What Do You Pack for a Cruise? Here's How Not to Sink the Ship

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If there's one thing I know a little something-something about, it's packing. I am, in fact, a champion packer. I could pack in the Packing Olympics, if such a thing existed, and I would bring home -- at the very worst -- a bronze medal. (Hey, it helps not to be too cocky about these things, you know? Truth be told, I'd probably get the gold, but I'm going to let you keep believing I'm modest.)

So when Kristen came to me with a packing challenge, I knew I had to step up to the plate.

The Packing Challenge: A festive two-week birthday cruise.

The Date and Place: February. Starting in San Juan, hitting seven other islands.

The Mission: "We'll be doing lots of active things," says Kristen, "so I don't know how many of those clothes I'll be able to wear again without washing. Also, I'm training for a race, so I'm going to actually work out and run while we're gone (wait, why are you laughing? No, really, I am. I am! But early, you know, before I start in on the boat drinks.) Any advice you have for packing without bringing 16 bags would be awesome."

So how do you pack for fourteen days on a cruise ship, doing active things, celebrating your birthday, looking spectacular while doing it, and not sinking the boat with your twelve tons of luggage? Well, my friends, I'd say we need to do a little multi-tasking. Here's how:

First of all, staterooms on cruise ships are notoriously small. Let's aim to get everything into one bag so Kristen isn't tripping over her luggage the whole time; if she's got a soft, fold-up-able one -- like a backpack or a big duffel -- that's even better. She can unpack and hang her clothes once she gets to the room and roll the bag up so it's not taking up valuable space in the stateroom.

I like to start packing by counting out the days I'll be gone and planning what I'll wear for each of them. Yeah, I know, it sounds a little neurotic, but it works---you'll find yourself crossing off pieces you thought you'd neeeeeeeeeed to bring in favor of those good old versatile black pants that go with everything.

Which brings me, fairly seamlessly, to Kristen's daytime staples; let's get those out of the way first. Since she'll be doing a lot of "active" stuff during her cruise -- which I assume means climbing and hiking and exploring, oh my -- I'd throw in four pairs of shorts (or capris, whichever she's more comfortable with. Personally, I always go with the latter, but she probably has better legs than I do.) If she can wear one of these pairs of shorts to work out in as well, so much the better, but let's add a pair or two of yoga/running pants too, so she can alternate between them.

When it comes to tops, I like to go with a half tank top/half t-shirt ratio; having the option to cover up your shoulders, either to protect them from the sun or because you're exploring a church or temple that might require a little more modesty, is huge. Since Kristen will be gone for 14 days and t-shirts and tops are fairly thin and lightweight, I might pack four of each, or possibly five of each, depending on space constraints. At least three each of these t-shirts and tank tops should go with at least two of the aforementioned shorts -- let's increase our potential to mix and match! -- and at least two each of them should go with ...

... a floaty skirt. Ah, the floaty skirt: Such a perfect vacation staple. Depending on the number of shore excursions that'll be less about climbing up volcanoes and more about shopping in exotic markets and sipping drinks in picturesque sidewalk cafes, I might bring two floaty skirts. They'll make a nice alternative to the shorts + t-shirt/tank top combo, and mixing them up with a variety of tops means Kristen can get at least three wears from one floaty skirt. If space permits, I'd bring one sundress along too.

Shoes-wise, I'd bring a pair of sneakers (make sure they can do double-duty on the outdoorsy stuff and the working-out-in-the-cruise-ship-gym stuff) and a pair of flip-flops to be worn with the floaty skirt, the sundress, and---on days she's not doing anything that requires a good grip---the shorts as well.

So that's the day stuff taken care of: Kristen will mix and match her t-shirts and tank tops with her shorts/capris and her floaty skirt. She'll throw the sundress on if she's feeling girly. But what about night?

First of all, I'd bring four nice dresses---you know, sort of cocktaily and fancy. If Kristen can squeeze in five, so much the better, but she could probably get away with wearing each twice and have nobody notice -- that's a nice benefit of cruise ships being big! Plus we'll talk more about how to get two wears out of each.

Does Kristen have a pair of nice tailored black pants? I'd bring those, for the nights in between the dresses. With three fancy "going out" tops, that's three more night-time outfits right there, which brings up to a total of eleven night-time outfits if each of the dresses above is worn twice.

Add in a nice cardigan or two -- bam, it can be added to one of the dresses, switching the look up a little. It can be added to one of the going-out tops, to get another wear from that outfit, or -- hold onto your hats! -- it can even be added to the aforementioned daytime sundress, to make it a little more evening-appropriate.

Shoes-wise, I'd bring one pair of pretty awesome heels that would go with all of the above; I find metallics -- gold especially -- often fit the bill. If Kristen has room, two pairs of awesome heels would be even better -- and bingo, another way to get double wearings out of those four evening dresses!

With the basics in clothing covered, I'd add three bathing suits, whatever underpinnings Kristen deems neccessary (with one spare thrown in for good measure), enough pairs of socks for working out, a sports bra or two and a couple of workout tops, a couple of chunky necklaces or dangly pairs of earrings---wacky acessories are my favorite way to change up repeat outfits when traveling---and a pair of sunglasses that she wouldn't cry over if they fell overboard. This is probably not the time to bring those Dior shades, is what I'm saying.

Last of all, my best piece of packing advice is to bring a pashmina: There is simply no end to the number of ways a pashmina is your best friend when traveling. Use it to cover your shoulders if you're visiting a religious site. Use it to drape around you at dinner if the restaurant you show up to turns out to be a little fancier than expected. Tie it around your throat as the world's most enormous statement necklace. Loop it, scarf-like, around your neck to keep you warm. Bundle it up and use it as a pillow if you need a nap in the tour bus on the way to the next shore excursion. I'm telling you, friends: Pack a pashmina.

So that's the bare minimum packed; I'd probably get this all in my suitcase, then add an extra t-shirt, dress, or pair of shorts if room permitted. I also always wear my bulkiest stuff the day I'm traveling -- the jeans, the boots, the hoodie; though I'm guessing Kristen won't really need any of that stuff on a Caribbean cruise, the lucky so-and-so -- bearing in mind that layers are easy to take on and off as appropriate.

Did this help, Kristen? I hope so! Best of luck on your cruise, and drink a rum punch for me if you remember. Bon voyage!

Want more packing tips? Mighty Girl's Maggie Mason shows you how to pack light for New York City. Rachel from The Window Seat shares her "less is more" philosophy. And Bella Online has some pretty comprehensive packing lists for any type of cruise.

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