Nothing as awful as many of these, but have had some incidents...
Flying to Croatia on Jet2. Two attempted landings and each time returned to Venice due to storms. On the third attempt, same, and this time the air crew had run out of hours. Sunday evening in Venice airport, as Jet 2 attempt to organise an international bus transfer. We did manage to get a group together for a €130/head taxi, but which was good as we got to our accommodation by 2230. The people who relied on Jet2 were abandoned at a deserted airport at around 3am (and had to wait for car hire desks to open / transfers to start at 8am.
Arrived in Marrakech having pre-booked a transfer to our riad accommodation. Taken to the less salubrious side of the Medina, we were the abandoned by the transfer driver, because he couldn't find our accommodation in this maze of narrow pedestrian alleys. A stranger found us, and got us to our accommodation. The transfer driver turned up and demanded his tip, and only went away when yelled at by both the kind stranger and the riad staff. The same holiday I caught food poisoning (not from the riad, the food there was lovely), and ended up spending New Year's in bed drinking luke-warm peppermint tea.
Driving holiday around Portugal. Booked an AirBnB on the outskirts of Sintra. Finding it was a challenge as Sintra is a maze of one way roads. We arrive (late) at some locked gates and have to work out how to contact the host. She appears and lets us in to the basement of her architect designed house. She's divorced; the basement used to be her husband's studio, and wasn't really designed as guest accommodation - makeshift kitchen area, office style bathroom, vast open plan space. The biggest problem was that it was freezing cold - an amazing space at warmer times of year, but not great for a New Year's break!
The final one I don't remember a lot of. Family touring caravan holiday where I was probably 6 and DB 4. It rained a lot, and to top it off, both of us came down with chickenpox. My poor parents!