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

Having the flight from our home city to catch the flight from Pittsburg to Orlando cancelled an hour before take off due to 'weather' (there was no issue with the weather). Having to drive to Pittsburgh, and then finding out that our connecting flight had taken off 5 minutes earlier. They made it up to us by flying us first class, but it was a stressful start to what would be my husbands first trip to WDW.
 
Microsoft melting down when I was over the Atlantic on my way to see 2 days of the Tour de France and having to spend $700 to get there to not miss BOTH days of the Tour, only one :(
 
My grandmother passed away on the first night of a 2 week trip to the Outer Banks (she was with us). Whole family was gathering there anyway, so it turned into a long family getaway/wake which my grandmother would have loved. Medical Examiner arranged for us to have her cremated and she spent the second half of the vacation on the dining room table overlooking the Atlantic!
1 year later we all took another trip to the BVI's to "bury" her ashes where my grandfather and great-grandparent's are. Another party she'd have fully approved of!
 

Flying from NY to Barcelona.....plane getting an hour out, turning around and going back for a part replacement. Sitting on tarmac for 4 hours and arriving too late in Barcelona to do anything before the cruise ship left.
Waste of Hop on Hop Off tickets.
 
Before we learned you don't fly into a cruise on the day of the cruise, we flew down to Ft Lauderdale the day of a cruise only to find out our check luggage did not fly with us.

The luggage didn't catch up to us until the 4th night of a 7 night cruise. Cruising with just the clothes on your back is not nearly as fun as cruising with all your stuff.
 
Arriving on the Outer Banks for a week after picking up the kids from camp. We walked in to find a message from my sister in law telling us the AC was broken at our house, the dogs were miserable and the dog/house sitter would be back when there was AC. After having driven 5 hours to camp, another 2 1/2 to the beach, I got back in the car and drove 6 hours back home. Slept, got the AC fixed and went back...to find that there was a mandatory hurricane evacuation! The vacation that wasn't!
 
It would have to be when we went to Hawaii for my sister's wedding. We were all going - my parents, grandparents, family friend - all together. We had a very early flight out to Dallas, where we would connect for Hawaii. We were delayed a little, so that conenction was tight! We did make it though - whew! But as we are going, halfway across the water we actually here the old, "If there is a doctor or nurse on board the aircraft, please identify yourself to a member of the flight crew." Yup, that's real! Okay, someone was having some issues. We had to turn back to San Diego, where paramedics boarded the plane and removed the person in distress. Nobody was super happy about it, but, okay, medical emergencies happen.

However there had been another issue on this flight - one of the lavatories was out of service. As we made our way back out over the Pacific, they had closed all lavatories on one side of the aircraft - then the other. There was a widespread issue with the septic system. Apparently, they legally can't fly without a working restroom. They needed to turn us around to a maintenance hub in LA! 😮 Again, we're heading back to the mainland. If you had taken a poll, we'd have voted tht we could hold it, but they needed the plane to be somewhere it could be fixed. At this point it's already like midnight home-time and we've got to the airport at liek 5 AM. Here's where it gets really bad though. They took all the passengers off that 747 widebody aircraft with plenty of extra space and crammed us into a 737!

So, we're finally on our way again - we don't get to HAwaii until like 1 AM local time, which is like 5 AM home time, almost 24 hours of travel! We were amazingly still able to pick up our rental car, but we are all tired and crabby. We drove to the wrong hotel, then had to find the right one. I thought I was going to die! The next day we spent in Honolulu so my sister could do some shopping for the wedding. It's just a big, dirty city and we were all pretty snippy with each other. It was a rough start, but things did get better once we got over to Kauai, which really is a paradise. Once we could relax, things went much better, but man, it was the trip from hell!
 
Arriving at OKW 2 BR to find ants all over the kitchen and water dripping onto the primary bath's sink from the toilet above. It took all afternoon and visits from engineers and others, scratching their heads like they had never seen issues like this. FINALLY, they found us another OKW 2 BR and helped us move. We tipped bell services (not their fault), so it did cost out of pocket. I must say that DVC did finally do us right as we were able to book a future stay at BLT in a 2 BR Theme Park View. It is just not how you want to start your first day of vacation!
 
DH left his passport at home thinking the id card was enough for a cruise. Luckily he told me when we were an hour away so we could go back. Losing that time was a bit rough though.
 
