That Time I Had Almost Everything Stolen in Maui

Small Hawaiian airplane
The small plane we were flying on!

In 2008, I spent three weeks in Hawaii with my boyfriend at the time. The plan was to spend our first week in Oahu, chasing down LOST filming locations. Our second week would be spent hunting down adventure on the Big Island, and our final week would be all about relaxing on the laid-back island of Maui.

For the first two weeks, everything went to plan. I was having the time of my life, bodyboarding on some incredible beaches, whale watching until I threw up, taking a helicopter ride over an active volcano, and hanging out at a luau. I had high hopes for our final week.

My string of bad luck began with our flight to Maui. We were flying on a 8-seater plane and I had a debilitating fear of flying. There were only two other passengers on the flight, which made for a bizarre experience, to say the least.

When our designated flight time rolled around, the pilot greeted us at our gate and led us over to the plane. While he stowed away our luggage, we clambered inside. Seeing all the controls in the cockpit was terrifying.

small plane in maui airport
The small plane we were flying on!

It was a windy day and the landing of the plane was dramatic. We swerved violently from side to side, as the wind blew it off course from the runway time and time again. I exchanged nervous glances with my boyfriend and dug my fingernails into my armrest. I squeezed my eyes shut and took a deep breath.


My eyes snapped open in horror and I saw us racing safely along the tarmac. Okay, so it wasn’t exactly bad luck, but it was an awful experience in a string of further awful experiences.

welcome to maui sign

We rented a car and set off to drive to our apartment.

We travelled only 10 miles down the road before my boyfriend noticed something strange. He told me he felt as though we had a punctured tyre. We pulled over and, sure enough, he was correct. We turned around returned to the airport.

Car number two. After checking all four tyres were pumped full of air, we threw our luggage in the back and climbed inside.

No air conditioning? Mud everywhere? Cigarette butts in the ashtray?

We promptly climbed back out again.

Car number three. Perfect. We climbed inside and set off for our apartment. Again.

Thirty minutes into our drive, my boyfriend slammed on the brakes and we squealed up onto the sidewalk.

“Lauren,” he said.


“I think I left one of our bags at the airport.”

My jaw dropped and I gaped at him in horror. A walk around to the boot proved he was correct. He had left one of our bags at the airport.

It was our smallest bag.

It was our most important bag.

In this bag, we had a laptop, both of our cameras with all our photos, our passports, and our money. There was now a very real danger that our dream holiday was going to end up ruined.

I wasn’t surprised to find that, upon returning to the airport, the rental car company claimed we hadn’t left anything behind. Funnily enough, they claimed not to have security cameras in the parking lot. There was nothing we could do.

Unfortunately, there’s no happy ending to this story. Nothing was ever handed in. We lost all of our photos apart from the ones I’d uploaded to Facebook. We had to replace our cameras and laptops, and our travel insurance didn’t cover more than around $300. We had to apply for emergency passports.

We tried our best not to let it spoil our holiday but the devastation was in the back of our minds, too.

The most upsetting part of this trauma was the loss of our photos. We took thousands of photos and videos of our trip, and lost them all.

So learn from my mistakes

Never carry cash around with you, and especially don’t keep it in one place. Take as much as you need and keep it in several different bags.

Back up your photos! (We did do this on our laptop, but as that was stolen too we lost everything!) Buy an external hard drive (I’ve used this 1TB drive for three years of travel and it’s great), and use a service like Crashplan to keep the contents of your laptop online.

Make sure to have all of your belongings with you at all time!

Share this post:

Previous 6 Months Until I Leave to Travel: What Am I Supposed to Do?
Next Exercises to Prepare for Long-Term Travel


  1. Mike Lenzen
    January 25, 2011

    Good to hear that you still enjoyed the trip without your electronics and cash. What insurance company were you using? I’m still shopping around for medical and travel insurance. It sounds like you didn’t have much trouble making a claim, a good thing when dealing with an insurance company.

    • Lauren
      January 25, 2011

      Hey Mike!

      I was actually using insurance that I got with my credit card from Natwest… I’m currently looking for insurance companies for my trip at the moment, and so far World Nomads looks to be one of the best companies!

  2. Sunee
    January 26, 2011

    Wow, what a terrible way to end off a holiday. Well, I always say you need to experience these things first to learn from them (although it might seem like common sense, it usually isn’t). One more thing, I’ve learned to backup my photos online instead of on an external that might get lost or damaged as well. There are loads of free sites where you can do that and a few that you pay a minimal fee for the benefit of not losing resolution sizes.

  3. Dave
    November 4, 2014

    Hi Lauren. Awesome article post on the travel insurance. My wife and I are about to go backpacking in South East Asia for 4 months and we have been trying to sort out the travel insurance on a one-way ticket. We are having challenges to find a company that provides this for backpackers. I am trying to arrange something with World Nomads for the two of us and I was wondering if you used them, and if you could share how the experience was like? Any tips would be helpful :) Thanks in advance!

    • Lauren
      November 19, 2014

      Hi Dave,

      Yep, WorldNomads are absolutely who I’d recommend — I’ve used them for three years and have been very happy with them! I wouldn’t go with anyone else! :-)

  4. Ron
    January 2, 2016

    I’m so sorry you lost so much in Maui – I’ve been lucky enough on my travel to not have lost anything yet **knock on wood** but I did have a few friends who didn’t keep an eye on their things and end up losing a camera down in Costa Rica.

    Naturally, not quite a dramatic experience as yours, but it’s never pleasant losing that kind of gear on the road!

Leave a reply

Your email address will not be published.