Tag: newyork

I’ve been caught out more times than I’d like to admit — overpriced flights, surprise fines, poor planning. You name it. I’ve learned most of my travel lessons the hard way. That’s why I want to share not just the highlights, but the disasters too. Maybe it’ll help you dodge a few headaches of your own.

One of my most stressful travel days happened in America, and honestly, it still makes me cringe a little thinking about it. But let’s get into it — maybe you’ll laugh, maybe you’ll wince, but hopefully you’ll walk away a little wiser than I was.

It all started with a simple plan. We’d just finished a road trip through New Jersey and had a flight booked to Florida the next day. A friend had recommended a third-party site called Kiwi. I figured, sure, why not save some money?

We booked a cheap motel for the night, dropped off the rental van, and I thought we were golden. But oh, how wrong I was.

Let me just say: if you’ve never stayed in a dodgy roadside motel, count your blessings. The lock on our door barely worked, there were cockroaches in the bathroom, and the sheets looked… questionable at best. I was lucky to be with friends. If I’d been solo, I don’t know how safe I would’ve felt. I’d stayed in plenty of budget hostels before — most were clean, welcoming, even kind of fun. But this? This felt straight out of a true crime documentary.

Still, we made it through the night. Just barely.

Check-out was at 10 a.m., and our flight wasn’t until 4 p.m. We debated paying for a late check-out, but figured we’d tough it out at the airport. In hindsight, that $20 would’ve been a bargain.

We arrived early, camped out near an outlet, stocked up on snacks, and tried to settle in. At first, it felt like part of the adventure. Uncomfortable, sure, but fun.

Then things started to unravel.

The first blow: at check-in, I was hit with an unexpected $60 fee for my bag. Kiwi hadn’t sorted the hold luggage correctly, and while the airline said I could maybe claim it back, it was already clear that this wasn’t going to be easy.

Next came a wave of delays. There was a hurricane on the horizon, we were hoping our flight wouldn’t be cancelled because of it. Hours passed. We got hungry, cranky, and sore from sitting on cold plastic seats.

We travelled through the airport, chatted with vendors and explored. And just when we thought we might finally be boarding, the flight was cancelled entirely, due to a pilot shortage. It was now almost midnight.

We were exhausted. Barely functioning. But there was a glimmer of hope — they managed to rebook us on another flight that night. The catch? It was from LaGuardia Airport. Over an hour away. In the middle of the night. We were told by the gate agent that our Uber would be fully reimbursed. It was something, at least.

But when we got to the customer service desk, everything changed. Suddenly, they were only willing to cover $75 of the $125 ride. And it was now past midnight.

This is where I thank my past self for travelling with a brilliant friend. She’d recorded our earlier conversation with the gate agent. When we played it back, the mood at the desk shifted fast. The staff claimed the recording was illegal. The tension in the air was sharp, almost heavy.

Now, I don’t like confrontation. It makes my chest tighten and my mouth go dry. But something in me clicked. I calmly pulled out my phone, looked up the state laws, and found that the recording was perfectly legal. I didn’t raise my voice or argue. I just said, “I’m happy to delete the recording, but only if you follow through on what was promised.”

There was a long pause. Then a sigh. Then finally… a free Uber 🎉🎉.

We walked away with our Uber covered and my hands still shaking from the adrenaline. We’d been at the airport since 10 a.m., and it was now creeping toward 1 a.m. I felt like I’d aged five years in one day.

The rest of the journey went surprisingly smoothly — or maybe I’d just mentally checked out by then. Honestly, I barely remember boarding. Next thing I knew, I was waking up hours later in Florida, strangely refreshed and mildly confused.

But it wasn’t over for me yet.

Later, when I tried to claim compensation for the cancelled flight, I ran into wall after wall. Because I’d booked through a third party, the process was near impossible. Endless forms, follow-up emails that went nowhere, and radio silence when it came to actually getting my refund. I fought hard. I got nowhere.