Commuting from Maryland to New York during the holidays doesn’t sound like a rip-roaring good time, but you don’t understand—I take the train. For yours truly, that three-and-a-half hour Amtrak train hustle is an absolutely thrilling whirlwind from the mid-Atlantic to Penn Station. After that, sprinting around Manhattan for eight hours before the three-and-a-half hour return trip requires a special set of skills. It requires an intensive amount of prep (at least if you're a kook like me) to keep a tight grip on your fate and the will to do it all over again next time duty calls.

Failing to prepare is preparing to fail! It’s taken me years of obsessive Googling, list-making, and the occasional trial and error (getting stuck underground in a non-AC face-melting subway for 45 minutes drenched in sweat from armpit to waistband) to come up with a fail-safe safety net of goods that I can carry—literally—close to my heart. If the content on this page are my last will and testament, I will be happy with that. This is the best of my best for you guys.

First things first

Start with a strong base: the perfect travel bag into which you can put your undying love and utmost trust. Caraa Sport makes this futuristic, insanely luxe ($$$, sorry) carry-all that feels like something I dreamt up during my wildest nightsweats. It features the most efficient qualities of your duffle bag and backpack gogo-gadget-ed into one jacked up, Italian leather, super bag. Bottom half is for a proper pair of shoes (with fresh socks tucked inside) plus your laptop. The top half keeps your other doodads pristine, perfectly pocketed and safe. My alter ego bag that I use for smaller travels is a diaper bag. I don’t have a baby (lol) but I am a always-prepared Capricorn dog mom who values a thoughtfully placed pocket (or six).

In terms of storage within my bag, I took a note from my mom who invests in matching zippy cube sets that somehow make meticulous planning a soothing activity. My current favorites are from Leatherology and come in a set of three different nesting sizes...AKA packing p0rn.

Doodads

There are two categories here: necessary-to-survival hygiene products and added bonus feel good supplies. Under hygiene, I am one of those neurotic people that brushes their teeth after lunch and swipes on a little (a lot) of deodorant mid-day. You’ll never catch me without my Quip toothbrush ready to rumble. Deodorant-wise I have a special one I reserve for travel from Chanel that smells like my man because I’m corny and it gives me a lil boost, emotionally and physically. To quickly freshen a not fresh neck/hand/tray table (and honestly sometimes my pitters) I’m obsessed with these individually wrapped essential oil towelettes from Goop.

In terms of feel good supplies, having five to eight assorted lip balms on hand at all times is crucial. Fave for the basic quenching lip thirst is a bebe Vaseline pot with a rose tint to it. Buy this even if you don’t want too, seriously. Fave for a lewk is the YSL Liquid Balm that gives you the oomph and sheen of lip gloss with the hours of moisture factor a heavy lip balm gives.

To grab my youth by the balls and encapsulate it for a lifetime, I love to keep eye cream on hand 24/7. My favorite is from Eyeko that has a vibrating tip BUILT in (depuffing machine) and packs in cooling and brightening powers beyond belief. Regardless of where I am and what I’m doing, there’s a mini-sized jade roller in my bag. I have four (Mount Lai is the best) that have their respective place in a bag, bathroom, coat pocket, etc. that I like to roll over stress areas like between my brows to keep me zen at any time and bring me back into my own headspace.

After all that noise, I keep the clicky click pen YSL concealer with me as well. It immediately makes me feel 10% more luxurious and gently tucks in blemishes and any signs of sleepless chaos away for safekeeping.

I used to try and find “smaller” things to take on the go but it feels more on brand for me to carry a glass jar of hand cream that smells like banana pudding instead. Last but absolutely never least, a rollerball oil fragrance that smells like a fresh shower can make a momentous difference. Child perfume makes me smell like I sleep in a meadow of fresh flowers and rise with dew drops on my eyelashes! Plus, I read somewhere that John Mayer loves and easily recognizes this scent when in his presence, just saying.

Fuel

If you’re not proactively thinking about potential hunger meltdowns arising, we need to talk. Never trust a person who isn’t thinking about their next meal. I wouldn’t even joke about skipping my overnight homemade cold brew. I make it in this and then pour it into my leak-proof double-wall vacuum insulated travel mug in the morning. I’m really here for this new crystal energy glass water bottle because we’re all just looking to experience more presence and emotional protection in this adventure called life.

Miscellaneous life saving items

Rohto eye drops, a pack of matches (thank me later), multiple pairs of large sunglasses (for hangovers, hiding from enemies, confidence boosts, and more), a gold metal hair claw, Tide pen, external battery pack (mine is bedazzled, obviously), a switchblade (my Grandma taught me to use nunchucks as a kid but those don’t fit in my bag) and canned wine...depending on the day.

—Samantha Wilson

Photographed by the author.