Travel Tips: Planning and Packing Process Hacking
I travel a bunch.
For instance, this year, I have been to London five times for business for at least a week if not two weeks, as well as trips to Paris, Dublin and New Orleans. Closer to home, we travel to Amherst, MA at least 4-6 times per year as well as a week each year with my in-laws in Martha’s Vineyard, MA, a week each year in San Juan, and a week each year with friends in Long Beach Island, NJ. Last year was about the same except that instead of Dublin and Paris, I traveled to Long Island’s North Fork, Mexico City and Amsterdam. You get the picture. Basically I am on a plane every other month, and on a multiple-day trip a couple of times per month via car or rail.
As you may imagine, this leads to a whole lot of packing and un-packing and of course means that for long stretches of time I must make do with whatever I’ve brought along or can find locally, from yoga mats to cocktail dresses to hair masks. I wanted to share the process I’ve developed to manage all this madness without turning up for two weeks of meetings in London looking - and feeling - like something the cat dragged in from under a hedge :)
Let’s dive in!
PROCESS PROCESS PROCESS:
I am a planner. In my personal life, as in business, my brain views the world as a miracle of rich overlapping systems and I long to understand, diagnose, anticipate and distill those systems into processes, which I can then replicate and refine over the years. A critical part of developing these processes is to capture requirements, which is why every trip, for me, triggers two workstreams. One, research, I will leave for a future post, except to highlight that research is critical to understanding what you’ll need to pack to be prepared for where you’re going, what you’re doing and how you’ll feel when you are there. Make sure you know the average temperature, humidity and rainfall, identify the key itinerary items and activities you plan to participate in at your destination, and look up any relevant dress codes.
Data is your friend!
The second workstream is documentation.
DOCUMENTS DOCUMENTS DOCUMENTS:
My go-to documents duo is a Google doc and a to do list. I like to keep my to do on my iPhone reminders app. My Google doc format is usually either a text doc or a spreadsheet, depending upon the type of trip. For work trips, I do a word doc because my work schedule (i.e. the bulk of my daily activities) is already captured in my work calendar, whereas for personal trips I create a spreadsheet with 2 columns for each day: one for activities and one for outfits, plus a row for each time slot from breakfast to after dinner. Yes, I plan my day around my meals. Don’t you? :) Either way, you are making a list of every item you need for each day you won’t sleep at home, so make sure to include travel days, as you need plane clothes, too.
This is my spreadsheet from our recent Spring Break trip to New Orleans with our daughter.
The to do list is critical because you will remember things you need to do at times when you cannot do anything about them. Needing to take a bridesmaid gown to the tailor or pause a Sun Basket delivery, to clean out the fridge or confirm dates with the kitty sitter, etc. will all occur to me in the middle of a video-conference call, or while I’m tucking and bend-extending my way through an hour-long Barre Method workout. Actually in the latter case even my iPhone can’t save me and I switch my wedding ring to my right hand, to trigger me to make a note back in the locker room. You can steal this trick, if you’re a creature of habit.
Once you’ve established the docs themselves, it’s time to get documenting.
To start, I begin to list the individual pieces I need for each activity in my Google doc. If on, a given day, for instance, I am planning on hiking in El Yunque National Forest, eating lunch at the Kiosks in Luquillo, and then hitting the stunning beach there for a couple of hours in the late afternoon before going home to shower and change for dinner at neighborhood gem Santaella, in San Juan, that list would look like this:
Jungle/Mountain Hiking:
Black Outdoor Voices sport dress, white ankle socks, gray crushable sneakers, white baseball cap, plus wedding ring, Mejuri star stud earrings, small canvas tote bag
Lunch:
Above, with sneaks and socks swapped for gold Havaiianas, so I can dig my toes in the sand while I eat, and swap the baseball cap for a straw Panama hat, and then I tuck the canvas tote in the straw beach bag to protect my phone and wallet from sand.
Beach:
Large straw beach bag prepacked with black bikini, black and white swimsuit cover up, straw Panama hat, gold Havaiianas, two towels, sunscreen SPF 30 and 50, Sun-In Spray (to make the fine hairs on the body turn gold), Kindle, Herban Essential face wipes, hair mask, wide-tooth comb, and a black bandanna to hold hair and mask back from my face and protect my Panama.
It’s me!
Dinner and Drinks:
Maison Tallulah red ruffle floral midi dress, red lace bralette, shapewear shorties, cognac suede sandals, my beloved tan Gucci Soho Disco crossbody, Mejuri gold threader earrings, gold lavaliere necklace, vintage Piaget rose ring, Mejuri stackers, wedding ring and engagement ring.
After I complete this exercise for every day of the trip, I then take all the items from each day and begin to compile a master list of everything I will need to pack for the trip.
