Cross-Border Travel

Recapping a laughable travel experience from NYC to Kelowna and back

From September 9th through 13th, I was fortunate enough to fly across the continent to meet my golf buddies in Kelowna, BC for a five round, four night extravaganza. The trip was phenomenal and a full recap of my birdies, laughs and pictures will be coming in the future.

The purpose of this post is to provide a detailed description of the travel experience itself, since most people haven’t flown across the border much and since I found the relentless run of seemingly non-sensical events quite humorous. Keep in mind, I travel a fairly decent amount, so typical delays, lost baggage, etc. isn’t super uncommon.


New York to Kelowna is not an easy trip. Cross border, 3-hour time difference, and a tiny destination airport are all working against you. I booked the round-trip flight shortly after hearing about the trip from my friends, and used Delta reward miles to pay for it. Joke #1: This was a SkyMiles reward trip

Since I started traveling as a consultant, I’ve been very loyal to Delta and feel strongly that they are the best airline in the US. I’ve had nothing but good customer experiences with them, and when I need to get in touch via phone, the agents are always super helpful and their technology is top-drawer.

Quick sidebar: The only time I’ve had an issue up until this trip was when I booked a flight from NYC to Toronto back in November. Since WestJet handles the Canada-bound flight (through a ‘partnership’ with Delta), I wasn’t receiving any change notifications through my Delta app. The night before my flight, I realized I didn’t have a WestJet confirmation number to check-in so I called Delta who informed me that WestJet had cancelled my short flight from NYC to Toronto and re-booked me New York → Detroit → Toronto.

Because of this previous experience with WestJet operating the flights, I called to get my WestJet confirmation a few days in advance this time. Sadly, I found out that once again, they had basically changed flights out of the blue. I’ll do my best to describe below.

Original Outbound Scheduled for 9/9: NYC -→ Toronto → Kelowna

Updated on 9/6: NYC → Nashville → Toronto → Kelowna (NYC → Toronto cancelled)

Aside from this update being geographically absurd, the flight wouldn’t have even arrived in Toronto on time to catch the flight over to Kelowna so it was essentially a glitch in the re-booking software after they just decided to cancel the NYC to Toronto leg.

This prompted another hour-long call with a Delta rep who was nothing but helpful, pulling down every possible permutation to get my to Kelowna on time ahead of our 3:45pm tee time on day one.

He booked me two outbound itineraries:

Option 1: Keep the Toronto → Kelowna leg and I find my own way to Toronto

Option 2: Leave NYC one day early and fly NYC → Minneapolis → Calgary, overnight in Calgary, then take Calgary → Kelowna on 9/9.

Unfortunately, having just come back from my Winnipeg vacation, knocking off work an extra half-day earlier than planned wasn’t in the cards. So I bit the bullet and booked an Air Canada one-way flight from NYC → Toronto on points to get there in time for the Toronto → Kelowna direct WestJet flight that I was still booked on.

Come travel day, I had no issues catching that Air Canada flight at 6:30am from La Guardia. Customs in Terminal 1 of Pearson Airport was relatively painless, and I shuffled over to Terminal 3 to go back through security to catch my direct to Kelowna. Once again, WestJet’s app is a joke and provides no solid push notifications for any changes. I get to the terminal and see my Toronto → Kelowna direct has been canceled. After checking in at a kiosk, they re-booked me on a Toronto → Calgary → Kelowna itinerary. This arrived 2 hours later than the direct intended to, which was still annoying but ended up getting me there in time to meet the guys, enjoy a Corona at the house, meet my golf clubs (thank god I didn’t have to travel with them as my friends brought them from Winnipeg), and enjoy the beginning of the trip.


Original Outbound Scheduled for 9/13: Kelowna-→ Toronto → NYC

Updated on 9/6: Kelowna → Calgary → Atlanta → NYC

This outrageous change in itinerary that I discovered before leaving on the trip was definitely frustrating because of the laughable route, but even more upsetting since it meant a 6:30am departure from Kelowna (rather than my original 10:30) after a 4-day exhausting golf trip.

