What's the worst start to a holiday you have had?

Another holiday was a mix of my 20s son and daughter and 2 friends and child driving to a villa in Tuscany. On arrival my daughter decided she wanted to get used to driving the big suv and set off.
Half an hour later she phoned to say the signs were pointing to Florence and how would she get back. I didn't even know our address but luckily one of the boys was able to talk her back.

On a holiday in Rhodes, the hotel reception was unmanned, the food was brought in from a neighbouring hotel on the back of an open truck, the menu had veal every single day, we found cockroaches in the
bathroom, rats near the pool. Holiday rep was unavailable. On day 3, the hotel put notices on everyone's door saying it would be closing the following day, and that we all had to move to a large hotel down the road. That hotel was clean, well-staffed, had good food, but was visited daily by lots of stray cats and dogs (guests felt sorry for them and we all kept feeding them)

My worst start was a trip to Rome back in 2019. I’d booked the wrong return date by mistake and only realised at the airport. Ended up spending nearly twelve hours at Heathrow sorting it all out and missing the first evening we’d planned around the Trevi Fountain. The whole day felt wasted, and dinner turned into a packet of crisps from a vending machine. Since then I always triple-check flight dates the night before travelling.

Our trip to Peterborough for a passport renewal at 6am on the morning of a flight to Italy was a bit hair-raising.
Our flights were from Birmingham and the passports went out of date whilst we'd be away.

Our youngish son (15) was woken as we left and given a wad of money and train times to Birmingham airport.

I was relieved to see him at the check-in.