Well, it depends on how you define vacation, (we call them holidays here). Does it have to involve going away? I had a vacation as in time off work a couple of weeks ago. Whereas most people zoom off to exotic places and lie in the sun.. or they holiday somewhere nice in the UK... I spent 2 weeks having my ceiling pulled down and replaced. You have never seen such a mess. If I dusted and cleaned once, I did so a million times, it was awful! I'd say that was the most miserable vacation I've ever had.. I was shattered every day, aching all over..
Other than that.. the only one I can think of was.. .as a kid we rarely had holidays away, but for a while there my dad took us away for a week to the Isle of Wight, (a small island off the coast of the UK). The trouble was, he could not really afford it and hadn't paid the full amount so the owners of the hotel were bugging him for money, and he had no money at all to take us anywhere. But even so, I think it was considered still to be a good vacation as just to be away was a treat and there was always sea and sun.
My wife and I went to Maine two years ago with my sister and her husband. It was a nightmare. We rented a small cabin and they immediately claimed the bed instead of flipping a coin. My brother-in-law only went to get the weed, which he thought was legal there and it wasn't. He bitched the whole time. The two of them bickered constantly, then accused us of doing so, which we did not. They were stoned almost all the time, then bitched about me drinking. They left earlier than us and left the cabin for us to clean up. There were numerous other things. We didn't speak for almost a year.
Visiting in Winnipeg while I was on leave from Naval base in Halifax I got pick-pocketed and had to hitchhike back. I was boozing too much and not having much of a great time anyway.
I sliced my finger badly just before leaving on my trip. I wrapped it tightly and held my hand up above my heart for hours to keep the blood from gushing out. I got on the plane which was fine but when I went to use the restroom, the previous person in there had covered every surface with diarrhea. I had to change planes in Amsterdam on a tight schedule, I was unfamiliar with that airport, nothing was marked and I barely made my connecting flight. When I got to Madrid and up to my hotel room, it was not yet cleaned. I met up with my friend who was coming from another country and we met in the lobby. Minutes later, someone came rushing in with the news of what was happening back home. It was September 11, 2001. My friend, had developed a drinking problem in the years since I had last seen her in person and was slightly inebriated the whole trip and she was not a pleasant drunk. There are a lot more details, but you get the picture.
Never had a worst Holiday, now I hae had some experiences crafted by comedy writers.
1. Was in Malaga for Holiday. While there we decided to go over to Morocco on a day trip. Took the tour option big mistake. Instead of seeing the sites we saw every Tourist Trap and Trash and Trinkets shop in Marrakesh. Waste of a day and money.
Same trip listened to a group of Seasoned Citizens complain about everything in Spain on the way to and from the Ferry. The biggest complaints were the topless and nude Sunbathers, the husbands were getting distracted. The food was the second biggest complaint.
2. Was in Osaka when a Typhoon hit. Instead of seeing the sights, we were hunkered down in our hotel and restricted from Going out. Pretty interesting watching the winds do massive damage.
3. General rule anyplace where there are hordes of Chinese Tourists. There sharp elbows and constantly posing for selfies I find less than appealing to be around. Throw in their disrespect and rudeness makes for a disgusting situation
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