My First Long-Distance Southwest Flight: Honolulu to Louisville

In October, I’m doing something I’ve never done before—I’m flying Southwest Airlines from Honolulu all the way home to Louisville (SDF). A long-haul Southwest flight? Yep, I’m giving it a try. Why? Because the price was just too good to pass up—$376! 🤯

Now to be clear: that price only included bags because I’m an A-Lister. My husband? He’ll be paying to check his. I’ve been a loyal Southwest flyer for over 20 years, and while I’ve loved the perks of being A-List—early boarding, free bag, the familiar chaos of the boarding poles—I’ve been struggling with some of the recent changes. ✈️💼

I mean, one free checked bag is nice, but I want two. I’m a shopper. And I also want to bring a carry-on and a backpack. Did I mention I’m a shopper? 😅

The “no seat assignment” thing has never really bothered me. I don’t mind lining up by a boarding pole. But that’s going away too. Soon, Southwest will be assigning seats and charging extra for better ones—just like everyone else. It feels like the end of an era.

Still, I’m adjusting. I’m even flying with a plane change in Phoenix—and I’m not bothered by it. I’m just making sure all my devices are charged, because I will miss the seat-back TVs you get with the legacy carriers. But hey, when you’re flying home from paradise, a few trade-offs are worth it. 🌺

So here’s to trying something new, embracing change (even when it’s not your favorite), and getting the most out of your travel dollars. I’ll let you know how it goes—and whether I’d book a long-haul Southwest flight again.