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Three Men on the Worst Vacations They’ve Ever Taken

Whether it’s a hurricane, a crappy rental or a friend that drives you fucking crazy, there’s always something that can ruin your best-laid travel plans

Vacations: They’re supposed to be fun! That’s the whole goddamn point. But when they go wrong, they can go really wrong, as we found out by talking to three guys whose trips — one romantic, one family, one with buds — took a serious turn for the worse.

The Hurricane Cruise

Carey Kelly, 28

My wife and I both worked full-time jobs and it had been an incredibly stressful few months. This cruise was our long awaited vacation — we had gone on one before and fell in love with cruising. This was a short one, only five days, leaving out of Galveston with stops in Cozumel and Progreso, Mexico.

We had taken note of a storm in the Gulf but weren’t really worried about it as all the forecasts showed it not developing. We heard nothing from Carnival, so we didn’t think anything of it, but we knew it was more serious than we thought right after we left because the captain got on the speaker and told us that we would be swapping our ports due to the storm.

The boat started rocking the second day, then got worse from there. There were times when it was funny, like watching the water in the pool splash out, and times when it wasn’t funny, like having to make sure your glass stayed upright at dinner. It was impossible to walk in a straight line down the hall, we would constantly be hitting the walls. Sleeping was also interesting: The rocking was kind of peaceful, until you had to get out of bed.

I got really sick. I spent the majority of my time on the ship lying in bed or throwing up in the restroom. I quickly found out that I was not alone. The second night of our cruise was formal night: My wife and I love getting dressed up, so I got my suit on and we made our way to the dining room. Unfortunately, our table ended up being in the back of the ship. Such a beautiful view, except you could feel — and now see — the boat rocking. I ordered my food, trying to keep it together, but I ended up having to run to the restroom to throw up. I heard another man doing the same thing in there. From our room steward to the comedians and the bartenders, the rocking became a running joke.

When we docked in Progreso, my first thought was, “Good, I can stop throwing up now.” We went to some shops and got some food. When we got on the restaurant’s WiFi, that’s when we really saw how powerful the storm — Hurricane Michael — had become, that it was getting really close to us, and that it was not going to get better from this point. Other than that announcement from the captain, though, there were no official comments about the storm. We were basically skirting around the edge of a hurricane the entire time! Luckily we brought our own Dramamine, but I heard other people say that they had to buy it from medical, which I found crazy.

One of the main things we were super excited for was the shows. On our first cruise, we didn’t find the shows until the night before we got off, so this time we made a point to go watch all of them. A show on the first night was amazing; the second night we noticed that the lights hanging over the stage were swinging a lot — like, enough to make you question if they were going to stay up there. The cast came out and apologized to the crowd, saying that they wouldn’t be performing due to safety reasons, so a lot of the shows were just the cast sitting on stools and singing. We spent a lot of time in the casino (I’m sure the boat could be taking on water and the casino would still be open).

Once we got back to Galveston, I think the thought of having to go back to work outweighed the rocking, so it became a normal “it’s time to get off the boat” feeling rather than an “I need to get off this boat” feeling. Actually, we’re currently planning to go on another cruise in January — hopefully far away from any hurricanes.

The Buzzkill Friend

Josh, 47

Two friends and I planned a surf trip to Costa Rica. We’d gone on trips like this before and I invited another guy along on this one. Let’s call him Dave: He was a friend, and I thought it’d be cool to bring him on his first surf trip. So there were four of us, but right off the bat, the other two weren’t that stoked Dave was coming.

We had these big cockroaches coming into the house we’d rented, and that drove him crazy the whole week. Dave would be stalking around the house with a broom and flinging them outside as the rest of us were kicking back. He was the only one stressing about it: I mean, it was a surf trip in Central America, the rest of us were almost admiring how big the roaches were. We also had a lot of ants, so every night he was like, “Arggggh, fucking ants!”

The first night, we got into a heated debate about something stupid: If you were stuck on an island would it be healthier to be stuck with butter, or peanut butter? But Dave took it way too seriously — he must have argued about it for an hour. The second night got heated again, too, this time about religion. It just wore everyone out.

The surf was great, but Dave kept getting in the way of some local guys. Their boards even hit one time. He was ruining everyone else’s surf one day because he would be in position for a great wave but wouldn’t go for it because he was scared, so it’d just pass by.

The last day, he drank the last of our water all for himself.

A taxi was supposed to come pick us up at 11 a.m. to go back to the airport. No worries, no problem: Our bags were packed, we were sitting on the front porch talking about what an awesome trip it had been. Dave was sitting off by himself, tapping his foot on the ground, looking at his watch, then walking to the end of the driveway, looking down the road, walking back, sitting down, tapping his foot, looking at his watch. We were like, “Dude, relax, the guy will be here.” He was like, “No. He’s not coming! I’m going to fucking lose my job!” The rest of us were just laughing at him. The taxi arrived maybe five minutes late, if that. 

For our flight back to the U.S., the other two guys missed the flight because their boards couldn’t get loaded on to the earlier flight. I got up and helped argue their case. Dave, though, just stayed in the plane, like he was ready to go. When we all got back to the States, my other friends were like, “Dude… don’t ever bring that fucking guy anymore.”

The Airbnb From Hell

Thomas, 38

It was my birthday, and I wanted to drive to L.A. and spend the weekend there with my wife and kids. I planned a weekend of restaurants, museums, sightseeing, the beach and all that. It was an amazing plan, but I was still being an idealistic parent about what’s actually possible with small kids. I got an Airbnb near the beach — it looked like something out of a magazine and the owner seemed cool, it was almost too good to be true.

On the drive up there, my wife realized she forgot about half the stuff she was supposed to bring for the kids. The kids weren’t napping, they spilled water everywhere in the car, and of course the traffic was bad. When we finally got to the house, there was a sign saying “No Parking” where I was told the parking spot was. So I texted the owner and he said, “Oh, yeah, that’s no longer a parking spot. I forgot to update the listing.” So I had to find street parking about a half mile away.

The place seemed nice — at first. A lot more beat up than in the photos, but still cool. Then my wife went to the bathroom and saw shit on the toilet bowl. We texted the owner and he insisted that “the cleaner came.” The kitchen was filthy, too — stuff was mostly put away, but it wasn’t at all clean. Meanwhile my older son was playing outside on the patio and tripped on a huge hole where a paver was missing, splitting his chin open.

Eventually we went for a walk and quickly realized that a double stroller wouldn’t fit on the sidewalks. We found a nice restaurant in the neighborhood that would take us, but they wouldn’t let us take the stroller inside. The bill was $350, and my son got an allergic reaction to his meal.

On the walk back, my son stepped in shit of some kind. The other one was crying nonstop. We put the kids to bed in different rooms but when we checked the windows, we realized that none of them actually lock shut — we were on the ground floor.

My wife, upset and exhausted, went to lie down on the master bed. But she quickly realized the sheets didn’t seem to have been changed. Within five minutes our bags were repacked and we were on the road back toward home. I can’t remember what I did the rest of the weekend.

Happy fucking birthday to me.