Anguilla: Dumb travel mistakes we made (so you don't have to)

Updated: Aug 23

Sometimes dumb travel mistakes start at home. This was the case for our trip to Anguilla.

Somehow what started as a one-time special trip for Joe's 50th birthday has turned into an annual custom: the birthday surprise destination. This particular year I decided that our celebration should be filled with sun and sand, so I planned a trip to the island of Anguilla, in the British West Indies.


I always start to pack about a week in advance of a trip, not because I require all sorts of special planning but because it's so exciting and I can't wait to go away! This trip was no different, and in the days leading up to our departure I started piling up the items I was going to be packing. One of the first items I always put into my pile: my passport.


We were leaving on a very early morning flight, so the night before I made sure everything was in my suitcase and my carry-on to minimize any last minute scrambling. In fact, the next morning, I had plenty of time to kill before our Uber was scheduled to show up. I brought my suitcase and carry-on downstairs and was ready to go as soon as the car arrived. And then it happened...I couldn't find my passport.


Now, I knew I'd had it in my pile. I could see it right there on top, in my mind. With twenty minutes still to go before our ride arrived, I methodically went through my suitcase thinking that maybe I'd packed it in there by mistake. Nope. So I went through every corner of my carry-on. No luck. Now I was starting to get concerned.


Joe was done packing and the car would be there in a few minutes. So things got frenzied. And gross. "Maybe you threw it out by mistake," Joe offered. I was pretty sure I didn't, but that didn't stop me. I rolled up my sleeves and started digging. Piece by gross piece. Both in the trash can in the kitchen and the one in the garage...with the bag of old, discarded food. This was a long-shot because I just knew I didn't throw it out. Of course, it wasn't there, but I did get to relive the previous week's rotting food.


At this point Joe was watching the car on the Uber app crawl closer and closer.


Now I was freaking out. And Joe joined the search. We looked under the bed, behind the dresser, pretty much anywhere in the entire house I could have put my passport. And it was nowhere. I went from freaked out to...well, freaking crazed!

When the Uber reached the end of our street, I made a decision: Joe would go to the airport without me, and I'd drive to meet him when (if?) I found my passport. I handed him the printed itinerary I'd written for our trip, and said, "Surprise! We're going to Anguilla! And, surprise, you're going alone!" He kept asking if I was sure I wanted him to go without me, and I was. If I missed the plane, I'd find another flight and meet him there...eventually. And he shouldn't suffer for my dumb mistake.


Our flight was leaving in just over an hour and a half. It would take me at least 40 minutes to drive to the airport if I found my passport in the next five minutes. I'd just make our flight.


Only, I wouldn't. After looking everywhere, I finally gave up searching for my passport and resigned myself to the fact that Joe would be taking off into the air without me. It was time for the contingency plan. I removed my laptop from my carry-on and powered it on to look for alternative flights as I stood at the kitchen counter. Of course, there were no more flights that day.


Completely deflated (to put it kindly, more like ready to burst into tears), I took a deep breath and pulled out a chair at the kitchen table to figure out when I could join Joe.

And there it was. My passport. On the chair. It must have slipped off the table and landed on the seat when I brought my carry-on downstairs. All of sudden I was off and running again. I grabbed my bags and jumped in the car. I had just over an hour to get to the airport and make the flight. There shouldn't be traffic at 6am, so I would be golden.


Except, yes, there was traffic. This is Boston!!!! I called Joe from the car going 5mph behind a never-ending row of practically-parked cars and told him I was going to get there if I had to get out and run! I put every positive vibe in my body out to the universe to make the flight, but it sure wasn't looking good.


Finally, with 15 minutes to go, I pulled my car into a parking space in the airport parking lot and ran, like I've never run before, to the terminal. I begged the woman at the desk to let me try to catch the flight and, because I wasn't checking a bag, they said yes. I had less than five minutes to make it through security and to my gate. I cruised through the empty TSA pre-check line and bolted toward my gate yelling, "I'm here!! I'm here!! Don't close the gate!!"

Finally, up ahead, I could see the agents standing at the gate ready to close the door. Again, the kindness of the gate agents was amazing, and they held it until I arrived, panting, with my boarding pass. I rushed onto the plane and down the aisle past all the seated passengers until I spotted Joe and raised my hands in victory!! Let the birthday celebration begin!!


The lesson here? Treat your passport like the Wonka golden ticket. When packing for a trip, your passport is job number one. Always put it somewhere safe and sound the night before your trip. And also hope that your sweet, friendly flying-solo husband freaks out the woman sitting next to him by starting a conversation with, "You look like you're traveling alone...me too." That way, when you do finally arrive after a mad dash to make your flight, she is only too happy to switch seats with you so you can travel together after a horrible morning you never want to experience again.

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