With the amount of air travel that goes on these days, I’m sure many of you have at least one insane story about how a trip took several times as long as it should have, or something terrible happened with your luggage, or you happened to suffer the most dramatic injury or illness you’ve ever had in your life while you were travelling.
Well, up until the last few years when visa restrictions prevented me from travelling, I was considered someone who traveled a fair bit, and to this day, my most insane travel story remains the one about that time it took me and my best friend 35 hours to fly from Toronto to New York City.
This is another one of my posts that’s pretty long, but so was the trip, so let’s call it art imitating life, shall we? Great!
Back in December of 2009, three years before I decided to move to Canada, I got on my very first flight from Australia to Canada and the USA.
It was a massive Christmas holiday trip that cost around $10000AUD (cannot IMAGINE spending that much on a trip these days!) and followed a typical itinerary for an Aussie going to the the USA for the first time: New York City, Las Vegas, San Francisco and Los Angeles (including Disneyland), but with an added twist – Toronto, Canada.
My dream trip
This trip was a huge deal for me. Not only was it the first time I was heading to my top bucket list destination, but it was also the first time I would ever see snow! But I was mostly looking forward to seeing New York for the first time, especially during the holidays. I would feel just like Kevin in Home Alone 2!
Why did we add Toronto to the trip? Because I had friends there, and since it was the Christmas holiday season, I was dying to see a white Christmas, and I was assured I would if we went there.
We had planned to be in Toronto until Dec 27th. After that we would head to NYC for four nights, one of which was New Year’s Eve, then we would cross over to the west coast and go from San Francisco to Vegas to LA, including a couple of nights in Anaheim so we could do Disneyland and be sufficiently thawed out by the time we got on the flight from LA back to Sydney.
It all sounds perfectly normal, and do-able right? Wrong.
Little did I know that flying around the Americas during the holiday season is a logistical nightmare at the best of times, let alone when your travel plans are disrupted.
And boy, did we have a disruption. On the last night we were supposed to be in Toronto, my travel buddy came down with a severe case of food poisoning.
The food poisoning
On Boxing Day we had gone up the CN Tower for the touristy thing and then taken in a decadent meal in the lower level restaurant. We all had the same thing, a burger, except for my travel buddy, who also ordered a Pina Colada. Well we don’t know if that’s what it was, but whatever she came down with had her vomiting every 20 minutes like clockwork for the next 24 hours.
She barely slept because she was throwing up all night, and the next morning we had to go to the airport to catch our flight, but she was in no condition to even get in a car let alone go through the airport process and get on a plane.
Cancelling our flights – BIG, but unavoidable MISTAKE
So we called the airline and cancelled the flights. “We’ll book on another one”, I assured her. I called our travel insurance company and told them what had happened and they said we could book another flight and they would pay “reasonable” costs – whatever that meant.
In case you weren’t aware, the flight time from Toronto to New York City is about an hour and a half.
Apparently watching Home Alone 1 & 2 five hundred times had taught me nothing, because of course, there wasn’t “another one” to book. At that time of year, you’re lucky if you find an empty seat on any flight.
But that particular year was even worse.
Explosive underwear: The almost terrorism
On Christmas Day of 2009, a passenger on a flight from Amsterdam to Detroit attempted a terrorist attack on board just before the flight landed in Detroit. He had a very odd plan that involved trying to light his underwear on fire.
Well, obviously this put the United States on extremely high alert and for however many days afterwards, passengers were required to present their carry-on luggage at security where it would be searched manually.
The endless delays at security
You think security is slow on a regular basis? Imagine how much longer it took now that the handful of security officers working were required to open and look through every single bag and scrutinize every item each passenger was carrying into the cabin. Now imagine this at during the holiday season when most flights are at capacity. The travelers in the security line were all sitting on the ground because it barely moved.
This obviously caused delays and disruptions, caused bags to miss flights, and what have you.
No seats available
It was during this time that we were trying to find two seats on a flight from Toronto to New York City.
We looked at every possible option. My Canadian friends suggested “flying from the island”. I pictured a sea plane teetering off a jetty or something insane, but my friends were referring to Porter Airlines, which had begun operating off the Toronto Islands at Billy Bishop Airport three years earlier.
I checked and not only was each one way trip like $1200 (which the insurance company did not approve) but at the time, Porter only accepted bookings under Canadian and US passports. (This has since been changed.) We scrapped that option.
