Look, I’m not gonna lie – when I first started budget traveling, I thought staying at a Sheraton was something reserved for business travelers with expense accounts and people who definitely weren’t sleeping in hostel dorm rooms like I was. Fast forward to last spring, and there I was, checking into the Sheraton San Diego…

I’ll never forget the first time someone told me to look at hotels in Old Town San Diego. I was planning my second trip to the city, still nursing the financial wounds from that overpriced Pacific Beach hotel I mentioned earlier, and my friend Sarah – who lives in San Diego – just casually said,…

So here’s the thing about San Diego – it’s one of those cities that looks deceptively affordable until you start searching for hotels. I learned this the hard way back in 2019 when I decided to spend a week there exploring the beaches and taco shops everyone kept raving about. I naively thought, “How expensive…

So I’m going to be real with you – when I first moved to Dallas in 2019 for a few months of freelance work, I thought flights to San Diego would be cheap. Like, really cheap. Both cities have major airports, they’re in the same general region, and there’s tons of competition on the route….

Last summer, I was sitting in a coffee shop in Chicago’s Logan Square, scrolling through flight prices to San Diego, and honestly? I almost spit out my coffee. $387 for a basic economy seat. For a three-hour flight. I’d literally spent less than that on a week-long trip to Guatemala the month before. Here’s the…

Last Tuesday, I was sitting in a coffee shop in Midtown Sacramento when my friend texted me asking if I wanted to meet up in San Diego that weekend. My immediate thought was “yeah, let me just check flight prices real quick” followed immediately by mild panic because, honestly, the Sacramento to San Diego route…

So here’s the thing about the New York to San Diego route—it’s one of those flights that should be expensive, right? Cross-country, decent airports on both ends, popular destination. And yet, I’ve flown it at least a dozen times over the past few years, and I don’t think I’ve ever paid more than $150 one-way….

Last February, I was sitting in a coffee shop in North Park, scrolling through flight prices to Seattle and nearly choking on my cold brew. $340 for a roundtrip? For a flight I’d taken dozens of times for half that price? That’s when I realized I’d accidentally been searching for flights during Presidents’ Day weekend…

So here’s the thing about Seattle to San Diego flights – I’ve flown this route probably 15 times in the past three years, and I’ve paid everywhere from $39 to $280 for basically the same flight. Wild, right? The difference wasn’t luck, though I’ll admit timing played a role. It was mostly about knowing when…

So here’s a fun story that’ll probably make you feel better about your own travel planning fails. Last February, I needed to get from San Diego back to Phoenix after a week of house-sitting in Ocean Beach. Simple enough, right? It’s the same route I’ve flown a dozen times, just in reverse. I waited until…