However, I was fine with it, until I started to peel back the layers of the British Columbia Covid-19 Testing system. To cross into the US from Canada, you need a negative Covid test, regardless of your vaccine status, within 3 days of departing. Since I was scheduled to leave Monday, I figured I would go get a test on Saturday prior to our afternoon round. For context, to get a test in New York, I walk 200 meters to the end of my block, line up behind 2-10 people and get my test in 5 minutes our of a mobile testing truck.

In Kelowna, Google pointed me to two places. First, it was pretty explicit that for travel, you needed to use the test site at the airport. Makes sense. However, when I Googled this, I was greeted with these convenient hours:

Meaning this was out the window since it was Friday night when I looked this up and my flight was 6:30am Monday. Why have something essential to travelers open for hours that aren’t even close to travel hours? Seems comparable to the conundrum of hot dogs being sold in packs of 10 but buns being sold in packs of 8.

So it as on to option 2 for Covid Testing at Interior Health. Conveniently, this was only a 30 minute walk from our Airbnb on the Okanagan, so I went for a stroll Saturday morning. I was hoping to sneak in for a walk-up since the first available appointment online was at 2pm, but our tee time was 1:30pm. The guy at the door told me three key things:

  1. There are absolutely no walk-ups

  2. You can’t use this test for travel purposes (this made no sense to me, since any type of Covid test is fine to get into the US)

  3. Book an appointment online for later today

So, I booked online for 7pm (after golf) having full intentions to not mention travel to the nurses, and just claim I had symptoms. Already this is becoming more of a circus than I hoped.

After golf, my buddy Sean accompanied me, I got my test, everyone there was very nice, and they said “because you don’t have a BC health card, we can’t email or text you your results, you have to call this phone number”.

While that was annoying, it was understandable, and Lynn and I had to follow a similar process when we got our tests back in Manitoba.

Calling for Results

The next day, during our final 36-hole day, I kept calling for my results. However, there seemed to be no way I could access them. I never was able to speak to an actual human on the line, and all of the prompts said to just keep using the website or to enter a BC health card ID. The best part of the recording was the offer: “if you cannot access your results online, please call back”.

At this point, it’s Sunday at 2pm, I’m in the middle of our last round of golf, my flight leaves in 16 hours, and I’m starting to panic. My one saving grace was that the first leg of my flight was within Canada (Kelowna → Calgary) and I had heard there was some rapid testing available in Calgary airport. Since you don’t need a Covid test to travel within Canada, I thought I’d at least get to Calgary and then could figure it out. The real stress comes with my job - the fact that I’m not technically allowed to work outside the US border, so with important meetings scheduled for Tuesday morning, getting caught in Canada wasn’t really an option.

Return Day, 9/13:

I left our house around 4:30am with the other 7 guys still sleeping, and arrived at Kelowna airport about 2 hours before my departure. I jumped in line at the WestJet counter to get my boarding passes which they for some reason couldn’t issue via the app.

I spoke with the first agent who asked for my Covid test and ID. I explained to her that I hadn’t received my test results back, but that I just wanted to get to Calgary where I would get my test to go to the US. She said that she couldn’t check me in to the entire itinerary without the test results, regardless of the first destination. After thinking for a bit, she provided two solutions: wait here until the Covid test at the Kelowna airport opens (I had already researched and their first available appointment was 11am so that was out the window), or book a separate one-way ticket on the SAME FLIGHT flight (Kelowna to Calgary) which they could check me into without the test.

I didn’t pull the trigger yet because in my extremely tired state I was imagining there had to be another way. After doing more research, and knowing I’d never be able to get through to WestJet customer service, I bit the bullet. I got back in line, and the guy sadly took my credit card, charging $460 for a seat on the exact same flight that I already had a seat. The key to this plan, and I asked him 100 times, was that I could still check-in to the other two legs of my original itinerary (Calgary → Atlanta → NYC), and he assured me I could.

