Four Stories of Travel Gone Wrong

Four Stories of Travel Gone Wrong

Updated August 2, 2023

Thieves Stole our Luggage–and then Called Us

When I was in middle school, my family and I went to Florida. Half-way through the trip, we switched our accommodations. We had all our luggage in the trunk of the car, and headed down to Kennedy Space Center for the day. After driving back up to Orlando, we pulled into a parking lot and I went into the trunk to get my sweater. Everything from the trunk was missing – except a bag of dirty laundry. My dad’s work laptop, suitcases with clothing, keys to our home in Connecticut, my mom’s address book – everything was gone.

We stuck it out for a few days wearing the same outfits we wore in the earlier part of the trip, until the robbers called the house we were staying at. After all, the address and number of the house we were staying at was in our luggage. We bolted out of the house within 45 minutes, and were on a plane back to Connecticut first thing the next morning!

Travel Booking (mis)Adventures

I am a business consultant based in Boston and Milan and do quite a bit of traveling for work…which has made for some, um, adventures.

The most recent was with Expedia. I booked and prepaid a 5-star hotel on the island of Mykonos. When I arrived the hotel said there was no reservation on file and referred me to their agent in Greece, who superciliously offered me a room on the other side of the island. Not satisfied, I informed them that Id be hanging out in the lobby until my room was available.

Well, a room became available and it was- literally- the size of a twin bed. No room on either side of the bed and no window. At $700 a night I was not happy. So I called Expedia in the US. They rebooked me into another hotel. The only problem was that the “other hotel” was in Kos, another island! They thought Kos and Mykonos were “close enough”… problem is there is water, um, between them!?!!

Of course I learned of this after I checked out of hotel A. Needless to say I stayed in a Motel 5.5 (it wasn’t a 6 by any standard) and had to have American Express intervene.

The joys of traveling!

VIP Mix-Up

My girlfriends and I went to Oahu, Hawaii for a fabulous vacation. Everything was going well until we called for a ride to the airport for a quick weekend trip to Kauai. We called “VIP shuttle service” to pick us up at 9am. We informed the front desk of the hotel that we were expecting “VIP Shuttle Service” and to please call us when the driver arrived. At 9:30, we hadn’t heard from the front desk.

Worried, we went downstairs and checked with the hotel. The staff assured us that the shuttle must be late and for us not to worry. We called VIP shuttle service, and the woman on the phone claimed that the driver was at the hotel at 9am, but had left upon seeing no one (guests) in the lobby. She stated that the driver will come back to pick us up. We hurried downstairs and waited in the lobby for our VIP shuttle service.

Within minutes a driver from “VIP” arrived and whisked us away in his car. He drove for about 1 mile and dropped us off at a car rental service. Confused, we asked the driver about the trip to the airport. He told us that this WAS our destination, unloaded our bags and left.

I went up to the customer service rep and asked her about the airport. She repeated the driver’s claim, that this WAS our destination and we are to rent a car if we want to get to the airport. At first we thought she was joking with us and that the real shuttle service would arrive soon. We waited for about 15 minutes, but no shuttle came by. I called the VIP Shuttle Service again and the woman on the phone said the driver went back to the hotel and picked up the intended guest (us). I replied that she was mistaken since *we* are the guests and that *we* are NOT on the shuttle, but at a car rental service down the street.

Here’s what happened: There is the VIP Shuttle Service and the VIP Rental Car Service… They are NOT the same company, but both go by “VIP”. After waiting for about 30 minutes, the VIP Shuttle Service finally came over to the VIP Rental Car Service and we did a guest swap.

The saving grace of this shuttle service fiasco was that our plane had been delayed for 2 hours and we were able to make our flight to Kauai for the weekend! It was an amazing adventure overall.

At Least I Didn’t Punch Anyone

After nearly a year of traveling every single week, I dug deep into my repertoire to surface a travel story that I thought would be fitting. However, I didn’t have to look back very far. It was late October when I found out I would be heading to a little place named Fargo in December. My first thought was, “What in the world did I do wrong to have to go to North Dakota in December?” I proceeded to book my tickets and keep my fingers and toes crossed that it would be a “warm” week while I was there. Little did I know what I was getting myself into.

The week I was there was not too bad, bitterly frigid, but not too bad. At the store that I was consulting for I had been hearing whispers of the consultant (me) that was going to get stuck due to this “perfect storm” that was supposed to hit the Northern US. Needless to say, after not taking my coat off the entire week except to shower I was ready to get out of the tundra more formerly named Fargo. I once again found myself crossing my fingers.

As I left the store I felt my phone ringing and recognized the dreaded 800 number that the ID was showing. It was the Frequent Flier line that calls to tell about cancelations. As the recorded message came on I got sick to my stomach as I heard the words saying that Minneapolis-St.Paul Airport would not be taking flights for the rest of the night.

After another chilly night in my hotel room while the weather outside was -38 (not kidding), I was off to the airport in the morning, where the fun really began. The plane pulled up to the terminal where we received the news that the jet bridge was stuck because it had frozen solid. I felt like telling the desk attendant that, “I don’t really care, I will jump up to eight feet to get on that plane to get me out of here!”

I held my tongue and walked across the airport to the new terminal. Upon arriving in Minneapolis, I laid my eyes upon snow drifts that were literally taller than planes. I arrived to my gate to catch my connection and we were told the plane at the gate was not ours and that it was snowed in. After changing gates 3 times, we FINALLY were able to get on the plane. As I sat, I saw an unusual amount of maintenance workers walking on and off the plane. I knew something else had gone wrong. We then heard the sweet soothing voice of the flight attendant come over the system saying there was a leak in the bathroom pipe and we needed to get switch planes.

At this point I had already misconnected at my next stop. I then rebooked another flight taking me directly to my ending location, but it meant I would need to sit in the airport for 8 more hours. I just took the metaphoric slap in the face and switched my ticket. Once again, this flight got delayed even more. After 12 hours in the airport, I was able to get on the next flight.

You may think this is it, oh no As I watched the flight attendant trying to close the jet door I heard a slam and a crack. “Oooh” the flight attendant said, “If that is broken we will have to change planes.” Doing my best to keep a smile on my face, I laughed and kept watching. I am happy to report that after one hour of talking with repair men and maintenance people, I found the plane in the air.

I got home 48 hours later than I was supposed to. Also, I did it without punching anyone.