So You're Going on a Trip

Some people think preparing for a trip is incredibly stressful. To them I say, you’re doing it all wrong. Preparing for a trip is similar to foreplay: you need it to amp up the main event and make it even better. Unique analogy, but you get the point. Planning outfits, shopping for necessities, researching where you’re going to go - it rivals the main event itself. I want nothing more than for everyone to share in the love of this anticipation the way I do, and while I can’t change who you are as a person, I can walk you through ideas and lists that have proven tried and true to me and cross my fingers that they work for you. Now, lets start planning my fake trip together so this all makes a lot more sense!

The why, the where and the when

It all starts with why you’re going. Whats the purpose of your trip? Fun? Relaxation? Work? Funeral? Okay, the last one was dark, but its a possibility. Map out the why (could even be a few of those all mixed in) and the rest will align in terms of what to prioritize when it comes to your time and resources. Once you know the why, where are you going? Aside from being pivotal for practical things like where to buy a ticket to, it also controls the weather and what to look for regarding places to eat (a.k.a. priority number one) and things to do. Lastly, when are you going there? Can’t go skiing in the spring and no need to pack a parka in the summer. While these things can seem like an after thought, they can really shape your trip. These W’s are the core of your trip and everything revolves all around them.

For the sake of this guide, lets assume I’m flying back home to Miami for a week to visit family. The why is because I miss them and I want some quality time. The where - Miami, since thats my hometown and it houses the majority of my friends and family. The when being Thanksgiving week - that way I can optimize how many people I see in a short span of time since they’ll be together celebrating anyway and I can take less time off from work since Thanksgiving and Black Friday I have off by default.

Itineraries can be great to ensure you don’t miss out on anything, but they can also be a buzzkill. Commit to 3 things and/or 3 places you want to eat - let the rest be à la carte. If you put too many things on your ‘must’ list you are leaving out all of the spontaneous possibilities you won’t have room for. That being said, if you don’t cement those musts if they’re important to you, you may resent the trip (and its associated crowd) later. Make a top list and plan for those, the rest is we’re leaving up to fate. Also, whats a trip if you don’t nap? Gotta leave room for that.

For my Miami Trip, I want to make sure I do the following activies:

1) Shop on Black Friday (its a tradition, baby)

2) Go to the pool (I can’t do that in North Carolina in November)

3) Visit my favorite nail polish hole-in-the-wall gem (Lucky Nail Supply in Miami, the best)

Food wise, I want to make sure I hit up the following places:

1) Dos Croquetas (colada milkshake is to die for)

2) Graziano’s (iconic Argentinean place)

3) Marinos (real deal NY pizza)

I’ll plan for those via tentative calendar, but everything else is on the fly. Obvious but still good to point out: keep geography in mind. Since Lucky Nail Supply and Graziano’s are in the same area, I’ll do those back to back. Check the weather ahead of time too when you arrive if any of your activities are dependent on it (like my pool time). I may plan the pool for Wednesday, but if when I get there, rain is forecasted for Wednesday, we’ve gotta pivot. Also, share your musts with the people you’re either going to be traveling with or seeing, that’ll ensure they respect your wishes and help facilitate it. If going on a trip with multiple people, have everyone submit a must or two to ensure no one feels slighted and everyone gets to take something away from that time that matters to them.

The clothes

I am a carry on gal through and through! I used to not be though, but all it took was a taking a trip to Spain where I was the only non-carry on gal that I realized I was missing out. No waiting at baggage claim, no risk I’d lose it, and everyone still had everything they needed at their disposal. I decided that was going to be my last trip with a checked bag and I was going to figure out how everyone else did it. Now, there were some adjustments that had to be made, most notably, having to master the art of maximizing the minimum. Let me explain - do you need three pairs of jeans for a week? Absolutely not. What you may need instead is one pair of jeans and jewelry to distract and give the illusion you have more than one pair. Look, easier said than done, especially coming from me - I try to not repeat outfits and I love buying something I love in multiple colors, I am in no way a natural minimalist. It does force you to get creative and out of that headspace though, and you’ll be surprised at what good and unexpected combinations you can come up with when in a bind.

