When I was 12 years old, my family along with my best friend's family went on an RV trip down to Key West over the Christmas break. The RV was designed for a family of 4-5 people but we somehow crammed 8 of us into it. A storm system was in the process of passing through and it went down into the upper 30's with a 30mph wind. It was very cold for us. We found the campsite which didn't end up being on Key West, but a different island closer to the mainland that was full of nothing but white trash. Because my friend and I were the oldest children, we got treated the worst. This entailed doing all the cleanup after each meal while everyone else sat in the RV watching tv and eating dessert. We also had to sleep in a tent next to the RV which had a broken mini space heater that was either switched to "off" or it was stuck on "high". But it couldn't be on high for too long because it was a fire hazard to the plasticky material the floor of the tent was made of. But if we turned it off, the tent became unbearably cold. So we had to take turns through the night turning the heater on and off to keep us warm without lighting the tent on fire. For breakfast the next morning, we had to eat outside while everyone got to sit inside and drink coffee and hot cocoa. So we never got any sleep for the whole duration of the trip and our parents yelled at both us for having shitty attitudes the whole time because we were constantly tired. It was bullshit.
While not "from Hell", I went on a very disappointing vacation when I was 6. My parents woke us at the crack of dawn and told us we were going on a surprise trip. A fancy limo picked us up at the house and took us to the airport with all our little pre-packed He-Man and She-Ra suitcases. We had our winter coats all bundled around us because it was the middle of February and as we descended upon the terminal, our parents told us that we were going to Florida!! Now, when you're 6 and your parents surprise you with a trip to Florida, there is one and ONLY one place you could be going. DISNEY WORLD. I started crying like a little bitch in the middle of the airport, I was so excited. Then my parents had the unpleasant task of realizing my exciting, realizing WHY I was excited, and breaking to me that actually we weren't going to Disney World, we were going to stay with one of their retired friends in a trailer park in Fort Myers. It was a long-ass week of cribbage in the trailer and Bob Evans for breakfast.
My vacations have been great, but my parents had a messed up vacation a while back. They won a "free" cruise to the Bahamas, which was a quick boat trip, stay for 3 or 4 days in the Bahamas, and then a quick boat trip back. Before the cruise they fly to Florida, and then Hurricane Sandy makes its way past. 2 days before the cruise, as Sandy is being a pain the the Caribbean, my uncle passed away in New York. So they had to fly to New York from Florida, just after Sandy passed Florida but before it hit New York. Then the funeral home my uncle was in lost power. Luckily my dad gassed up the car he borrowed before everything went to crap. That was about the only good thing that whole week it seemed like for my family.
I have mini hilarious stories from when I was a kid including being forced to sleep in a bathtub in Las Vegas on a family trip cause I kept kicking my younger sister in the bed we were sharing. But the main one is definitely what I referred to in the WDT about cruises. Went on a Royal Caribbean cruise during Spring Break of my senior year of college. Stopped in Grand Cayman, Costa Maya, and Cozumel. In Costa Maya, a group of friends and I purposefully tried to ditch the same people we had seen all cruise for a different beach bar. Except my dumbass friend who is susceptible to any and every tourist trap (he would have gotten his hair braided if he wasn't rocking a buzzcut) gets us set up with a shuttle to some beach bar 15 min away which we get off of only to see every person from our cruise where we spent the day fighting over a few beach chairs and drinking terrible watered down booze while the rapey bartenders kept trying to get girls to do body shots. So the next day in Cozumel, I decide to just follow the crowd. Well my roommate sharing a room with me went on an excursion so I waited for my friends to let me know we were leaving. Cue me sitting in my room realizing its almost 11 and nobody has said anything and the ship is fucking empty. So I sprint off, abandoned (ominous foreshadowing) and have to take a cab from Port of Cozumel to actual Cozumel, a few miles away. Mind you phones are basically worthless so I wandered through Senior Frogs before finally finding my friends at Carlos and Charlies. We then settle into an awesome time, watching the NCAA tournament, eating nachos, getting shithoused before migrating over to the dancefloor. Given this was my first "true" Spring Break (previous ones had been spent at home, at my grandparent's in Florida, and in a BEAUTIFUL condo in Florida...a good 30 min from any sort of partying), I wasn't prepared for the debauchery. Full out sloppy half naked grindfest as everyone is in beach ware. As I was grinding with a really cute Jewish girl from Philly, I look to my right and notice a drunk dude about 3 feet off the dance floor, sitting down...and being orally pleasured by some sloptart as people cheered and clapped. I was in heaven. About 30 min later, Escobar, who was our room attendant who was also trying to get his grind on while wearing an INCREDIBLE t-shirt with 50 cent airbrushed on it, told us it was time to go. We kind of nodded and brushed him off cause he always warned us well in advance. My friend Pat and I continued grinding before noticing our friends were gone. So we go to get our bags...except mine isn't there. My buzz quickly starts to fade as I panic a bit. No worries, Pat has his bag so we leave the bar. We hear the ships blasting horns in the distance and break into a bit of a jog, but there is no fucking way we'd make it there. Pat has no cash, we can't flag a cab. We see tourists on scooters and ask for rides, they quickly and rudely dismiss us. Finally, running down the beach about a half mile, we see locals fishing with their mopeds nearby. I furiously signal and explain our predicament in Spanish, rusty from lack of use and alcohol. But eventually two of them sympathize and we hop on. I speed down the street holding onto the twin sister of Maria from Eastbound and Down and get off at the dock with a quick gracias. We sprint to the gate, Pat flashes his ship pass and goes on, I get stopped and have to talk my way through security, wasting precious minutes. I finally get to the gangplank, where Pat has continued onto the boat to try to find out friends. There I'm forced to talk to security as they radio me in, for an excruciating 4-5 min as they are pulling up the ropes and unhooking ramps. Finally I'm motioned through where my friends were waiting with my backpack and I got on. I walk up to the deck to find the rest of our group, drunk in hot tubs drinking daquiris, wondering where I've been and asking why my name was coming over the loudspeakers. My friend I mentioned earlier than messed up in Costa Maya had taken my backpack with him thinking I forgot it and he was doing me a huge favor. I found out later that night that Pat actually had his debit card but he didn't want to incur any "excessive" fees at an ATM. This cheap fucker also didn't tip any of the staff cause he "didn't budget for it." I relaxed and had fun that night but later had a mini anxiety attack realizing that I was 5 minutes from being stranded in Mexico with no phone, ID, credit cards or money in just a t shirt and board shorts. I shudder to think how many blowjobs I would have had to give to shady Mexican officials just to get access to a phone.