As soon as this was complete, I booked my Calgary airport Covid test (thanks Lynn) through a slick Calgary-based startup called Numi. Here was the scenario I was faced with:

  • My flight was scheduled to land in Calgary at 8:30am

  • I booked the Covid test for 8:45-9:00 (15-min windows they give you)

  • The antigen results were supposedly ready in 15 minutes (I had no evidence whether this was true or not while booking it from Kelowna)

  • My flight to Atlanta was leaving Calgary at 10:00am, meaning I still had to clear customs and security after receiving my results

Before leaving Kelowna, Lynn was an absolute trooper via text message, helping me with all the scheduling, researching other possible ways to get into the US (never mind New York), and generally keeping me sane before 6am PST.

One extra kick in the gut I received before leaving Kelowna: I was looking back through the Kelowna Covid testing website referenced above, and noticed that if you clicked beyond that main page, their hours actually showed that Saturday was an option, which would have saved lots of hassle, stress and money :(


My flight arrived from Kelowna about 10 minutes early - could my luck be turning? I sprinted through the terminal to find the Numi setup. It was a little confusing since I technically had an appointment, yet there were two different lineups, one to check-in at the desk and the other to wait to be called. After 8 minutes I got to the front of the line and checked in with the team. They were super friendly and asked what time my flight was. I said “sadly it’s in an hour,” to which she responded “man, you all seem to be cutting it close, you should get tested ahead of time” while smiling. I responded saying “I totally get it, and I did get tested, but I have no BC health card, and they never gave me my results!” She commiserated with me, explaining several other horror stories she heard about the lack of testing in BC and assured me that I’d have my results in time.

10 minutes later they called me, did the 4-second swab, and I had my printed results exactly 16 minutes later. I ran to the WestJet counter, wide-eyed thinking this could actually work.

There were zero customers there as I guess the Atlanta flight was all checked-in and there were no other International flights for a while. There was one gate agent left and before I could speak she said “sorry it’s way too late to check-in to the Atlanta flight, you’ll have to go over to domestic and they’ll rebook you”. I was deflated, but explained I was already checked in (not sure if that was true) and that I just got my Covid test results and had no bags (thanks Danny for taking my golf clubs home to Winnipeg). She checked the system, agreed that I had checked in (phew) and printed a boarding pass for me.

With my flight scheduled to depart in about 25 minutes, I sprinted to security (there was no line due to the lack of International flights) and sprinted through customs without any problem. I found my gate and arrived in time as there were still people boarding! Such a relief to know that I would at least get into the US, I’d at least be able to work, and the $460 to stay on my same flight and the $75 Covid test weren’t complete wastes of money.


Back in Delta’s home base, and feeling like I was in good hands, I had to walk for about 40 minutes upon arrival in Atlanta. The shuttle between terminals was under repair so it was a bit of a haul, but nothing I was worried about. Because of the weird handling of flights between WestJet and Delta, I was never able to get my boarding pass for Atlanta → NYC on my Delta app in my phone. Odd, but didn’t think it would be an issue.

When I got to the gate, I asked the agent if she could print my boarding pass (I saw in my app I had a seat, just now pass). She looked in the computer and was completely dumbfounded saying “this was WestJet booked and they never sent us the actual ticket number, which we need to print you a boarding pass. Can you call WestJet?”

I fully refused because I knew WestJet didn’t answer their phones so she begrudgingly called two different numbers with two different phones and sat on hold for the next 20 minutes as every other passenger boarded! I was so sure the final straw would be me not getting on a flight that I was standing outside of, knowing I had a seat assigned to me! But as the final passenger boarded, someone on the line picked up for her, transferred the ticket over and I was all set.

New York

The Uber ride from La Guardia to my Upper West Side apartment could not have been smoother. I walked in the apartment at 8:30pm ET, 13 hours after leaving our Kelowna Airbnb.

Thanks for reading, and thanks to everyone who helped out with encouraging text messages throughout the entire travel itinerary - I appreciate you!