Fleeing a Hurricane

travel hacking Jul 04, 2024

I wrote a newsletter recently about our upcoming summer trip to the Cayman Islands.

Well, if you’ve been watching the news, you’ve probably heard about Hurricane Beryl.

The hurricane developed in the eastern Caribbean a few days after we arrived in the Caymans.

As each day passed, the hurricane grew in strength and the locals expressed to us great concern that it could be like the devastating Hurricane Ivan that flattened the Caymans in 2004.

We knew we needed to make plans to leave early, especially before the last minute panic that would likely ensue if we waited until the hurricane got much closer.

I was so thankful for travel rewards!

Our plan was to book an additional flight the day before our scheduled departure flight. Then we would watch the weather and determine if we should leave a day early or keep our original flight.

I had originally booked with American (via British Airways) but I couldn’t book another flight the day before because it had pretty much booked up. Many of the carriers had little availability where our family could sit together because people were likely booking last minute flights out.

Thankfully Southwest had a few seats left, so I immediately booked the flight with Southwest points (and used a Companion Pass for one of my daughters). I knew that because we were the last few tickets to get booked, our boarding position would not be good, and we’d probably still all get split up.

To prevent this, I booked my ticket as Business Select, guaranteeing an A1-A15 boarding pass (the first group to board after pre-boarding). Then I used 3 of the 4 free upgraded boarding passes on the Southwest Performance Business card to book the rest of my family in the A1-A15 boarding group.

This resulted in us getting the boarding positions of A3, A4, A5, and A6. So, even though were were some of the last to book, we’d be some of the first to board & be able to sit together on the way back. Whew!

After watching the weather another day or two, we decided we needed to go ahead and take the backup flight and leave the island. The storm had become a Category 4 Major Hurricane and people were beginning to leave before it was too late. The airport would eventually shut down and no flights would be able to leave.

We kept the original flights booked just in case there was a problem with our backup flights & we weren’t able to get out. We knew we could get our points back on the original flights if we canceled them before check-in, 24 hours prior to departure. Once we got in the air on the backup flights & made it to Florida, I got on the free Southwest wi-fi that comes with the Business Select Fare and canceled our original flights in enough time to get our points back.

The hotel was also generous in giving us our points back for the last day of our stay since they knew our reason for leaving was outside of our control.

We loved the Caymans for the few days we were there and hope to visit again soon.

Join us in praying for all of those in the Caribbean affected by Hurricane Beryl.


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