Nailed It! 5 Irreverent Tropical Vacation Packing Tips for Real People

Your hat is going to become a crushed, sweaty mess — and so are you. (Here's how to deal with it.)

The time is nigh. Your best plans have been laid. You laid them down so hard all over the place. You worked it out like you just started Cross Fit. Your PTO has been approved (and you're not one of those freaky people willing to lose a single vacation day).Your deposits have been applied. Your brother is feeding the cat. It is time to pack up and GTFO.

You are taking your Vacation-with-a-capital-V in a magical tropical location — a warm, sunny place where you will throw off your worries and exist, for however brief a period, as the carefree and beautiful living embodiment of the “rise” Instagram filter you have always known yourself to be. Your every thought and action shall be tinted with a dose of sunshine and the gentle glow of blissful nostalgia.

Now let's help you pack. Consider...

1.  Double the underwear.

If you are going for five days, bring 10 pairs of underwear. Make them cotton. If you need sexy underwear for your own personal sexy reasons, those are additional. You will put on one pair in the morning, then go out into the tropical heat for your days’ activities, such as running a marathon or walking gently through the shopping area in 99-percent humidity — either of which will feel like the same thing, dampness wise. Then you will return to your hotel and remove them to go for a swim of some kind. This will feel wonderful. After your swim it will be time for more activities, such as sitting and reading or going to dinner or hang gliding. Whatever you choose, you will not want to put your morning underwear back on. You need more underwear. On the flipside...

2.  Halve the shoes.

You do not need all of those shoes. They take up too much space in your luggage and you won’t wear them. No, you're wrong. This is right: You need two, max three, pairs of shoes.

You need a pair of flip-flops or your preferred beach or pool shoe. If these are Crocs, dispose of the Crocs and buy a pair of flip-flops. If these are Tevas, you're OK (though some will judge). Whatever you choose, these water-friendly shoes are the ones you will wear 99 percent. of the time.

If you are a sporty person with sporty plans, or a not-so-sporty, but still fairly adventurous, person with plans to be open to the idea of going zip lining or horseback riding or ATVing (or any excursion where closed-toe shoes are generally required), then also pack a pair of sneakers. These will be useful for the aforementioned activities and any possible sports, gym, or easy hiking you may do. (Of course, if you're planning to do intensive hiking, pack appropriate footwear for that.)

You will also want a somewhat fancier flat or sandal of some kind for going out to nice places for meals or dancing. Even the nicest place in a tropical location will find you to be appropriately dressy with your not-flip-flop (but also probably with your flip-flop) flats: You do not need heels. If you simply cannot believe this piece of advice, go ahead and pack a pair. They will take up way too much room in your suitcase, and you will only wear them because you want to prove they were worth wasting luggage space. And the night you do wear them, you will be like “Ugh, my feet hurt, why did I even wear these? I am on vacation. Why am I so mean to myself?” If you do bring heels, do not bring stilettos or any thin/pointy-heeled shoes, as they will sink into the sand, moist ground, or grass, spraining your tipsy ankles and ruining your pretty shoes you dragged halfway across the world for no reason. So go for a wedge or block heel. But also, hey, stop that — don’t bring heels.

3.  Triple the bags.

Only triple your bags if you usually have one bag, though. You need three bags to travel to a tropical location.

You need a cross-body mini purse. This bag can hold your passport, your wallet, a small sunscreen, your room key, your phone, and a few sundries like lipstick. I like to make this a fairly cute but not-flashy bag, meaning it’s simple and elegant enough it can be dressed up or down for use on nighttime outings and heading to lunch. Plus, it's hands free.

Pack a collapsible bag you can use for the beach or to carry the random stuff you buy on your walkabouts. This bag should scrunch or roll up small enough that you can pack it on your way to your destination, but unravel it and use it during your trip when you want to take everything that is in your small bag listed above, plus a book, a bottle of water, maybe your bathing suit or a change of clothes, a hat, maybe even a towel. You need this bag when you are going to be carrying a few extra things with you to the beach or a day's activity. This bag should be quick drying, or at least immune to water damage — like not leather.

And then you need your suitcase. Right, the one that does not contain any heels.

4.  Give your makeup a make-under.

You don’t need foundation. You need sunblock. Like so much of it. You will need foundation when you get home to hide the skin damage you will likely incur despite your best efforts, so leave it there. You are going to sweat it off, usually mere minutes after you put it on, before you even leave the confines of your air conditioned hotel room. I know you want it, I know it makes you feel like your skin is on, but you will not use it, and your skin will still be on and it needs you in a whole other way on this trip. Same goes for most other make up items like eyeliner and blush, but I get it if you want to bring that stuff for a night out, and it doesn't take up too much room. But definitely do not bring the highlighter. When you are flushed and sweaty in a humid climate this makes you look like you’ve taken magic mushroom; it’s a bad look. So you're done.

You need a hat. This hat will get destroyed. It will be a pain to travel withs. But still buy it before you go and carry it to your destination, as a hat will cost you three times as much wherever you land and be five times uglier, and also you will definitely get sunburned in the time between landing at your destination and finding a place to buy a hat. Get it at Target (or somewhere inexpensive that you feel good about shopping), because between the beach, the pool, the sweat from your sweaty face (see above), and being lugged between cars, boats, buses, or planes, this hat will be ruined. Make peace with that. You still need it.

5.  Bring a bottle opener.

Booze is spendy at hotels, and picnics are amazing — especially beach picnics with poke you bought at a fish market, or spicy fish sandwiches you scored at a street stall — and they all go better with beer you got for 15 percent of the hotel bar price. Also taking a bottle of wine down to the beach (or sometimes even just drinking it in your room) is nice. You would be surprised how many hotels do not have bottle openers in the rooms (to force you into a booze-lust-inspired room charge) but do not fret! These items need to be opened, and you can open them if you pack a simple (no multi-tool knives that will get snagged by TSA) bottle opener. This is the most important thing on here.

Now bon voyage. You got this.

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