This thread is so interesting. I did most of my holidaying abroad pre kids, so at least 15-20 years ago, and loved Florence (it was a cold, rainy January and we felt we had the whole city to ourselves), Dublin, Venice, Krakow, Prague and Costa Rica. We stayed near the train station the first night in Rome and it felt unsafe, but we moved to a nicer area. I wonder how much things have changed in that time?
I liked Paris back then, despite the dirt and rude locals, but we went back last October and I was totally gobsmacked at how friendly and polite the Parisians were, stopping to ask if we were lost, giving us directions, not eye rolling at my terrible French! The streets are still full of dogshit though, but the smell wasn’t so bad at that time of year. Also I love Madeira, swimming in the natural rock pools was amazing and we had an exciting day coasteering with the kids. The wicker couch down the hill was rubbish though!
The only terrible holiday I had was in Thailand. In Bangkok we stayed in a crappy hotel where you could hear cockroaches running around in the bathroom, and see them going up and down adjacent chairs in the bar, and then I got really bad food poisoning at a beach resort and lost loads of weight. Obviously not helped by my then boyfriend being completely unsympathetic and moaning that I wasn’t making the most of the holiday as I couldn’t get out of bed due to feeling so terrible. My mum was really worried about me when we got home, it took me another week or 2 to recover. He was dumped soon after that, the twat!