Your parents rented a limo to take you to the airport for a trip to a trailer park in Florida? You Canadians sure allocate your vacation funds humorously.
When I was five years old, my parents packed me and my three siblings into the van and took us to the Rocky Mountains. I got sick and spent the entire drive home puking my sorry guts out. I was a mess, it was hell for my parents. Most recently I was in Puerto Rico for my brother's wedding a few weeks ago, and my vacation was almost fucked in half when the surf stole my glasses off my face, not 10 minutes after going into the ocean. I bought a floating strap for them it turns out that was just wishful thinking. I am very nearsighted and would have been screwed, had I not packed a spare pair of glasses at the last minute.
To be fair, maybe mother nature was trying to tell you to stop being such a dork with strap-on glasses. My vacations have been pretty good on the whole. The only time really bad things start happening is if I travel with other people. Last summer I traveled out west to go to a cousin's wedding and then spend a week in the Rockies. My dad pretty much had a nuclear meltdown after being around me for 24 hours, and he hasn't really seen me since. Then in September I went to Chicago with my then-girlfriend, we got into a bunch of fights ("you ruined my meal because of the look on your face!"), we broke up for a night, and made up as I was about to leave the next morning. I did, however, discover the joys of makeup sex. Oh, and then there was that time in Morocco when I ate something a bit off and spent several days and nights shitting and puking my guts out in Fes. Between that and the constant efforts of everyone to rip you off, I didn't really like Morocco.
The irony is not lost on me, nor is sarcasm easy to read sometimes. The Wal-Mart in Loiza, Puerto Rico had a limited selection of neck straps and you gotta make the best of your situation.
The worst vacation I ever went on was a family road trip to Alabama when I was 12. I was at the height of my tween angst and seriously, who wants to go to Alabama in the middle of the summer (or ever)? As if that wasn't bad enough, my dad had rigged up a little tiny TV in the car, which ought to have made the whole ordeal better, but my sister insisted on switching back and forth between the animated and live action versions of 101 Dalmatians. The worst day of travel I ever endured was a family trip to California for Christmas when I was 9. My sister threw up in the car on the way to the airport and continued periodically all day. We got on our first plane at about 9 am, sat on it for 3 hours on the tarmac, then were told to deplane. We then schlepped across the airport and waited for 2 hours to get on another plane that would never leave the ground. After that, the airline had everyone get in line to re-book flights because they were failing so miserably at getting anyone anywhere. There were 3 desks open for over 200 passengers and of course, my parents with 2 small children in tow, had not gotten there very quickly. We ended up on a flight that left Detroit at about 8 pm and ended up in San Francisco, two hours away from my aunt and uncle's house, at 10 pm. We finally get there, my parents set up a bed for me and my sister to share, and she immediately barfs in it. Needless to say, I cried like a bitch.
To be fair, she didn't barf on me, just in the bed I was trying to sleep in. Still unpleasant but nowhere near as traumatic.
When I was about 10-12 my parents decided we would take a mini vacation out to Montauk for the weekend. We pile up in the car and start driving and hitting the most horrendous Long Island traffic ever. The type where the highway is backed up from one end to the next end. What was supposed to be 3 hour drive turns into a horrid 6 hour drive. Exhausted we arrive at the hotel where we had reservations at sometime between 3 and 4 in the afternoon. Go up to the counter, go to check in only to get informed that the large hotel room we reserved in the main hotel was no longer available because we missed check in, oh but, we would still be billed for it because we missed check in. My Dad already pissed, but not wanting to drive back asks if they have any other rooms available. They inform us that they do indeed but not in the main hotel, but in the cabin area...oh and they have to charge us the same price for the better room, and they are doing us a huge favor for even considering transferring out reservation. We look at the cabin and it is the filthiest most dilapidated thing we have ever seen. My father outright refuses to stay there and goes back to the front desk and demands his money back. They tell us absolutely not because check in was between 12 and 3 and we missed it by 30 minutes. Choice words are exchanged with the clerk and we are soon back in the car for the 3 hour drive back home, the entire way my Dad is on his cellphone with American Express disputing the charges. So, a weekend trip turned into 9 hours in the car and an hour of screaming at a hotel clerk, though we did get our money back.