Craziest? Not sure what all qualifies, but in Cabo we went against most rules of thumb. A hurricane was forecast to hit the day we left, so early in our week, we took the rental car to Cabo Pulmo. It was overcast and there was to be rain on the way but not at destination, and not much rain. we had some drizzle in the mountains and then back to sunny. Cabo Pulmo is primitive, getting to it was great fun - gravel road in our compact rental, waiting for steer to clear the road... it was a great experience! completely different way of thinking about a traffic jam. dirt pollution vs exhaust fumes. we stopped many times for photos of steer or cactus. We were not bold enough to be on foot WITH the steer as neither of us are cowboys and wary of wild animals.
Ocean was rough, ex isn't a strong swimmer, couldn't figure out his flippers, etc., so I went to snorkel the largest living coral reef in NA by myself. I am a big buddy system believer but he chose correctly. I was a competitive swimmer from age 4, a lifeguard for a long time, and in plenty of rough oceans so not concerned for saving myself. I only went out far enough to see something, ANYTHING, but of course so much churn I couldn't see much, and didn't stay out long as I was concerned lightning could be on its way as the skies got cloudy .... I generally kept my head down watching fish and waiting for clear so I could see the coral colors but poked up every so often to figure where I was, how far waves took me. I did not want to panic my anxiety-prone ex. If I got into trouble, he would be helpless, although he can speak Spanish! There were few people around and that would be the extent of help. I figured I would have to get back there one day when a hurricane wasn't coming. darn it.
So, we left Cabo Pulmo to get back before dark.
Remember that rain in the mountains? It washed out a road. There was a handful of cars and trucks already stopped when we arrived, in sunshine. We got out, like pretty much everyone else, and walked down to our edge of the water. Already, men were taking off their shoes and wading into the water to find the shallowest part to cross, turning back as they hit waist high. Time goes by, we're all just hanging out in the dessert, locals and tourists, by then many dozen vehicles on each side. Dusk comes and night creatures begin their mysterious noises.
They have located the highest part, some rocks, and some pickup trucks try it, with varying levels of success, but many men in the water helping to keep vehicles moving. We figured we needed to wait until a car as small as ours made it through. That was another hour or two. Eventually I had to, well, urinate, with some urgency. I watched for a while to make sure no direct witnesses, and popped a squat between the open front and open rear doors, feet from a cactus. At least we had excess napkins from picnic lunch and hand sanitizer.
Refreshed, we watched some more until 3 cars our size had made it. We got in line.
The man told us to roll up the windows, and gave ex whatever instructions he gave. We had watched the path of the car in front of us and saw the "spotter men" for the slalom course "boundaries". But, our little car slid off a rock, and they put us back up there, showed us next "hop" to make, and we again were in float position, replaced again, only a couple more hops, and we made them!! WOOO HOOO!!!! GRACIAS GRACIAS!!!
and we're on our way. Far from the tourist corridor, at night, with a vehicle that had just had a wash of undetermined damage. We had enough fuel to go for it and not stop. We made it back to our condo in San Jose without incident. No bandidos, only the generous and hardworking men that helped masses of strangers get their cars through that water.
Whew, that was an adventure!
But wait, still the hurricane, looking like a direct hit, on the day we leave. What should we do? It's a glass airport, that's a creepy place to be for a hurricane, but far enough inland to maybe be ok? Tentative plan, turn in rental car and be prepared to shell out for something we can't foresee. A nervous few days, our tv carried American programming and not weather channel - and no internet - so we relied on resort staff, which turned out to be a perfectly acceptable thing to do! The hurricane was projected to hit higher up the coast so we should be alright. yay! tornadoes, I know what to do. Hurricane in a foreign land? yikes, but not so scared as to cut trip short. Good call, as it turned out. The one thing we should have considered and did not: hurricane rain is going to wash out roads! DOH. it took longer to get to the airport, no total washouts, but not full lanes all the way, either.
Not sure that was the craziest thing I've done, but I sure wish we would have had a pic of the mud covered car before the hurricane rain to prove it. No extra charges on that vehicle, by the way. Thank you, Avis!
I've been to Cabo twice since and haven't made it back there ... but, hey, one of those trips 3 of us took surfing lessons and saw Hotel Cali so certainly not a loss. But, still, Cabo Pulmo is a must on my next trip. I had hoped 2017 but looking to change jobs so maybe not.... sigh.
I love people, and really try to identify with their experiences. I like hearing spontaneous stories from other people, particularly something that affected them deeply. The emotion of the moment colors the words they'll use to describe the situation. 
