This has never happened to me, I've never regretted any road trip I've done. However, I've been pretty nervous about some of them (usually because of boring people who - unfortunately - were part of the trip), but not to the point of regret.
It's a shame that not every trip we've planned can ever be perfect, isn't it?
Ideas and suggestions for the road trips
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Yes...the main reason was extremely bad condition of the road that drove me crazy. Driving the car was no less than a roller coaster ride. The journey was for 4 hours and it took more than 8 hours to be there. You can also imagine the extent of damage it must have caused to my car. I regretted every single moment of the trip.
I remember one day my family and I went on a road to visit one of my uncles and it was about 8 hours trip. It was fun and all but what really ruined it for me was that I was so car sick, we had rented out an RV but for some reason I felt so sick and vomited. I felt like that the entire way over there and back. Good thing getting to our destination and resting a bit made me feel better and we ended up having so much fun.
Yeah. I have regretted one trip to kodaikanal which is a hilly place in state. We bought our grandparents along with us who were not willing to enjoy and didn't let us enjoy too. It was really frustrating but we couldn't do anything about it. I was very much regretting that trip.