Tuesday, January 10 – transit from Madison to Toronto

Welcome back everyone! Thanks for following along as I begin Winter Escape #4. This will be my first travel outside of the United States since I exited Argentina in March of 2020 at the beginning of the Covid shutdowns (thanks again for the heads-up Kait!). The plan this year is to start out in Central America (Panama), then dip into South America (Colombia), and conclude by working my way north through the Caribbean. I’m hoping to visit at least 12 countries or territories over a period of 3 months or so. Kind of ambitious, I know, but I’m not getting any younger! (And to be honest, I have a goal of visiting 100 countries in my lifetime, and this is an easy way to cherry-pick a few. I currently sit at 70.)

My trip to Panama will include an overnight connection in Toronto via Air Canada. I booked through AC because I have a credit from them due to their cancellation of my return flight from Buenos Aries in 2020 (the credit expires in March of this year). Taking into account the credit, the net cost of my one-way ticket to Panama City was $61. (Seems high, right? Inflation I guess)

I’m starting off by taking the bus from Madison to O’Hare (thanks for the ride to the Lake Street stop Chuck!). The trip takes about 3 hours and costs $36. Fortunately, my flight doesn’t depart until 3:30pm, so I don’t have to leave on a super early bus from Madison. Unfortunately, the 6pm arrival in Toronto means I’ll have a 14+ hour layover until my flight to Panama City leaves at 8:30 tomorrow morning. And I don’t plan on spending it at the airport! So I booked a hotel close by for $125.

The bus ride goes as planned, arriving at O’Hare around 1pm, well in advance of my flight (which, as you will soon learn, becomes critical).

I’ll lead off this part of the story by saying that I tried to check in for my flights a few times online since the opening of the 24-hour window. All to no avail though, due to a generic error message. I wasn’t too worried however, because my booking was confirmed. I even had seat assignments. I figured it was just some glitch in the Air Canada system. So, when I got to the airport I also tried to check-in at the kiosk. Still no luck. Next stop, a visit with the ticket agent. And this is when I’m told that I will not be allowed to check in for the flight. Wait, WHAT??? The reason given is because I only booked a one-way flight; a return is also required. I explained my plans to the agent (visiting multiple locations over 3 months, next stop is Colombia, no set return date, etc.), and she seemed agreeable to let me check-in. However, she needed to run it by her supervisor, who was adamantly opposed. Ugh!

The friendly agent suggested I just buy a cheap return ticket for some date in the future. I agreed that that would be my best, and likely only, option. But before I went away to search on my phone for a ticket, I wanted to have a talk with the supervisor. My point of contention was the timing in which I was informed of my no-travel status. Obviously the system had flagged my reservation early, hence the error message when I tried to check-in. Why was I only informed of this issue at the last minute, when there was very little time to correct things? Her only response was that “the entry requirements of the country being visited are the responsibility of the passenger”. Mmmmm…

So as I contemplated how I should go about booking this return flight (make it changeable so I can actually use it when I return to the States; make it fully refundable; go with a low-fare carrier and just eat the cost, etc.), Then I remembered that U.S. airlines provide full refunds on bookings that are cancelled within 24 hours of purchase. Problem solved! I ended up buying a one-way ticket on American for $280, going from Panama City to Miami in March.

This task complete, I went back to the ticket counter and showed (the same) agent my confirmed booking and was good-to-go. She was really nice about it, saying she would have let me go if her supervisor wasn’t around. She even gave me some suggestions about what to see in Columbia, where her boyfriend is from.

Upon my arrival at the Toronto airport hotel, I went to work on a few things:

• Review the Panama entry requirements. It turns out having a return or onward ticket is one of the criteria for entry. That’s on me for ignoring it. What stood out in my case though was the onward part; a ticket to Colombia would suit me just as well as one to the States.
• Cancel my American reservation. Full refund please!
• Book a flight from Panama City to Bogota, in case Panama immigration asks. I had already reserved my hotel in Panama through the 18th, so I booked a one-way departure flight on that date for $154.

Wow! This was kind of a long narrative. Sorry about that, but it was an eventful day!

Wednesday, January 11 – Transit from Toronto to Panama City

The flight to Panama City was on an Airbus plane similar in size to a 737, and was pretty full, but luckily I had a empty middle seat next to me. The flight took about 5 hours, arriving around 1:40pm (they’re on US Eastern time).

The line for immigration was fairly short, and I made it through in no time. In case you’re wondering…NO, the officer did NOT ask me anything about a return or onward flight!

(I have a theory about this (probably obvious to most other folks!). I think the airlines and immigration agencies work together on enforcing some of these entry rules. The airlines are the first point of contact, so are in the best position to confirm if a passenger has the proper passport, visa, and flight requirements. That way a passenger doesn’t make the journey to another country and is ultimately turned back. In fact, I faintly recall going through a similar situation in the past (memory issues!), where a ticket agent informed me that airlines can be fined if they allow a passenger with improper credentials to board an international flight)

I reserved my hotel via Booking.com, and as a promotion they offered a free car service ride from the airport. Nice! That was worth around $30.

I was going to roam around the neighborhood a little bit this evening, but I was beat. I have many days ahead of me on this trip, no need to rush it!