I have had a couple of rough starts over the years.

In 2011 We were heading to Disney and a couple days before we left my refrigerator died. There was also an issue with my car, the brakes I think and we were driving. Then I got really sick and we spent over an hour at South of the Border before I could risk going further. We did dig out the Pepto and I chugged that most of the way down after that.

The following year I came downstairs to a dead opossum on my new couch. My dog didn't like opossums for some reason.

Last September I took a trip with my granddaughter. Somehow I lost my driver's license between the airport at home and Pop Century. I was in severe panic mode as I needed it to get home again. The CM's at Pop were awesome and gave me several suggestions on what to do including have my passport sent to the resort. It cost me $60 to FedEx my passport to the resort but I was so relieved when it arrived only to realize my husband gave my daughter the EXPIRED passport. Thankfully that was OK to use since I had to get my granddaughter back home. She missed a week of school for the trip and couldn't afford to miss anymore.
 
Flew from Boston to Honolulu direct during COVID with masks. My daughter got motion sickness as we were landing and threw up all over my feet (in sandals) on the jet bridge. We had been sitting right near the door and were the first people off the plane so I stood there helpless as she just kept going and the entire plane of people walked past us, mortified.
 
Are we the only ones who've gotten only as far as the airport? It's happened twice that we've had our initial flight delayed/cancelled and we didn't get to our vacation destination until 2 days later. Most recently was Hurricane Milton, when Orlando Airport closed. Before that we got on the plane, then off the plane, then delayed several times before our cancellation/2 day delay.
 
I have a few.

We were heading to a 3 night music fest when the water pump in my Blazer went. Had to have it towed to a mechanic and spent the first camping night at a LaQuinta.

Our flight to Vegas was cancelled due to a hurricane so we booked one a day earlier to LA to rent a car and drive. That flight ended up being delayed 4.5 hours. By the time we got to LA, got our luggage that was delayed over an hour, got our car that took well over an hour, got checked in to the hotel that took us forever to find, we got to sleep for 3 hours, then drive 4 hours across the dessert. Well it should have been 4 hours but since we were both half asleep we kept stopping so it actually took closer to 6. I won $k on that trip though so it wasn't all bad.

We stayed at a REALLY crappy hotel in Tampa for a Busch Gardens / visiting friends trip and on the first night, the hotel caught on fire at 3 AM. We were evacuated. We ended up sleeping in our car for a night and got another hotel.

At breakfast on the first day a Lego Land trip my youngest threw up all over herself at Golden Coral. It's our fault for eating at Golden Coral.

My oldest started puking in the parking lot at MK. She felt better for a while, but 3 days later heading home she started throwing up in the car, all over the back of my head. Not a fun ride home.
 
First DCL cruise, airline cancels the DIRECT flight 30 min before supposed to leave, told us it would take 2 days to get to MCO. I went out of security to the actual ticket counter and built a flight with the one helpful person that works for Delta. Well a flight from Arkansas to Salt Lake City to MCO, we arrived at 3 AM got to the hotel at WDW at about 4:30, slept until 8 and then got on the bus to the ship. Terrible start, but we didn't miss the ship!
 
We were headed on a two-destination trip: NOLA to visit my sister and brother-in-law for a few days, then over to MCO where we'd visit a friend in Cocoa Beach (who was terminally ill), do 2 days at Disney with another friend (who I met here on the boards!), and then a visit to my BIL/SIL (he'd just been declared cancer free) near Tampa. We had a crack-of-dawn flight out of an airport that is 2 hours from home so we were going to drive down the day before our flight and stay over. DH and I were packing, clothes laid out on the bed, when the phone rang. It was DD: "Mom, feel awful and have a fever of 101 and will you take me to the doctor?" Yes, it was January of 2021, and it turned out DD had covid. I sat in the tiny Kia Soul with her for 4 hours until it was her turn to see a doc, so we knew I'd been exposed and decided we couldn't take our changes. We canceled everything. Fortunately we were flying on points with Southwest, so I got those back. Disney was great about canceling our hotel, gratis, but we had 2 day park hoppers that we oculdn't get refunded (held value until our May 2025 trip, but we had to pay more for the same tickets by then). I don't think we lost out on much- they even let us cancel the hotel room booked for that night before flying- but man, were we disappointed.
 















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