10 Vacation Packing Tips for Success

Dress for the vacation you want, pack for the trip you have.

I am currently out of office, or as they say in the biz (corporate America), OOO. I am taking a vacation from regular scheduled programming. This means no Zoom meetings or essay editing. It also means putting off my contractual obligation to eat at a certain buffet chain twice weekly (sadly, this is true).

As we speak, I am overlooking orange and olive trees. Beyond them are curvaceous rows of Portuguese grape varietals that I can’t pronounce. This fertile land, with an offensive amount of nature’s bounty, rolls up and down before falling into the Douro river. It is a living postcard. Or simply, an earthly paradise for anything with a heartbeat. 

Here, even the birds are cocky.  

Sitting on the vineyard’s edge, I am slathered in sunscreen and chewing a preventative Pepto Bismol™. As I stretch out in curated clothing and well-grooved Birkenstocks, I can’t help but marvel at the things my past self did to bring me to this very moment. Specifically, how my pale, depleted body managed to anticipate my vacation-selfs needs so well.

And this starts and stops with a perfectly packed suitcase.

To shop your home and cobble together a flawless vacation bag is as much an art as it is a science. It takes years of experience and experimentation.

So, gather round as I share my tried and true vacation packing tips for anyone over 30.

1. Take your age and divide it by two—this is how many pairs of underwear you will need for a 10 day trip. E.g. if you’re 30, you will need 15 pairs. If you’re 63, round it up to 32 bloomers (to be safe).

2. Bring enough Gravol™ to euthanize a small horse. You never know when a fateful bout of insomnia or travel-related illness will take hold of your fragile, vitamin-D deficient body. 

* Do not underestimate your dimenhydrinate tolerance after consecutive use. 

3. Stuff in your orthotic inserts. Never discount the power of hip realignment to give your little black dress that “je ne sais quois”. The same goes for compression stockings. 

4. Load up on Ombrelle’s 70+ SPF sunscreen. Counterbalancing prescription retinol with anything less than concrete plaster is a gross injustice.

5. You’re gonna need the fanny pack. While fanny packs have mysteriously made a comeback, the sleek, fashionable options are not for you. You want the oversized, Grinch-that-stole-Christmas sled of a fanny, expandable with droopy pouches for loose Gravol™ pills, ketchup packets, and nerdy carabiner clip-ons.

6. Bring a bottle opener. While we’ve grown accustomed to the ease of twist-offs, Europeans are romantics that enjoy procedure and cork. You never know when you’re going to need to crack a Vinho Verde on-the-go, on a train, or at the Airbnb you cheaped out on. Plus, airport customs consider the mini-knife of a wine opener a weapon, so utility and security?

7. Toss in a purse pen. While you may have organically entered the “purse pen” phase of life, rest assured, there was a time when carrying a pen would have been ludicrous. Too organized. Too mom-like. Post-30, you are now the pen that the disheveled 20-somethings rely on for custom forms. Pay it forward. Be the pen you wish to see in the world. 

8. Don’t forget the neck pillow. Whilst there is no greater visual tragedy than a travel pillow clipped onto a roller suitcase, if you’re flying economy, it’s your reality. The limp pillow avec Gravol™ is your only hope for a stiff-necked nap. So, bust out your Las Vegas skyline donut with matching eye shades and dream of free upgrades.

9. Get noise canceling headphones. Sure, you’ll get a pair of freebies from the airline to watch Magic Mike’s Last Dance. But can they block out the coughs, cries, throat clearings, annoying questions, and couple’s quarrels from your tin can comrades? No, they can’t. If you’ve got em’, pack em’, and slip into sensory-deprivation, self-preservation.

10. Cram in an easy-breezy book. A real, paperback book—while hefty—is a luxury well-afforded on vacation. Reading a book permits hours of nothingness, and unlike TV binging or phone crunching, it’s respectable. At your destination, a book is a gateway to honourable laziness. People will love you for reading a book. Strangers will celebrate your old-timey sophistication. Partners will not judge. And most importantly, impromptu siestas will happen. 

See you next week for Back to Shameless, back in North America. Subscribe below?