Disclaimer: I don’t recommend that you do this.

The biggest challenge of my entire Europe trip faced me before I even stepped foot on the continent. To make it to Europe I had to make it through the US border first.

Simple right? Get a visa, don’t piss anyone off and you’re through. Not in my case. For the duration of my exchange I was fuelling my American adventures with an ESTA: It’s a $15 online Visa that you can get in minutes and allows you 90 consecutive days in the United States at a time for two years, resetting every time you leave the US. But there’s a catch – America, in its infinite wisdom also counts Canada, Mexico and all of the Caribbean islands as part of the United States. So even though I spent the overwhelming majority of my time in Canada, all of that still counted towards my ESTA’s 90 days. When I flew out of New York to Canada my 90 days had reset as I went through international, but it started counting again when I returned for a ski trip a little over a month later.

That 90 days ran out on the 30th of April.

My flight to Europe was on the 2nd of May. Out of Boston, Massachusetts.

I see a problem here.

I bought that flight because it was the cheapest flight to Europe from North America – Boston to Lisbon for $300. Far cheaper than flying straight out of Montréal. A $50 overnight bus for a huge saving. I figured since I’m entering the States only to fly out immediately there shouldn’t be too much of an issue. Now I just had to see if I was right.

I was a little nervous in the days leading up to my departure and considered buying an all-new ESTA altogether, but instead decided to give the border guys a call to see if it was okay.

After locating the exact border station I gave them a ring. The guy who picked up was super friendly, I explained the whole situation and he said that since it’s a “significant departure”, I just have bring all the documentation I can find and it should be okay. I made sure I did. I wanted to make this as smooth as possible. I thought about shaving my beard off as well – but considering that there is going to be an issue no matter what I don’t think it’d make much of a difference. Here we go.

The bus came into the small border station at midnight, and I had my laptop case filled with documents at the ready. My heart started racing as the nerves kicked in, but I tried my best to keep a calm and collected shell. As they did with all foreigners they took me around the back and I anxiously waited in line behind the others.

It soon got to be my turn and I handed the Border officer my passport. As he was searching for my visa waiver I decided to acknowledge the issue up front, and began explaining to the man that I called them earlier and was told that because it was a significant departure it would be fine, to which he lurched forward, slammed his hands onto the desk, looked me dead in the eye and said

“Don’t you dare tell me what a significant departure is.”

Whoa, buddy.

The guy told me that I violated the conditions of the Visa waiver program and shouldn’t be allowed into the country. He was furious.

From there he proceeded to grill the hell out of me. Mad with power, he interrogated me about everything, from going through every single stamp on my passport, making me admit I went to Cuba for spring break, demanding proof that I was actually in Canada most of the time (my acceptance letter which I had left in my laptop case by accident – what luck), to asking for my flight ticket out of America, and even going to the extent of asking to see the credit card I used to pay for the flight ticket – which was my friend’s card. I didn’t have enough money on my card at the time and prices were going up. Awkward. After telling the officer that he responded “So your friend just lent you $300 for a flight to Europe?” to which I said “Yep!.. And there’s literally no way I can prove it to you.” It took literally every ounce of my being to remain calm and composed throughout this whole thing. My heart was pounding.

The bus route stopped first at the Boston bus depot and then the airport, so the officer made me promise him that I would go straight to the airport and get off American soil as soon as possible.

“Do you promise you’ll go straight to the airport?”


“You’re sure?”

“Yes I promise I’ll get off the bus directly at the airport and board my flight.”


“I promise. I just want to get to Europe.”

He left for a minute, but it felt like an eternity. He comes back.

Stamps passport

I didn’t get off at the airport. I got off at the bus depot and chilled in a café and Boston Common all day. I’m such a rebel.

One thing he did tell me when he gave me my new Visa waiver was that I had to surrender it to the TSA/Customs Officers as I went through security, or I might get removed from the Visa waiver program. And… I forgot to. Didn’t really think much of it then but the uncertainty made for a little bit of stress later on.

And that’s how I made it through the US border on an expired Visa waiver – and I didn’t even need to shave! The hardest part of my Europe adventure was now over. I’m coming for you Europe.

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