We finally got seats
Countless Google searches and phone calls later (there was no Google flights back then!), we finally found the only two seats available going from Toronto to New York City.
The flight departed Toronto at 9pm and had an overnight layover in Montreal, with the second leg to New York departing at 6am.
We went through the insane security lines in Toronto, which my travel buddy had to keep ducking in and out of to throw up. We arrived in Montreal bleary-eyed and sleep-deprived. My poor friend looked like she was going to die.
Sleeping at the airport in Montreal
Of course, it wasn’t worth getting a hotel for 6 hours (and we didn’t think to anyway), so we slept at the airport on benches made of marble that were lined up beside the windows. Outside, it was around -20 degrees Celsius and the stone-cold benches were not kind to us.
The check-in kiosks mockingly declared, “This kiosk is currently closed. Please come back after 3:00 AM.”
Finally 3am rolled around and we took our bags to the counter.
And then we had ticketing problems
It was at this point that the check in agents discovered some sort of problem with our ticket, and somehow my travel buddy was cleared but I wasn’t.
At the time, I had no experience working for an airline so I had no idea what the issue was, or what they were talking about, so we waited helplessly while they figured it out. I can only assume the last minute booking wasn’t processed correctly and they were having issues with the ticketing or something.
The flight had also been delayed until 8am, so in actuality, we were lucky because it took them that long to figure out how to get my ticket to go through.
I don’t remember this clearly but my travel buddy made some sort of demand and they figured it out and we were on the flight.
We departed and were on our way to arrive at JFK by about 9:30 am.
The maintenance issue and turning back to Montreal
About halfway through the flight, we had a maintenance issue.
The flight attendant announced that we had a problem with one of the doors and we would be returning to Montreal.
Back in Montreal airport, we joined a long queue where one by one we were rebooked onto the “next available flight”. All around us people were making phone calls and speaking French which was kind of cool.
Getting rebooked via Cincinnati
Eventually it was our turn and we were advised that we had been booked on the next available flight, which departed at 4pm, made a stop-over in Cincinnati, and continued to New York, arriving at about 9pm.
Sleeping on the floor in Montreal again
Since we were already through security, there wasn’t much to do but hang out around the gates. So we set up camp and made Montreal airport our home for the next 6 hours. My travel buddy slept on the floor while I wandered around.
We finally got on the plane to Cincinnati, and after more security hell, boarded our last flight and made it to New York, where we had to go through US Customs.
Almost getting refused entry at the border
At that point we were so exhausted that we had barely any awareness of where we were or what we were doing.
The customs officer at JFK began the standard port of entry script, asking, “So why are you travelling to the United States?” Without even pausing I exclaimed, “Because we’re insane!”
My friend gasped and quickly explained that we were on holidays and we’d had a rough time crossing the border from Toronto and I was only kidding.
We are so lucky that he had a sense of humour, or at least understood the blunt Aussie one, not to mention knew what travelers had been through the past few days, because that could have gone a whole lot differently.
We finally arrived
We finally checked in to our hotel, which was near Macy’s, on December 29th at around 1am, almost 40 hours after we had left Toronto. We told the concierge about our travel ordeal and she said, “Wow. You’re lucky your luggage made it with you.”
Not sure I’ve ever heard a truer statement. How on earth did our bags make it through all that? Props to the ground staff that worked all those flights!
We missed two of our five days in New York, and we weren’t sure we’d ever have the opportunity to travel there again.
Remember, this was a time before social media was that big. You didn’t know what to expect then as much as you do now because you couldn’t readily find the answer from the 500K people that had gone before you and posted about it on social media. If this same situation happened today, maybe the outcome may have been different.
It also wasn’t that common to take long trips like this on a regular basis. It was more a once in a very long time thing, so we realistically may not have been able to try and come back to New York again to make up for the time we missed.
A lot of people who hear this story respond with, “Wow. It would have been quicker to drive.”
Yes. Yes it would have!
So next time you have a travel disruption, think of me and my 35 hour journey from Toronto to New York City.
Oh, by the way, it didn’t snow in Toronto that Christmas. It was one of the greenest Christmases they’d had in a long time. I also learned that Toronto doesn’t get that much snow compared to surrounding areas! New York often gets more than Toronto does apparently. It certainly did that year!
Luckily, I’ve lived here long enough that I’ve now had three white Christmases and that craving has been sufficiently satisfied. Now if only winter would end in January…
What was your craziest travel experience? Let me know in the comments!