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

Driving to Cape Cod with our 6 y/older and then 3 month old newborn for a monthlong vacation.
Newbie was using cloth diapers at the time but decided to switch to disposables for the duration. Stopped at a rest station to change his diaper. Oh dear Lord above his butt was fire engine red and he was obviously allergic to Pampers! Fortunately had a few cloth diapers with us and lined the disposable with one. Decided we’d buy some birdseye cotton or already made cloth diapers at a 5&10 cent store on the Cape.
Not one store still carried them nor a fabric store so every day my Mom and I took turns washing out the ones we had.
That baby mooned us a lot that trip.
 
We have had a number of them but my top two:

Scheduled dive trip on a liveaboard in Belize leaving in 2 days. Weather forecast decided snow in Atlanta the next day. We had not packed yet. I was at work when hubby called to tell me we had to find something out of Atlanta that day. I scrambled and found a flight from Atl to Dallas to Belize but it would be an overnight in Dallas. We could not reschedule the live aboard and like a cruise if you miss it you miss it. Got the flight booked and rushed home. We had about 4 hours to get to the airport from Athens to board the flight. I told hubby what to grab and he threw it all in the truck. I was in the back seat packing while he drove to the airport, one a good day you can make it in 2 hours on a bad 4. We made it in a hour and half. Got to Dallas with no hotel reservation. This was back before you could book anything over the internet with your phone. I called my office and had my co-worker look up hotels from the office and she found one in the airport. I called and got up a reservation. We arrived in Belize about 3 hours before time to board. Hubby did manage to get all the proper dive gear and thankfully since it was a live aboard we only needed a few bathing suits and t-shirts.

On a dive trip to Bonaire with a group, on the first dive of the first day. It was a shore dive and while walking in there was a lot of coral and rocks. I stubbed my big toe on a coral/rock and broke it. Finished the dive in pain and thought I just had a bad stub. Went to the grocery store with hubby, walking and standing and back to the room. It was obvious it was not good. Thankfully there was a doctor in the group. He came to the room and looked at it and said, yep, probably broke. Showed hubby how to tape it and what I should do to keep the swelling down a tad. Hubby had to go back to the store for tape and loads of OTC pain meds. I did every dive on the trip, 3 a day including one shore dive (where you walk in) and two boat dives (jump in ouch) every day except one. Hurt like heck but darn it, we paid for the trip and I love to dive so a broken toe wasn't stopping me. I even carried my own gear every day except one.

Bonus - 3 days before a trip to Little Cayman (dive trip) I sprained my ankle. Wasn't cancelling the trip, my adult son was coming with us and it was his first international dive trip. Hubby and son took turns wrapping it as tight as they could every day and I hobbled around as best I could in the airport leaning on my son. The only trip I've not carried my own gear since my son felt sorry for me and carried it. Our room was upstairs with no elevator. Good times.
 
In New York City about to get on a cruise when my husband - who came a couple of days to NY after me - realized he didn't pack his Passport. He suggests I just "go on the cruise without him" or perhaps he can fly home, get his passport, and then meet me at one of the ports....

We head to the cruise terminal to explore our options and fortunately he had his Global Entry card on him which was allowable for entry in to Canada so I didn't have to go on the cruise alone (which I was not going to do). But it was still a hassle at every port until a supervisor came to agree the Global Entry card was acceptable...
 












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