Before Cancún, there was Stamford

Brett Freeman

The hardest part of our trip was leaving America

There is nothing like planning a relaxing family vacation to remind you how much work it takes to relax.

My wife and I had not traveled outside the country in about 15 years. Our passports had expired about five years earlier. There was also one small complication: I could not find them.

Apparently if passports are less than 15 years old, you can use the old expired ones as part of the renewal process. After 15 years, you have to apply as if you are getting a new passport. We were just on the cusp.

I would like to blame an intruder who broke into our house and stole nothing except two expired passports. The more likely explanation is that they disappeared somewhere inside one of my poorly organized filing cabinets.

There is also a very real possibility that, during one of my occasional bursts of organizational enthusiasm, I saw that they were expired and shredded them, not realizing that they can be used for renewal at a much lower price. I may have destroyed the very documents I would later need to prove that I once possessed them.

The State Department's passport website is akin to a "Choose Your Own Adventure."

• Were your passports issued over 15 years ago?

No. We received them precisely 14 years and 11 months ago.

• Were your passports lost or stolen? If so, you need to file a police report.

Crap. OK, so I go to file an official report. But before I get to the end of the form, it said that if your passports were expired, you don't need to file a report. Instead, proceed to the application form for new passports.

On the application for new passports, it makes you affirm that this is your first passport. Ummm... OK...

I filled out the forms, printed them and assumed — always a dangerous moment — that I had followed the instructions correctly.

We had booked our Aug. 9 trip only about a month earlier. By then, mailing the passport applications felt risky. Even expedited processing left little room for delay.

The other option was an urgent-travel appointment at a passport agency. But there is a catch: you must be traveling within 14 days, and you must bring proof of that travel. That means you spend the weeks before the eligibility window knowing you need an appointment but unable to secure one under the rules. Then the window opens and you discover that thousands of other procrastinators have been waiting for the same starting gun.

I briefly wondered whether more enterprising travelers had found a way to game the online appointment calendar (you can pretend you are traveling within two weeks to enter the website appointment calendar, and then you just have to secure an appointment within the two-week travel window). But I did not want to arrive at the agency only to learn that the State Department’s computer was smarter than I had hoped.

So I followed the rules and entered the website on the morning of July 26 (exactly two weeks before travel), and secured the earliest appointment available: an 8 a.m. appointment for Monday, Aug. 3, at the Connecticut Passport Agency in Stamford.

That morning, a thunderstorm rolled through Stamford. The parking situation was atrocious, the entrance was not obvious and I was clutching our application papers against my chest, trying to keep our family vacation from dissolving in the rain.

Despite the lightning, we were not initially allowed into the building. When the doors finally opened, a security officer barked for everyone with an 8 a.m. appointment to enter and form a single-file line. Anyone with an 8:15 appointment, we were warned, would be removed.

Once inside, we received the rest of the briefing: no cellphones, no ringers, no knives, no marijuana and no vaping devices.

I understand the need for security. I understand that employees who deal with the public all day encounter people who do not listen, do not prepare and occasionally attempt to bring astonishing things into federal buildings.

Still, there is a way to speak to citizens without making them feel as though they have arrived for intake at the county jail.

In my business, if we greeted prospective customers by barking orders and treating every question as an inconvenience, we would soon have fewer customers. Government has the considerable advantage of knowing its customers cannot take their passport business elsewhere.

The number of security officers also caught my attention.

I do not want any government worker to be unsafe, and I recognize that federal security decisions are not directly comparable to local school budgets. But the optics were jarring. Communities routinely agonize over whether they can afford a single school resource officer to help protect a few buildings containing hundreds if not thousands of children. At a small regional federal passport office, meanwhile, the security presence seemed almost to match the number of employees serving the public.

Perhaps there are good reasons for that. But government budgeting is ultimately a statement of priorities, and sometimes citizens are entitled to wonder whether those priorities are in the right order.

Then came the line.

One employee told us that because all three of us (my wife and son included) were applying, all three of us had to remain together. Near the front, another instructed us that only one person should approach the window. A third employee corrected him and said all three of us needed to be together.

At the counter, we learned that the forms I had completed after following the website’s trail (the online form automatically marked that this was our first passport) were not quite right. I explained that the website had led me there. The employee was unimpressed.

“I’m telling you to do it differently,” he said.

Fair enough. At that point he could have told me to recite the Pledge of Allegiance backward while standing on one foot, and I would have obliged.

Thankfully, he permitted us to cross out answers, add explanations and then sign. I have an embarrassing reaction when I become nervous or emotional: my hand shakes. And then I began to worry that the State Department agent would see my hand shaking and think I was some sort of threat. So, my hand started shaking even more. My hand was shaking so much that at this point, I was worried the guy behind the desk was going to call ICE to interrogate me.

But we survived. The applications were accepted. We were offered the option of expedited mailing or returning to Stamford to pick up the passports that Wednesday.

After everything we had experienced, there was no chance I was entrusting the final handoff to the mail. Lauren returned to Stamford Wednesday and collected them.

The passports were in hand. The vacation was saved.

All we had to do now was get to Mexico.

For all the warnings Americans hear about cartels and crime in Mexico, the most dangerous moment of our entire vacation may have occurred between our house and JFK Airport.

At about 2 a.m. on the morning of our flight, we were heading south on the Hutchinson River Parkway when a motorcycle passed us traveling north — in our southbound lane.

Seconds before, it caused an accident with the car in front of us. Fortunately, the people in the car appeared to be all right. We called 911 to report the whole situation.

JFK did not improve the situation. The approach roads were an obstacle course of potholes, barriers and narrow lanes. This is one of the great gateways to the United States, yet parts of the drive looked neglected enough that it should embarrass a country that regards itself as the most powerful nation on earth. There is no excuse. New Yorkers should be embarrassed by this. Mayor Mamdani should stop promising discounted groceries and fix those damn roads.

Inside, the kiosk repeatedly cut our printed boarding passes in the wrong place. I finally surrendered and downloaded them to my phone. Even though it was only 3 a.m., the terminal was a madhouse and the TSA experience is never pleasant.

Then we landed in Cancún.

The airport was bright, attractive and orderly. The immigration officer was friendly. The customs employees were welcoming. The shuttle representative was helpful. The driver seemed genuinely pleased that we had come.

Yes, the arrivals area included an army of salespeople, each appearing to earn a commission and each warning us that everyone else was merely trying to scam us. My first mistake in Mexico was believing that the first “official” person who approached us was, in fact, official.

But once we found the actual JetBlue Vacations representative, everything went smoothly.

I do not pretend that one airport visit proves anything sweeping about either nation. There are wonderful government employees in America and rude people in every country. But the contrast was hard to miss.

America had made us feel like a problem to be processed.

Mexico made us feel like guests.

And our vacation had finally begun.