Most importantly - pack for where you’re going. Plan outfits around the weather and the type of things you’ll be doing. Are you going to need a bathing suit? Workout clothes? Formal? Lounge-y? Since I’m going for Thanksgiving, I know I need at least one dressy outfit. The rest can be pretty casual and I’ll make sure I toss in a few upgrade pieces (i.e. heels, clutch) in case thats where the adventure takes me. Also, do you have access to a washer/dryer? If so, you can seriously live in a bodysuit or two for a week (I’ve done it). These are all things you want to factor in prior so you can think through outfits accordingly and not need anything when you’re there.

The packing list

I like to make my packing list about a week prior to the trip itself, but the planning starts way before that. I start thinking if theres anything I need to buy prior (i.e. white sneakers) and use my list almost as a way to double check and review my own inventory. The best tip I can offer here is to follow your list - packing ‘just in case’ and ‘options’ is where you will fail. Write a list and stick to it, trust that you know what you’re doing!

I like to sort my list out by day, so lets assume I leave on Wednesday to Miami. The categories and examples of what would go in each would be as such:

Wednesday (Travel) - black joggers, grey sweatshirt, white sneakers, sports bra + socks (planes are freezing)

Thursday (AM) - jeans, black bodysuit, white sneakers, sandals

Thursday (PM) - black romper, black bra, heels

Friday (AM) - jeans, white button down, brown sandals, white bra

Friday (PM) - black floral skirt, black bodysuit, black bra, brown sandals

Saturday (AM) - bathing suit, cream palazzo pants, brown sandals (bonus points if you’re bathing suit and cover up look like an actual outfit, double win)

Saturday (PM) - maxi dress and brown sandals

Sunday (Travel) - black joggers, grey sweatshirt, white sneakers, sports bra + socks (yes, same for both travel days - no need to duplicate this one, especially if you have access to a washer/dryer)

Bathroom - shampoo, conditioner, body soap, facial cleanser, brush, comb, heat protector, blow dryer, makeup, makeup remover, contacts, deodorant, toothbrush, toothpaste, moisturizer, acne oil, ponytails, Turbie Twist, razor, towel dress and baby wipes (if you’re staying with someone who has these items up to your standards and are willing to share, ditch your own, its a no brainer, your suitcase is valuable real estate).

Miscellaneous - reusable cup, phone charger, laptop charger, miscellaneous bag, wallet, laptop, face mask, LMNT packets, sunglasses, black clutch and black sling bag (some of these things are personal preference, but good notes: an (empty) reusable cup is good to avoid plastic and spending obscene money on water bottles in the airport. Face masks are still required in certain places, bring it just in case. I bring LMNT packets anywhere I may drink a bit too much because they’re insanely hydrating and a great brand overall that my trainer actually approves of. I also like to be hands free bag-wise when traveling, my current favorite is the Billie Utility Crossbody from Bandolier)

Pajamas + undergarments - black joggers, oversized t-shirt and matching fuzzy set, slippers, underwear (1 per night + 2 extras just in case)

Jewelry - gold hoops, studs, ring stack, chain necklace (go super light on jewelry, super easy to lose and quite versatile if you pick the right pieces)

The away component

Just because you’re leaving for a bit doesn’t mean the world stops (sadly). A few tips on how to set yourself up for success before you take off -

• Block your work calendar as soon as you know your dates, just makes for less rescheduling later

• Block your first day back at work from calls/meetings, your email inbox will keep you busy enough, trust me

• Adjust your AC depending on the weather where you’re at, you can save a bit of money that way, no need to blast it if you’re not there

• Unplug any unnecessary electronics, even turned off they use power (crazy, right?)

• Don’t post that you’re prepping to go away or even that you’re away on social - wait to get back and THEN talk about your trip, the internet is crazy and you don’t want to make yourself or your home extra susceptible

• Make pet arrangements early! If your fur baby isn’t joining you, get them set up with a stay plan sooner rather than later since things fill up insanely quick (especially if your trip is during a holiday)

• Oldie but a goodie: leave a light on, preferably a lamp by a window to make it seem like you’re there

• Remember to set up your OOO email and slack message. Bonus points if its personal, this is my go-to:

  Hey there,

  Thanks for reaching out - I am currently out of office celebrating Thanksgiving with family and friends! Not to worry, I'll be back in action on Monday, November x.

