Worst Travel Experiences in Key West

I have shared bits and pieces of this story with friends, family, and my writing network, but never in the realm of "worst travel experience ever." It's kind of a misnomer, though. While the travel experience itself was horrible, it was still one of the most enjoyable trips I've ever taken...sounds strange, but chalk it up to my having a good ability to let things go, move on, and deal with things.

In the fall of 2008, my husband and I went on our honeymoon to Key West, Florida. We had loaded my bank account full of all the money we'd need rather than splitting it (we didn't yet have a joint account) and we began our trip with a flight from Cincinnati to Miami.

We landed in Miami. The weather was beautiful and we got a cool rental car to drive to the Keys. It was nighttime, so as we first ventured down to Key West, we got to enjoy the eeriness of driving down a road completely surrounded on both sides by black water.

We had booked a reservation at a place I considered to be a hybrid between a hotel and bed and breakfast. Small and quaint, but with the typical amenities of a hotel. We arrived in Key West at around midnight. No one was working at the hotel, but that was ok. We grabbed our key from the lock box and entered our room by the pool.

Everything was great. For the first day at least.

It became the worst travel experience when I woke up on our second day in Key West. My legs itched. I looked down at them and was shocked. They were chewed up with bug bites from ankle to waist. We assumed I was bitten by bed bugs, so we went to discuss the situation with the hotel staff. We were met by the snottiest front desk woman I had ever seen. She practically picked a fight with me saying it must have happened at the beach. I calmly explained to her that we hadn't yet made it to the beach...that we were, in fact, planning to go to the beach that very day (before I realized my legs had holes in them like Swiss cheese). She continued to argue with me, vehemently denying that the hotel could have any part in this nightmare of a travel situation.

Fortunately, a manager arrived shortly after the whole situation started. She also asked if we'd been to the beach, but at least when I said "no," she accepted my answer and moved on. She offered to have the staff check the room for bed bugs. She said it would take around a half hour, so we went for a walk to pass the time. Of course, it felt like 100 degrees outside and it made my legs itch like crazy. But I sucked it up, more concerned that bed bugs were infesting our stuff.

When we got back, the hotel manager informed us that there were no bed bugs. I was happy that was the case, but I was confused as to what had been chewing up my legs. She offered to give us a room on the second floor. We decided to take it, and I didn't end up with any more bites, but the ones I had also didn't go away for a week. We finally figured out that it must have been sand fleas that got in under the door in our first hotel room, which was right next to the pool.

Anyway, had that been the only mishap, it wouldn't have been the worst travel experience ever. The next day, we decided to entertain ourselves by walking around Duval Street and having a few cocktails. We ended up stopping at two places before we settled in at a place called Sloppy Joe's. After a few drinks, we decided to move on and grab dinner. There was only one problem. The waitress had my debit card, but she had left for the evening.

See, in the Midwest, a lot of bars hold on to your credit card until you get ready to leave. Then they either run that card or ask you to run a different one if you prefer. When we'd sat down at a table, I handed her my card and she didn't bring it back. When she left, we ended up with a second waitress who had no idea my card had already been taken. And so began the drama.

Rather than believing me, the waitress told me the restaurant's policy was not to hold on to cards. I responded by informing her that, while it may not be the policy, it happened. She then asked if I could've left it somewhere else. I said, "No," and that I had used cash at the other places we'd visited throughout the day. This whole cycle was getting us nowhere, and I was increasingly getting upset that there was an obvious lack of thinking the customer was always right about anything.

Finally, a manager came to join the fun. We went through the same set of questions we'd been through with the waitress. He had called the first waitress and couldn't reach her. At this point, I was concerned that this chick ran off with my card on purpose and was now having a night on the town with our vacation money.

Finally, my husband accepted that we could have somehow left the card somewhere else. So he revisited every location while I sat at the bar doing nothing, eating nothing, and drinking nothing. After about two hours dealing with this situation, we finally decided to cut our losses, pay the bill with a credit card, and leave. We gave them my cell number to call if the card turned up.

At about 2:00 the next morning, I got a call from a different manager saying they'd finally reached the waitress, who she had in fact accidentally walked out with my card. Well at this point, I'd already called my bank to cancel the card because I thought it was purposely stolen. And with my bank, you can't reverse it. To make this travel experience worse, Key West didn't have either of our banks, so we couldn't do any kind of transfers or check writing for cash.

After being unable to access my bank account other than by writing checks and losing $50 to a check cashing place, I cut my losses and decided we could charge some of the trip to our credit cards, but I hoped my limits were high enough for the trip. At the time, neither of us had long credit histories, so we didn't have 1000s of dollars to spare on the credit cards.

The rest of the week seemed to go off without any hitches until the day we were supposed to drive back to Miami and turn in the rental car. There was a flash flood that morning that washed over many of the roads. Our rental car was in a parking garage that was flooded, and trying to get it out was a tricky venture because one wrong slide would've tanked it into the guard rails. By the time we'd gotten the car out of the garage, which took two hours, and we were able to load it with our suitcases, I knew we'd be late turning the rental car back in. By the time we made it to Miami, we were charged an extra hundred dollars for not having it in on time.

All in all, these mishaps were crazy and frustrating, but at least we didn't have any problems with our flights! I'd still go back to Key West, I just think I'd be more careful about where I stayed and what places I'd frequent. Hopefully, you can learn from these experiences and mistakes and avoid having these kinds of travel mishaps on your own vacations.