
I will be a person who fits everything into a carry-on.
I will intentionally select pieces that work together. There will be no misfit dress that requires its own pair of shoes. My crisp, white button-down will serve triple-duty: I’ll wear it on the plane, over my swimsuit, out to dinner with a pair of fun pants. I will only need one jacket, and it will somehow go with everything. For shoes, only three: A casual sandal. A sneaker. Something dressy.
I will know where everything lives in my large leather designer tote; my personal item that perches effortlessly atop my chic, hard-sided spinner bag. The tote inexplicably has no zipper, and I am unfazed because I would never over-stuff a tote bag, nor accidentally spill its contents. My passport sits in the purposefully designed pocket, as always. My laptop/Kindle/iPhone, all 100% charged, are nestled in their own compartments. My sunglasses rest inside their pouch to protect the lenses.
I will feel put together at the airport. Dressed in classic and comfortable slacks, and a stunning cashmere wrap slung over my shoulders, I look not just ready for a plane, but for a luncheon with someone who uses the term luncheon. I will not drip my Starbucks on my pristine white button down. I will open my laptop and work on the plane. I will deplane my flight looking dewey, fresh, and unwrinkled. I will fly with a jaunty straw hat on my head.
I will arrive at the hotel, and unpack immediately. Throughout the week, I place all worn clothing either back on the hanger, in a drawer, or in the linen laundering bag I always bring when traveling.
I will wake early and exercise at the hotel gym. I will pack multiple sports bras, leggings, and gym socks. I will spend an hour on a treadmill, or squatting heavy sets of 10 and perfecting my push-up technique. I will sign up for the poolside yoga class I read about online. I will come back from this trip stronger than ever.
I will test my sartorial limits. Though I only packed a handful of items, many of them will be devastatingly on-trend. I’ll walk through the streets of town looking like something out of Italian Vogue, donning a bright and trendy statement dress I’d never attempt back at home. I’ll finally figure out how to tie a scarf around my head in a way that looks chic. On this vacation, I will be a woman of effortless style.
I will eat a salad for lunch. I will stay hydrated. I will drink alcohol, but never to excess. I may indulge in a dessert or two, and it shall involve dark chocolate. I will get to bed at a reasonable hour (because sleep is good! Also, that morning workout in the hotel gym!). This will be the first vacation of my life where I return feeling rested and restored.
This time, Vacation Me will be different.
But, no. No, she won’t.
I will pack intentionally at first, with my little “capsule vacation wardrobe.” I will pat myself on the back, realizing there is still space in my bag. And then, in a flurried panic 20 minutes before I leave for the airport, I will shove three extra pairs of shoes, high-waisted jeans, four more pairs of undies, a gorilla costume (you never know!), and three going out tops into my bag, even though the only club I’ve visited in the last 15 years is Costco. I will check my suitcase because it’s now too bloated to fit in the overhead compartment.
My crusty old backpack weighs so much I cannot sling it over one shoulder or I will end up with a debilitating crick in my neck. Even though I’ve checked on the whereabouts of my passport thrice, by the time I’m five people away form the TSA agent, I’m frantically searching through my bag, sweating bullets. I finally find it in my back pocket, where I promised myself I would not place it.
I’m forced to chug the 14 ounces of water I forgot about in my reusable bottle. It makes me nauseated. I get scolded by TSA for taking my laptop out of my backpack. This is the last time I will touch my laptop until I return home. I hoof it to my gate in my athleisure pants that I just noticed are covered in dog hair. My flight isn’t even boarding yet, and I already have to pee. After I look at myself in the mirror— the straw hat I’m wearing makes me look like a child’s drawing of a scarecrow. The tag says “packable straw hat”, so I roll it up and place it in my backpack.
I really don’t need a coffee, but my flight doesn’t leave for 30 minutes, so I’m getting one anyway. I grab an Americano and a $22 bag of beef jerky. I immediately dribble coffee all over my light blue hoodie.
Eventually, I board the plane. I grab all my key items— kindle, phone, AirPods, book— and place them in the seat pocket that probably hasn’t been fully sanitized since 2021. I slide my backpack under the seat in front of me.
I plan on reading, but my Kindle is dead. Instead, I decide to watch a movie. But then the man in the middle seat next to me starts talking. He is fascinating. By the end of the flight, I know that in the 80s, he got shot by a rival gang and ended up moving to the Twin Cities to start a new life. He now owns an IT company in Brooklyn Park. He knows a lot about my life, too. I can’t decide if our hours of over-sharing was mutual? Or did I keep this conversation going? Did he? At any rate, we are now friends on Facebook.
After deplaning, customs, and retrieving my bloated bag, I find my hotel shuttle. I sort of try to cover my crotch as I walked toward the car as I spilled an entire ginger ale on my lap and it looks like I’ve wet myself. I buckle up and decide to listen to my audiobook on the long drive. I realize I’ve left my AirPods in the seat pocket.
I arrive at the hotel and unpack immediately. I hang everything up, or stow away the rest in the dresser, where 90 percent stay, untouched, until I pack back up. I will wear the same pair of shorts and tee shirt every single day of the trip. I try to wear my packable straw fedora to the pool, but it now looks like roadkill. I tie a scarf around my head, but it looks stupid. It’s okay; I’m more of a baseball hat kind of gal anyhow.
I never visit the hotel gym, not once. I take a daily walk on the beach, which is way more enjoyable. I never get around to learning about the yoga. I eat zero salads, instead dining on chips and guacamole poolside every single afternoon. I enjoy more margaritas than I’m willing to admit, and wake up with a mild dehydration headache every morning.
Before a nice dinner, I try on my fashion-forward Farm Rio dress, and immediately question if it was giving botanical circus tent when I tried it on at home. I opt for the trusty red cotton dress I wore all last summer, paired with metallic Birkenstocks. Metallic means fancy, right?
I read a few books. I get a little sunburned on the top of my shoulder, the same part I always seem to miss with sunscreen. I come home equal parts refreshed and exhausted, happy to see the family and responsibilities I craved a break from.
As always, I am just me when I am on vacation.
Who do you think you’re going to be on vacation? But… who are you really? Share with the rest of us!
This is a gem! I’m new to Substack, but it’s becoming my favorite.
So spot on it’s a little scary. Turns out no amount of Frank and Eileen matching sets will turn me into a person who doesn’t spill on herself at the gate. At least I’ve learned to buy navy and not white. Thanks for the morning laugh!