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It's hard to say...
India had some of the worst travel moments I've experienced, but also some great ones.
Bali, felt like I was sold a lie. But I ended up hiring a fishing boat and crew and ended up touring a lot of Indonesia.
After balancing the good with the bad, I'd have to say Egypt was the worst. None of the bad was too bad, but it seemed to outweigh the good (even if just by sheer irritation alone, in some cases). With the peddlers harassing you, it's difficult to enjoy what you're there to see. Sticking a giant car park and fast food restaurants next to monuments, takes some of the magic away. The propaganda & false historical "facts" are ridiculous.
Overall, I am still glad I went, but I would never go back.
I got swimmers ear and a fever at the same time halfway through the vacation.
One of the worst was a trip to Colorado. I was about 13, my brother was 10. My dad was taking us skiing and to visit his family in Denver. While skiing, he takes a nasty fall and tears his ACL. He's alone with two kids, and has to figure out how to take care of us. He has to make a six hour drive to get to his brother's house. A snowstorm hits, and the bridge closed. So we sat in a subway for 8 hours while waiting for the storm to pass. Eventually, we get there. We see family, everything is going great. Then our flight gets delayed. And delayed again. And again. We get to the airport; it gets delayed. And delayed. And delayed. We had to sleep on the floor of the airport. My father can barely walk, he's trying to wrangle two kids. We FINALLY get home. The airline lost our luggage. 0/10 would not recommend.
Other worst trip: mother and brother got zika and I almost drowned at sea