your departure airport is closed). We expect guests who book for winter periods to expect to be ready for winter driving.

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. We have on some occasions been able to offer refunds of most fees for guests who cancel at the eleventh hour, but the closer to arrival, the harder it is.

We strongly recommend that guests purchase insurance rather than counting on our ability to rebook and, if you choose not to, give us as much notice as possible so we can do our best to rebook those nights and get you the largest refund we can.