Southwest Didn't Reimburse Canceled Hawaii Vacation Costs

Did Southwest Reimburse Canceled Hawaii Vacation Costs?

Southwest is in the process of making amends with one million passengers who suffered when the company had a nearly complete meltdown because of antiquated technology following a huge winter storm. Some passengers continue to be unhappy about how Southwest handled their canceled Hawaii vacation costs.

This comes as Southwest attempts to right the issues that occurred. Bob Jordan, company CEO said, “On behalf of Southwest, I want to let you know we’re so sorry. I know no amount of apologies can undo your experience.” Southwest is also offering at least some passengers 25k Rapid Rewards points as a gesture of goodwill.

He also said that customers will be receiving refunds, and the company is hoping to reconnect the remaining passengers with their baggage by the end of this week.

Canceled Southwest Hawaii vacation passenger pleads for help.

Amy Dougherty of Denver planned a Hawaii vacation. She indicates she bought it through Southwest Airlines. That would probably mean she bought it through a company called Southwest Vacations, which isn’t the same company as Southwest Airlines.

Amy is pleading for help from Southwest Airlines, the US Department of Transportation, or anyone else who will listen. She claims that “Southwest Airlines offered to pay us 1/4 of what we paid for our Hawaii vacay that we booked thru them and didn’t happen. So much for lip service about making things right. Who can help?

Passenger Dave Helfen pleaded for help, too, about his return from a tropical vacation, as you’ll see below.

Takeaways to protect your Hawaii vacation.

1. We don’t usually buy trip insurance domestically but…

Trip insurance is a must for international travel. For one thing, without it, you may have no way of getting back to the US if something goes wrong. In addition, virtually all health insurance is invalid when traveling abroad. So for us, it is a no brainer to have it.

Domestically, on the other hand, we have almost never purchased trip insurance. For one, it is relatively expensive and generally can cost up to 10% of the amount insured. Then too, in most cases, there’s no need for additional health insurance in Hawaii. But when vacation rentals or other advance purchase nonrefundable costs are involved, it could be smart to either cover those through trip insurance or avoid prepaid Hawaii vacation costs to circumvent the need for trip coverage.

2. Plan for the unexpected. It can happen.

Who in their wildest dreams could have imagined the systemwide Southwest collapse that occurred over the holidays, wherein most of their flights were canceled? Moving forward, this will serve as a reminder not to be complacent about such things.

You may recall that editor Jeff has had multiple things happen on trips. His luggage was lost by two airlines, including Delta. In that case, even though their baggage tracking is online (which Southwest is not), it took three days for him to actually reconnect with his luggage when a flight was canceled due to mechanical issues, and he was rerouted differently than his luggage. He needed to buy clothes, among other things, and his trip insurance paid all of those costs with minimal hassle. Jeff was cavalier and only had slippers with him on the plane. Bad mistake, as he had major hiking planned on the trip, which necessitated finding new hiking shoes immediately upon arrival.

3. Know who you are dealing with.

In this case, Amy may have incorrectly believed she was purchasing her entire trip from Southwest Airlines. But in reality, Southwest, like other airlines, partners with companies to sell vacations under their brand, including airfare, accommodations, car rental, etc. Apple Leisure Group is the company that owns Southwest Vacations. It also owns United Vacations.

Another Southwest Vacations traveler got stuck in this mess. Dave Helfen said he was traveling from Cancun. “Flight cancelled home from Cancun on Christmas Day – Been on hold for 3 hours and also waiting for callback from #southwestvacations to modify itinerary and it never came. Gave up and had to book another way home – all we needed was a little help.”

4. When things go awry, take control immediately.

People who seemed to fair the best in the Southwest debacle are those who acted proactively on their own behalf, immediately making alternative plans. They did not rely on then overwhelmed Southwest to come to their short-term rescue. Lesson learned.

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24 thoughts on “Did Southwest Reimburse Canceled Hawaii Vacation Costs?”

    1. Hi Sherri.

      Why would you buy trip insurance from an airline? Look at a trip insurance provider—far, far better options.


    2. Creditcard used to book flight may provide trip insurance.

  1. Yet another reason I despise SWA. Many have given me grief for being a HA apologist on this forum and all I can say is you get what you pay for.
    Will continue to always fly HA when I go visit the mainland.
    Happy new year gentlemen


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