For instance, the example day above yields:
Black Outdoor Voices sport dress
Black and white swimsuit cover up
Red ruffle floral midi dress
Bathing suits: Black bikini
Undies: Ankle socks, red bralette, shapewear shorties
Shoes: Crushable sneakers, gold Havaiianas, cognac suede sandals
Headgear: Baseball cap, straw Panama hat
Jewelry: Wedding ring, star stud earrings, gold lavaliere necklace, Piaget rose ring, Mejuri stackers and threaders, engagement ring
Bags: Small canvas tote bag, tan crossbody
Products: Sunscreen SPF 30 and 50, Sun-In Spray, face wipes, hair mask
Personal items: Kindle and charger, wide-tooth comb, black bandanna
Here I am in New Orleans in my Outdoor Voices sports dress, which I adore. True fact: I am wearing free aviator glasses because I left mine at the Air BnB. They are free because they are bifocals. This made city biking way more exciting than I ever thought possible. :D
As I continue to build out this list, adding the items for each day’s activities, I add to the categories (e.g. bathing suits, undies, products, headgear, personal items. That prevents duplication. Don’t forget undies such as strapless bra, shapewear, etc.)
Three key tips come into play at this point:
Rely on a color scheme. The day above is leaning into clean black and white for daytime, with neutral and gold accessories. As I continue to build outfits, I can leverage this color scheme to ensure that the majority of my pieces go with each other, and so I can improvise if desired. This will also ensure that I always look pulled-together and intentional. Black and white is easy. I personally also love navy and white, all-neutrals, and of course, all-black. Other easy options: black and gray, gray and denim, etc. Once you get used to thinking this way, it becomes second nature. and even helps you build and maintain your regular wardrobe by buying quality pieces that go together.
Accent color (or neutral) accessories such as shoes, bags, jewelry and scarves will then serve to liven things up. For instance, red and hot pink work well for black and white and for navy and white, though you could also do cobalt or cognac with either. For all-black or gray-and-denim, work in some caramel or beige or splash out with midnight blue, bordeaux or amethyst. Try to pick your evening wear clothing in accent colors, so you don’t feel like you’re in color-scheme prison, and so your whole look is extra-polished in the evening with a coordinating handbag, shoes, and accessories. Keyword here is coordinating as you don’t want to veer into matchy-matchy.
Make a point to develop outfits which re-use key pieces, particularly those which take up the most space in your luggage, such as denim, sweaters, coats/jackets, bags, sneakers (pick a pair that will work for both casual and workout scenarios, if possible, and try to wear them on the plane) and hats. Stick to your color scheme especially when considering these key pieces.
Use the three-pair shoe rule. Figure out the key footwear items you need for the trip and limit to 3 pairs, apart from your sneakers (plane) and beach shoes (flop flops squeeze in anywhere and don’t count.) That might mean a pair of good sandals, a pair of high heels, and a pair of flats in the summer, and a pair of low-heeled ankle boots, a pair of high-heeled knee-high leather boots and a pair of low-heel suede knee-high boots in winter. This will also vary depending on whether you’re headed to a warm or cool climate. Again, consider and stick to your color scheme so you can improvise as needed.
Now that you have a list of what you will need for each day, don’t forget to consider and count your basics. You’ll need sleepwear, workout gear, toiletries, chargers, medicine and vitamins, work gear and even special stuff like a full bridesmaid outfit or sporting equipment. List away.
Time for more TIPS!
TIPS TIPS TIPS:
Organization is your ally, so I rely on three levels of containment, namely packing cubes, pouches and purpose-built cases.
Packing cubes: These come in a variety of shapes and sizes. The best ones allow you to pack like items together and see what’s inside each cube, so you can put all your undergarments in one, PJs and workout gear in another, shorts and tees in a third, etc. When you get to the accommodations, you take them out of the suitcase, pop them into your drawers and you’re done! As items get dirty, wash them in the sink with shampoo and hang them to dry on a hanger in the bath, or pop them in one of the hotel’s own disposable laundry bags, or your own, folded conveniently flat in the bottom of your lingerie packing cube with dryer sheets inside. Packing cubes are also great for small fragile things like travel candles.
Pouches: I corral all the electronics chargers and gizmos in one, my ‘bedtime gear’ of dental guard, sleep mask, ear plugs, vitamins, mini hand cream, lip mask in another one, another one holds basic makeup items and is sized to go in the cross-body bag for touching up on evenings out. Generally I get these from Premium Economy on business trips, and am not above picking them up as I deplane, especially if someone’s left an unopened one behind in Business Class :) Waste not, want not, right?
Purpose-built cases: laundry bags, toiletry bags and garment bags, jewelry case: I always pack a laundry bag to keep the clean and not-clean separate. If you, like my husband, have a ‘middle’ category in between, well, you’re an adult and you decide! For instance, I don’t wash my denim after every wash but I do rub with a dryer sheet and hang up… Toiletry bags are serious business. I have one prepacked with travel size jars from the drugstore and samples, plus five days worth of contact lenses, and some treats like a bath bomb and perfume samples. Live a little. I have a second toiletry bag for inevitable longer and/or more complicated trips where Advanced Beauty Protocols are invoked, and I need hairspray and self tanner. Finally, your garment bag exists to hold long items like dresses, wrinkle prone items such as shirts and silk blouses, and crushable things like suiting. Keep the dry cleaner plastic as those layers between each garment will further safeguard against wrinkles and allow you to sneak more items inside the garment bag.
