Vacation Countdown Checklist: 2 Weeks Out to Boarding the Plane

Vacation Countdown Checklist: 2 Weeks Out to Boarding the Plane

Every trip has two versions of itself. There is the vacation you booked, and there is the frantic 48 hours before it where you are googling "does my passport expire" at midnight with a suitcase open on the floor. This vacation countdown checklist exists to kill the second version. Fourteen days, broken into chunks, so the only thing you are panicking about at the airport is whether there is time for a drink before boarding. (There is always time for a drink before boarding.)

Why a vacation countdown checklist starts two weeks out

Two weeks is the sweet spot. Any earlier and you will forget you did it. Any later and everything that needs to ship, get approved, or get refilled becomes a problem. The rule for the whole list is simple: anything that depends on someone else goes first. Your boss, the pharmacy, the pet sitter, the mail carrier. Anything that only depends on you can wait until the last weekend, because you were going to do it at the last minute anyway. We are not here to lie to each other.

14 days out: order anything that has to arrive

This is the day for the stuff with a shipping clock on it. Group costumes, the swimsuit you keep opening in a tab, refills on any prescription that will run out mid-trip, and the matching hats.

Put the hats first, genuinely. Not because we sell them (okay, partly because we sell them) but because a group order is the one item on this list that requires four other people to make a decision, and four people making a decision takes longer than shipping does. Start the group chat now, screenshot the options, let everyone fight about colors for a day, then place one order. Our hats are made and shipped in about two to four business days, so two weeks out gives you an enormous buffer plus room for one person to change their mind.

The hats to put in the cart

Out of Office Trucker Hat is the one that works from the airport to the pool to dinner. It is the closest thing we make to a neutral, which for us means it only has a cocktail on it. Good for the friend who wants to participate without committing to a bit.

Beach Please Trucker Hat is for the sand portion of the itinerary. Retro tropical design, mesh back, and it handles a full day of sun and salt without looking sad afterward.

Let's Get Shipfaced Hat is the cruise hat. If your countdown ends at a port instead of a gate, this is the one that gets photographed most, and the one strangers on the lido deck will compliment.

Mermaid Squad Trucker Hat is the actual matching-crew pick. Teal, loud in the best way, and it reads as a set the second more than two of you wear it.

10 days out: the trip planning checklist women actually keep

Boring but load bearing. Knock all of this out in one sitting with a glass of wine:

  • Check your passport expiration. Plenty of countries want six months of validity left.
  • Tell your bank and your card issuers you are traveling so nothing gets frozen on day one.
  • Confirm the pet sitter, the plant person, or the neighbor with your spare key.
  • Book the two reservations that actually matter. Not every meal. Two.
  • Screenshot your confirmations into one album so you are not searching your inbox on airport wifi.

That album trick is the single highest value thing on this entire pre-vacation to do list. Hotel, flight, rental car, any tickets. One album, offline, done.

7 days out: try it on, do not guess

One week out, do the full try-on. Pull every outfit you are imagining and put it on your body, with the shoes. This is where you discover the dress does not fit the way it did in March and that you have no bra for it. Seven days is enough time to fix that. Two days is not.

This is also when your hats should be arriving, which means you can slot them into the actual outfits instead of hoping. A trucker hat is the cheapest outfit repair in existence: it covers day-three hair, it survives being crammed in a tote, and it makes a mediocre airport outfit look intentional.

3 days out: the pre-vacation to do list nobody enjoys

Set the out of office reply. Do laundry now so you pack clean clothes instead of hopeful ones. Charge everything with a battery in it and buy the one charging cable you always forget. Pause any deliveries. Empty the fridge of anything that will become a science project. Do a currency and adapter check if you are leaving the country.

And decide your airport outfit now, so morning-of you has nothing to think about. Comfortable pants, layers, and the hat. Always the hat.

The night before: boarding pass energy

Pack the carry-on like the checked bag might vanish, because sometimes it does. One full change of clothes, swimsuit, medications, chargers, and your hat. Check in online, download your boarding pass, put your ID somewhere you will not have to excavate for it, and set two alarms. Then stop. The list is done. Anything you forgot at this point can be bought at a drugstore in a nicer climate.

Ordering for the whole crew

If your countdown involves more than one person, order together instead of separately. It is cheaper and it means everyone's hats arrive in the same box on the same day, which removes the "did yours come yet" thread from your group chat.

Here is how it stacks up on our site: 3 or more hats gets you 10 percent off, and 6 or more gets you 15 percent off. US orders of 2 or more hats also ship free. So the bachelorette party of eight is paying meaningfully less per hat than the person buying one for herself, which feels like the correct way for the world to work.

Assign one person to collect the color choices and place the order. Democracy is lovely, but not at checkout.

Keep reading

Start your countdown

The checklist only works if you start it, and the first item is the one with a shipping clock attached. Pick your hats, send the link to the group chat, and let future you handle the passport.

Browse the full Ship Show Co collection and get the crew sorted before the countdown gets loud.

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