  Our support team is still on standby, and they're great - reach out to them via email (xxx@xxx.com) for any technical or urgent questions and they'll get back to you ASAP.

  Appreciate your patience in the interim - have a fun holiday!

  Talk soon and take care.

The packing

Were you expecting me to tell you to roll all of your clothes? If so, you’re in for a surprise - I could do without. I personally like selective rolling, so only rolling the easily wrinkled pieces (it really does help with that) and putting them in between strategically laid flat folded ones. Rolled jeans to me are insane, way too bulky, those can lay flat as it would on a store tabletop and you’ll be just fine.

I do have a layout that I do think works best though for sectioning what goes where. My go-to that we’re working with is The Bigger Carry-On and The Everywhere Bag from Away (so worth the investment btw, had it since 2019). In the carry on, I put shoes, my hair dryer and bags in the zippered section, and on the other side, all the clothes. Then, in the bag, I use my handy Large Clear Cosmetic Case from Calpak for everything in the bathroom section of our list! On the sides of that bag, my laptop and purse essentials (i.e. wallet, chargers, etc) are easily accessible just in case I need them mid-flight.

The flying and/or the driving

Do’s and don’ts of actual travel time:

Do download all of your desired Spotify playlists and podcast episodes beforehand

Do charge your AirPods and their case prior

Do bring a photo of your Covid Vax Card (just in case you need it to do something or get in somewhere)

Do have exactly two mimosas pre-flight for the perfect relaxed but not too-relaxed flight experience

Do get to the airport 2 hours early for domestic and 3 hours early for international

Do a lil’ flight prayer if that’s your thing (my go-to: God, please bless this plane, everyone working on it, in it, on the ground and in the air. I pray that everyone gets where they’re going safely. Then I do an ‘Our Father’ and wrap it up with a ‘Hail Mary.’)

Don’t leave your battery in your carry on suitcase if you have one (put it in your bag that goes under your seat)

Don’t eat or drink anything prior to travel that your stomach doesn’t consistently get along with (i.e. Matcha)

Don’t get out of your seat immediately when deplaning, wait until everyone gets off (unless you have a connection, such a more relaxed experience)

Don’t get a window seat for a long flight, unless you love getting your sleep interrupted to get up

Don’t pass up a window seat for a short flight - easy access to snacks, the flight attendant and no blockers

Don’t forget to put your phone on low battery mode and if you close your eyes, lower the brightness even further to reduce battery burn out

The while you’re there

I don’t unpack everything, that’s a lot of unnecessary work if you ask me. Remember, you’re there to enjoy, not set up your new space for life. I only unpack my shower items, bring the cosmetic case to the bathroom and leave it on the counter and only hang up what is prone to getting wrinkled. The rest I just keep in my bag - the more you take out, the more you’re at risk of forgetting and losing when you’re packing to leave.

If you are tempted to buy something mid-trip, make sure you plan accordingly. Either that its small enough to fit in your bag or that you budgeted to mail it back to yourself. Thats why even if you have space to spare once you’re done backing, don’t be tempted to fill it and go off the list. That spare room will come in handy for the extras that will come along! See, that is why we stick to the list.

The checking out

Follow your list backwards! I repeat, follow your list backwards. Once you have packed everything back into the suitcase according to your list, do a review of the room as a whole - look under desks, check drawers, make sure you do a comprehensive review of the space before you go. Most places nowadays can and will offer to mail you forgotten items back, but they will charge you, and I rather spend my money on a real good Taco Bell spree.

The coming home

You are not going to want to do anything and that’s fine. For your future self though, you may want to push through that a teeny bit. I never understood why people didn’t like unpacking the same day they get home - all of it goes in the laundry anyway, so you’re just lifting a pile of clothes from one “bin” to another. Easy! It feels like you’ve done more than you really have and then when you go to shower and resume typical activities, everything will be ready for you. Unpack super quick and then go pass out on the couch with some pizza, you earned it.

Trips, even the sad funeral ones, are supposed to be enjoyable. The more you prep beforehand, the more you can actually focus on the trip at hand when you’re there. Happy travels!