JetBlue Will Pay You for a Rainy Vacation—But Should They?

Vacations never go perfectly. Something always goes wrong. Your flight gets delayed. Your hotel has a “surprise” view of the dumpster. Your brother’s sneakers smell so bad, the entire car becomes a biohazard zone. (True story.)

Now, JetBlue wants to pay you if it rains on your vacation. Yes, you can actually get reimbursed if the weather ruins your plans. But let’s be real—some of the best vacations happen when everything goes wrong.

JetBlue teamed up with a startup called “WeatherPromise.” If you book a vacation package through JetBlue and pay extra for this rain insurance, you could get money back if the skies open up.

But it’s not as simple as “Oops, it drizzled—pay me!” No, no. It has to be excessive rain. Like scientifically proven bad weather. They use satellites, AI, and a bunch of fancy tech to determine if your trip is actually ruined. If it is, you can get up to $2,500 back.

Sounds nice, right? But here’s the thing—sometimes, the worst trips are the best trips.

Take my family’s trip to Scotland. It rained the whole time. My sister threw up in the car. My brother’s sneakers smelled so bad, we had to bury his shoes and buy him new shoes just to survive. But guess what? We still talk about that trip all the time.

Then there was the RV trip where my brother blew pepper in my face. Or the Cape Cod vacation where he accidentally lit part of the yard on fire, and I got sun poisoning. (That was a really fun day for my parents.)

Were these vacations Pinterest-perfect? Absolutely not. But they were legendary.

Sure, if you’re really worried about rain. But if you ask me, a little chaos makes for the best stories. So go ahead—book the trip, embrace the mishaps, and remember: someday, you’ll laugh about it.

Even if your brother ruins everything