Oyster.com Editors Share Their Biggest Travel Disasters

See recent posts by Maria Teresa Hart

You've made your plans, booked your trip, and set off on what should be a highlight reel of gorgeous sunsets, memorable meals, and great company. And then -- disaster strikes: Your wallet gets nabbed; your car breaks down; or you're checking into the ER instead of the hotel. This is why the gut-punch of a travel disaster is so very hard to take. Just when you should be feeling on top of the world, the world sweeps your legs out from under you and puts you in a headlock.

As travel editors here at Oyster.com, we've been through countless disasters in our journeys. So take it from us, that which does not kill us makes us stronger (and smarter) travelers. Or at least makes for fascinating happy-hour stories. Check out some of the travel fiascos we've survived below.

1. Breaking a Leg — Literally

“I once visited New York City with a broken leg — and it was fabulous. We exclusively took cabs (no subway for me that trip!) and I had various travel companions wheel me around museums, demanding we go from one end of the Met to the other, never moving a muscle. But this was the silver lining — the downside was that I broke said leg on a camping trip to Hawaii just a few weeks before. Not only did we wait to determine I should see a doctor over 24 hours after I heard the crack when falling off a surfboard, but I also had to cut what would have been a two-week trip short by 10 days, and take the long flight back to Virginia with my X-rays and crutches as my sole companions.” — Jane Reynolds, Senior Editor 

2. Getting Lost in Death Valley


“I’ve told this story countless times, but it still gives me the chills every single time I recount it. Here goes: A few summers ago, my boyfriend and I set out for a month-long cross-country road trip. One of our stops on said trip was at Death Valley, which came highly recommended. ‘The flowers are beautiful,’ ‘Plan to spend a few hours there,’ ‘It’s a can’t-miss’ were among the comments we heard. So, on our way we went. We stopped at a gas station (the only one until you’re out on the other side, apparently) for some food, water, and fuel. The attendant encouraged us to splurge on some extra food and water — we laughed it off, but obeyed orders. Upon arriving in the desert, it was 115 degrees. So hot, in fact, that we could spend only a few minutes outside (just enough time to snap a couple of photos atop a sand dune) before rushing back to the car to find relief in the AC. But that’s when things got really interesting. Our already overworked Honda Civic — a real trooper until that point — began to overheat. The only way to fix it? Roll down the windows and turn on the heat. Then, the water started running out. With no soul in sight (we were the only ones crazy enough to trek through the desert in the dead of summer, after all), we were sure the car would break down, leaving us stranded and fending off cougars. (Warning signs indicated there were plenty in the area.) Even worse, we ended up on an unpaved road that our GPS couldn’t track. Little water, hardly any gas, and the heat blasting in already blazing weather — those were the ingredients of a total travel nightmare. Long story short, after a couple of hours, our GPS miraculously picked up our location, directing us back out into familiar territory. Today, that picture of us standing on top of the sand dunes hangs in our apartment as a reminder that the biggest disasters often make for the best stories (and that the two of us can handle any obstacle that comes our way).” — Alisha Prakash, Editor

3. Being Booted at Customs

View of the Maldives from a Seaplane

“I’ve really only had one travel experience worthy of the ‘disaster’ adjective, but it still haunts me. Take one part poor planning plus one part silly foreign laws, and you get the time I was rejected by Maldives customs officers…twice. I can’t complain because I ended up getting to see both Dubai and Sri Lanka, but I certainly will be more vigilant about learning all applicable laws before flying to a foreign country.” — Lara Grant, Associate Editor

4. Having a Passport and Wallet Stollen

“I studied abroad in Italy in college, and before I went, my mom really wanted me to bring some kind of crazy theft-proof purse with metal wire in the handle. I thought she was being ridiculous and refused to bring it. While dining on an outdoor terrace at a restaurant in Trastevere, a child ran under the table and snipped the handle of my purse, which was hanging on my chair. Because I was young (and not the seasoned travel expert I am today!), I made the even more foolish mistake of carrying my passport in my purse (my thinking at the time being that it was safer on my person). Being without money or a passport in a foreign country is never a great experience, and filing a police report in Italy was initially a bit difficult because of the language barrier. Luckily, because I’d made a copy of my passport, I was able to obtain a replacement from the U.S. Embassy pretty easily, so it wasn’t as bad as it could have been — but I had to rely on Western Union transfers to get by for a while. Now in addition to making a copy of my passport, I always leave it in the hotel safe, and split up my money and credit cards in different places so that I won’t risk losing everything at once if I get robbed. My most recent, less dramatic travel disaster was getting stranded in the Miami airport overnight on my one-year wedding anniversary when my flight was canceled — but I was able to turn the experience into a useful story.” — Kelsey Blodget, Senior Executive Editor

5. Being Left Out in the Cold

“I was 12 when my divorced dad decided to take my brother and me on a road trip. ‘The theme of the trip is serendipity!’ my father announced when he collected us from my mother’s and we peeled down the highway. For the next week, we’d be open to whatever adventure came our way — no planning involved. At first, this impromptu style worked in our favor. We bumped into a theme park and declared it fate that we spend the day riding roller coasters and eating cotton candy. ‘Serendipity is the best!’ But once the sun went down, this casual approach to travel came apart fast. There was a lawyers’ convention in town, and every hotel for miles around was booked solid. It was well past midnight when we were turned away from our fourth hotel without a room. My father pulled his car into a parking lot and made another announcement — the three of us would have to sleep here, in the car. Have I mentioned that my father drove a VW bug? Even for a child, it was impossibly cramped. My dad, who could always sleep anywhere, fell into a deep snore sitting straight up, but I remained awake the entire night watching the cold light at 5 a.m. hit the dumpsters. Cars would pull in with waitstaff doing the early-bird shift at the diner next door. They’d glance at our car and give pitying looks. A chilly sadness had settled over our trip, and I decided right then — ‘To hell with serendipity!’ Travel requires research and planning. Things may not always work out, but at least you give yourself the best possible chance that it will. That morning over diner pancakes, I took the map and charted a course away from the convention and toward hotels with vacancies — then I began to plot the rest of our trip with neighboring towns and hotels. It’s possible that somewhere between pouring the syrup over my short stack and mopping up the last buttermilk bite, a travel editor was born.” — Maria Teresa Hart, Editor

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