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Overthinking It · Jul 24, 2026

How to Have a Perfectly Imperfect Vacation

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Sara Lieberman · Overthinking It

The first thing you must do to have a perfectly imperfect vacation is to pack several things you don’t need. For a vacation in Maine in mid-July, for example, that includes a denim jacket, a weather-proof jacket, and a hoodie. Plus, three “going out” (aka dinner) tops, mascara, bronzer, and some jewelry like bangles and dangly earrings. Thank goodness I knew enough to leave the curling iron at home.

The second thing you must do to have a perfectly imperfect vacation is to forget to pack several things you do need. Like, say, your favorite natural bug spray, a hat to shield you from the blinding sun while kayaking, hiking, and boating, and, most importantly, the credit card you used to book the rental car with points to save yourself $1,000.

But fear not! You do not let your preparedness and forgetfulness prevent you from having the Most Perfectly Imperfect Vacation ever!

In fact, the third thing you do is have oysters at a “Shuck Station” at the start of town, after which you realize most of the cute shops on Main Street closed while you were eating oysters and nearly choking on vinegar from an overly enthusiastic slurp. Of course, you still managed to buy some fishing rope coasters and a stained glass piece in the shape of buoys to hang in your apartment, so it all worked out in the end.

Next, you will show up at the waterfront spot with live music an hour before the band starts, and arrive at another after they sell out of chowder the night you were in the mood for it, but you will see an osprey in its nest at dusk and watch the sky turn from powder blue to rose to peach while sitting on giant granite rocks.

From there, you will do a U-turn to check out a darling boutique in a barn, only to realize it’s closed that day… But wait! There’s the owner, who pops out and offers you the keys to the barn! Quelle chance.

The following day is practically perfect from start to finish, from the beach to the candy shop to the farm hosting a one-night-only pizza party. You start to count your chickens…

…which is when they hatch as you have ice cream at an old-school spot along the route to your new Airbnb despite said new Airbnb being attached to an ice cream spot. (No regrets! Coconut Chip and Blackberry Chip FTW!)

I’ve lost count, but another thing you’ll do is embark on a hike alone where you’ll see a garden snake about 15 minutes up the mountain and nearly piss yourself. You will also dilly-dally post-hike by dipping your toes in a cool, clear lake, prompting you to show up at a café serving the blueberry pancakes you’ve been craving, only to be told they tossed the batter two minutes prior.

After spending stupid time Googling “best blueberry pancakes in Midcoast Maine,” you’ll say fuck it and settle for a smoothie.

From there, you’ll paint some “bleu, blanc, et rouge” on your face and choose the least vibey bar ever to watch the World Cup match between France and Spain, only to move to another bar at halftime, passing quite possibly the sweetest new lobster shack named after the owner’s dog, Rocky, which is where you’ll finally have your chowder.

Unfortunately, your quest to pick blueberries will be thwarted, but you will find a raspberry field and fill a pint for $6, followed by a walk through a sculpture preserve named for a famous Maine artist whose works you’ll then see at a museum and the airport in the following days!

You will have another ice cream (at the best lobster joint ever — zero notes; actually perfect), precluding you from once again having a scoop at your Airbnb, but at least the yoga mat you lugged across state lines went to use outside your cabin, overlooking the harbor as the sun rose.

You’ll feel a bit rushed through the museum you saved for your final day (because it was closed on the other two days you were in the area). Still, you’ll at least have plenty of time to drink the natural wine you bought from a producer down the road while playing Bananagrams with two dear friends and discussing past loves and the pros and cons of opening a second bottle. (FWIW: You opened it and didn’t finish it.)

The second-to-last thing you’ll do to have a perfectly imperfect vacation is drive past a blueberry seller on the way to the airport and snag a pint that you’ll lug through security so you can make Maine blueberry pancakes back in Brooklyn. (You’re going to want to bookmark this recipe.)

Then, finally, the last thing you’ll do to complete this joy-filled, imperfect trip of all trips is be so close to finishing the adorably cheesy TV series you started watching with your friend that you end up sharing headphones at the gate and then on the AirTrain, where you’ll catch the final sappy scene a minute before having to part ways.

In conclusion, and if it’s not already clear: I highly recommend the perfectly imperfect vacation. Forget your favorite bug spray. (You can buy some local stuff.) Miss the pancakes. (And make them at home.) Buy the unnecessary coasters. (Protect all the surfaces!) Nearly blackout from the sight of a garden snake. (Good story.) Eat ice cream whenever and wherever. (Always.)

Perfectly-perfect is overrated. Imperfectly-perfect is where the good stuff lies. A little bit of wrong, “oopses,” and zigs make the zags that much more memorable and gratifying.

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…whether to let the weather dictate my upstate plans or my attending an outdoor concert…

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