STAGING STAGING STAGED!
When the trip gets close, I start staging. depending on the trip I can start this up to two weeks in advance. I use the padded bench/trunk/ottoman in our bedroom, inside which is where most of my folded clothes live anyway.
Set aside an area for the items on your packing list. Bust out your packing cubes. Pull up that packing list. Are you ready? Ok. Time to stage has come around! This is really soothing for me. I am a savourer of anticipation, so staging allows me to really marinate in the delight of an upcoming adventure. Additionally, I experience anxiety in my life, so I appreciate being able to take modest and measurable actions that add up to progress against large tasks over time. If I have a huge trip coming up, looking at my staging area is like taking a cool shower on a hot day. You should see my Christmas gifts corner. (It’s behind the laundry.)
Scented dryer sheets keep your belongings smelling fresh throughout your trip. I make sure to keep a box of the most yummy-scented dryer sheets I can find inside my nested packing cubes when I put them away for storage between trips. As I start staging, I tuck two sheets into the bottom of each packing cube I am using.
Okay, the next time you’re in a bit of a tizzy, look at your packing list and figure out which items you will and will not be using between now and your trip. Are they clean, shoes polished and protected? Do clothes need a button or a hem? Pull the items you will not be using and roll them up, if they’re not already rolled, then begin arranging them into the relevant cubes. When you’ve exhausted the list, put each cube back on the staging area. Do the same with your garment bag and your toiletry bag and your pouches.
You can do this either a teensy bit at a time, in batches, or all at once. Know that you won’t be done-done until right before the trip, but that you are making visible progress. There are a lot of opinions on rolling vs not. When I Kon-Mari a drawer (I’m doing it in batches!) I now put everything back rolled, because it allows you to see everything much more readily than when you fold and stack items in drawers. For travel, with packing cubes, visibility can only help, and since the packing cubes have convenient mesh tops, make the most of it by rolling folded items into cylinders, and pop them into the cubes like Mari Kondo do.
As you pack items, mark them emphatically complete on the packing list. I like “DONE” but “EXECUTED” is also zippy, especially in boldface font. Listen to a podcast, deep-condition your hair, and drink a vodka soda from a sippy cup, too, while you’re at it. Take deep breaths. Make a pile for the tailor, laundry and dry cleaner. Rinse and repeat as needed. If you have more space, you can even do this INSIDE YOUR SUITCASE! This leads us to…
PACKING PACKING LEAVING
Take a look at the suitcase, amigo. Peel off old travel stickers and tags. Make sure the inside is clean. Note which side is up and layer the heaviest items and the most sturdy in the area which will be the bottom when the suitcase is standing up. That means your winter boots, beach towels, rolled up totes and umbrellas, jeans, tees and sweaters will be all on on the “South Pole” and your lingerie, swimwear, delicate footwear and handbags, toiletries and styling tools will be all on the “North Pole.” If your suitcase has a half with a fabric covered zip section and a half with straps that click together, separate the delicate footwear and bags, and anything that can be stained from the heavy items, tools and toiletries. I like to double-bag the toiletries bag(s) in plastic bags, since I once had had a bottle of DayQuil spill inside my luggage on the way to Puerto Rico. I am surprised that I didn’t actually cry when I discovered that the contents of my suitcase were dyed electric orange, and that I had to hand wash and hang dry them in the bathroom, while sick with a raging head cold, sans the comfort of the Quil. Live and learn, or double bag.
Next, you can tackle the items you will be using between now and departure day. Inspect these and make sure they are all clean and in good repair. If not, add them to the tailor/dry cleaner/laundry stacks and address as needed. As you launder them, decide whether you’re ready to pack them or not and “EXECUTE.”
Set your airplane outfit aside. In addition to your sneakers, this will include the bulkiest coat you plan to wear on the trip. You can use it as a sleeping bag on the plane! For other coats/jackets, I like to flip the garment inside-out (sleeves too) and roll them lining-side out for packing. This prevents staining, pulls and scratching of your leather jacket or blazer, especially if you’re not doing a garment bag.
Pack your jewelry away in its case, and stash it in your carry on along with the relevant pouches. Double check the electronics gizmos and make sure you’ve got at least one adapter (2 is better, you want to be able to style your hair while you charge your phone.) Identify anything you will need at the airport when you land (change of shirt and shoes to snazz up for sightseeing? small tote or crossbody instead of carry on?) and make sure its visible and easy to grab without unpacking your whole bag.
Finally I like to pack pouches with things I will need on the airplane and stash them in my carry on. This might mean my ‘bedtime gear’ and glasses + contacts pouch, if it’s a long flight. Even for short flights I like to have a couple of herbal wipes to disinfect my plane seat, lip balm, Caudalie face mist, my travel toothbrush/paste/floss kit, Kindle, iPhone and charger. Stash liquids in a see through plastic pouch for easy TSA scanning.
At the end of this cycle, you will have crossed everything off your list. Double-check the list!
Are you ready for your adventure? If you have amazing travel packing or planning tips to share, please leave a comment!
Bon voyage!
