The Lucky One

People tend to say things like, “One day I’m just going to pick a place on the map and jump on a plane.” I’m the kind of person keen on actually doing something like that — and luckily, the best job in the world now allows me to act on those desires.

In my short time as a flight attendant so far, and actually since I left my prior job in the media, I’ve had insane luck. (Turns out such luck comes with a price — more on that later) 

In early April, I was assigned a one-day trip with four legs — a pretty long day as far as my airline is concerned. When I reported to the airport, the first leg was cancelled, reducing me to only one working leg that day. Not bad, right? The airline deadheaded* my crew to New Orleans, scheduling us to head back on a working flight to Chicago that night. Welllll, that flight got cancelled, leaving us to have a grand ole time in Louisiana and deadhead back the next night … essentially a paid vacation. Again, not too shabby.

*A fancy word for when flight attendants and pilots sit as regular passengers on a flight but are still technically on duty. 

And it was a double whammy: That little excursion left me with a rearranged schedule that gave me eight (yes, eight!) days off in a row.

I couldn’t really just not go somewhere … so Kyle and I decided on the gorgeous getaway of San Juan, Puerto Rico! 

The trip didn’t involve a lot of planning, but does anything in my life? We decided to test out Airbnb for the first time — and let me tell you something: It’s my new favorite way to travel. A gracious, sweet man hosted us in a cute, one-bedroom/bathroom, private space just a short, sunny walk to the beach.


The water system in our temporary home seemed strangely wired as the lights flickered every time we turned on the faucet or shower … but if it’s up to me, I’ll trade a few gentle, mysterious shocks for an authentic experience any day.

We spent our first night in San Juan frolicking the beach, stuffing ourselves with delicious food and hanging with locals at a nearby bar with live Puerto Rican music.

“Where are you from? How did you find this place?” they asked.

It was so refreshing to meet the welcoming people of the place we were visiting as opposed to staying in an area where most interactions would be with other people on vacation.

The people of San Juan were some of the proudest, kindest souls I’ve met. They were so quick to tell us how happy they were to have us visit and experience the history and natural beauty of the area. We got suggestions on what to do with our next and only full day on the island before our drinks set in, making us ready to wander on the beach and head back to our cozy little place.

The next day, I slathered not enough sunscreen on my white-as-paper skin before heading out to explore Old San Juan.


We walked and wandered around all day, taking in the beaches and sites and enjoying the warmth and sun that my skin would remind me of later in a big way. We toured Castillo de San Cristóbal and Castillo San Felipe del Morro, experiencing the highly sought after entrance to the New World firsthand.

Even the bathrooms in these places had breathtaking views of the ocean. I don’t care what anyone says — I don’t think I’ll ever stop being overwhelmed by the ocean. I’m thankful that Kyle likes to take pictures. I’ve always been terrible at remembering that, but it would admittedly suck pretty hard not to have any photos of this trip.

Later that night, we wandered through the colorful streets of the city, ate expensive Mofongo and fell asleep full and happy.


The following morning was already our go home day, which came far too soon! We had to get home (which almost didn’t happen), but there is so much to explore in San Juan and the surrounding area! You could spend weeks I’m sure and still not experience everything.

We spent that day swimming in the ocean once more, eating at a panadería, walking around and slurping some smoothies at a cute little juice place before heading to the airport.

The dreamlike state ended there when the customer service agent informed me that he didn’t think Kyle and I would be able to get on the flight back to Fort Lauderdale to connect to Chicago. If you didn’t know, most airlines offer their employees free standby travel, meaning you get on if there’s leftover seats. There usually are, but flights out of Puerto Rico are often full or overbooked (insert funny United meme here), I have now learned. I REALLY didn’t want to be responsible for Kyle not getting home in time for his work assignment.

But as I previously stated, my luck still has not run out. Just as I was about to promise the gate agent my firstborn child, we got the VERY LAST two seats on the airplane. Utter relief washed over me as I buckled in. Lucking out again, we made the connection back to Chicago later that night. Overall, we only paid for our low-priced Airbnb, food, drinks and touristy shenanigans! Pretty sweet.

BUT … PLOT TWIST! A trip to the lav on that last flight led to the discovery that my slightly burnt forehead was quickly swelling.

Great, I thought … what an adventure this will be.

It only proved to get more interesting the following day when I could barely open my left eye due to the swelling that had engulfed my entire eye area.

My scowering of the internet revealed that this was yet another new, interesting reaction to the almighty sun. My skin and the sun don’t really mesh. It didn’t hurt, which was awesome, but it looked wildly unsightly. I luckily (again) didn’t have to work for another couple of days — enough time to hunker down inside and allow the swelling to go down. If I had to work, I truly don’t know if my supervisors would have allowed the likes of me on the plane near the passengers.

I didn’t take any photos, which now I kind of regret. I was pretty girly about the whole thing and didn’t want anyone to see me in that sort of state, but the more reasonable part of me wishes I would have went out on the town to gauge the reactions of strangers and maybe make up a story about getting in a bar fight (and winning, of course).

Moral of the story: I need a big, floppy hat and liberal sunscreen reapplication. But, like I’ve reiterated many times now, my luck has been INSANE … I had to pay for it in some way. 😉 WORTH IT.

Overall, my first non-revenue travel experience (and first time traveling as part of a couple) was a smashing success! I look forward to many more adventures that hopefully involve more strokes of luck, authentic experiences and a non-bloated face.

Thanks for stopping by! Until next time …

Peace, love & fairy dust,

— YourKayla

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