I’ve traveled a lot—both for business and pleasure—and not every trip has gone smoothly. With Halloween just around the corner, it feels like the perfect time to share some of my travel horror stories. While they weren’t the stuff of nightmares, they were chaotic enough to make me think: If only I’d used Ship&Play.

Whenever I travel, I fall into one of two modes:

  • Mode 1: Beyond exhausted, running on fumes, desperate to crash after a long journey.
  • Mode 2: Running purely on adrenaline, excited to squeeze every second out of my destination.

No matter which mode I’m in, luggage always seems to throw a wrench in the works. Below are three travel horror stories that would’ve gone much smoother with a little help from Ship&Play.

The Commuter Bus Fiasco (New York City Misadventure)

I was traveling alone for work, excited but exhausted after a long day. After landing at JFK—which, for the record, is nowhere near actual New York City—I had to figure out how to get into the city. With the trains down and no desire to pay for an expensive Uber, I hopped on what I thought was a bus heading into the city.

Unfortunately, it was a commuter bus that looped through the city’s outskirts, far from where I needed to be. I sat there helplessly, hoping the bus would somehow get me to my destination. Spoiler: It didn’t. I was on track to end up at the last stop if some kind locals hadn’t stepped in to help me out.

There I was, awkwardly seated with my oversized suitcase at my feet—luggage that screamed I AM A TOURIST. If you’ve ever dragged a heavy bag around public transit, you know how hard it is to blend in. I tried to act casual, but with my luggage and confused expression, I may as well have had a neon sign over my head that said, “Lost.”

If I’d used Ship&Play to send my bags ahead, I could’ve traveled light, asked for directions without looking like a stranded traveler, and avoided the whole “Oops, I’m lost” panic.

Cross-Country Chaos (My First Business Trip)

This story is about my first-ever business trip, flying from Burlington, Vermont, to San Francisco for a conference. Being new to business travel, I was already anxious, so naturally, I couldn’t sleep the night before. Every five minutes, I remembered something I’d forgotten to pack and jumped out of bed to toss it into my suitcase. By the time my alarm went off, I’d managed maybe a single hour of sleep.

At 4:00 a.m., I stumbled out the door to catch a cab, only to arrive at the airport way too early—it hadn’t even opened yet. First in line at security, I had nothing to do but sit at the gate, clutching my carry-on like a lifeline. And I was too paranoid to take a nap, because, who can sleep soundly with a suitcase they have to guard?

During my connecting flight—the attendant announced that they had limited overhead storage and were looking for volunteers to check their bags at the gate. Half-asleep and confused, I dropped mine off before boarding the plane without getting a tag or telling anyone.

Cue the gate agent over the intercom: “WHOSE BAG IS THIS? IT’S TAN, IT’S BLACK—”

Mortified, I scrambled to the front of the line to claim it. If I’d just used Ship&Play, I could’ve avoided the embarrassment—no lugging my bag, keeping watch and no frantic announcements. I would’ve arrived in San Francisco fresh, with some energy to enjoy the trip.

Circling the Streets with a Broken Cooler (Mom & the Cooler Disaster)

Then there was the trip with my mom, which started smoothly—until it didn’t. We took a bus into the city, confident that our hotel was nearby… or so we thought. Unfortunately, my GPS couldn’t figure out which direction we were heading, and we circled the same blocks repeatedly, dragging our luggage behind us.

My mom, the ultimate travel doomsday prepper, had packed a cooler of snacks. Which would’ve been fine, it had wheels, but somewhere in our circles, the cooler’s wheels gave out, and suddenly, we were hauling a broken, lopsided cooler down the street.

When we finally found the hotel, we were sweaty, exhausted, and wondering why we thought this trip was a good idea. If we’d used Ship&Play, we could’ve sent everything (including that cursed cooler) ahead of us. We would’ve arrived at the hotel fresh, ready to enjoy the city, instead of bickering at each other about a dumb cooler.

The Moral of the Story: Travel Light, Travel Smart with Ship&Play

Traveling isn’t always glamorous. It’s often filled with mishaps, whether getting lost, travel anxiety, sleep deprivation, or a broken cooler. But with Ship&Play, you can skip the luggage stress entirely. Send your bags ahead, show up at your destination hands-free, and focus on enjoying the journey instead of fighting with your suitcase.

Next time? I’m using Ship&Play. Just me, the adventure, and the freedom to enjoy my travels.

Erika Austin

Erika has traveled near and far for both work and play, collecting memories, stories—and a few travel mishaps—along the way. Blending humor with practical advice, she shows how shipping luggage ahead can prevent a few disasters along the way.

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