Here's What To Pack For A Tropical Vacay In The Middle Of Winter To Look Cute & Be Prepared

by Kelsi Zimmerman

In my opinion, there is nothing better than taking a warm, tropical vacation smack-dab in the middle of a long, frigid winter. But if there is something that makes said vacation better, it's taking a tropical cruise in the middle of winter... one that doubles as a music festival. Lucky for me, I'm planning to board Holy Ship, an annual EDM music festival that takes place aboard a 4,000+ passenger cruise ship, early next year. But knowing what clothes to pack for a tropical vacation in the middle of winter, in addition to other accessories and essentials — especially on a cruise ship — can prove to be a challenge.

As if packing for this vacation during colder weather wasn't hard enough, Holy Ship's two sailings take place Jan. 5-9, 2019, and Jan. 9-12, 2019 — aka the coldest part of winter. With endless parties and performances on board, as well as a trip to a tropical destination, clothes, accessories, and beauty products that are weather appropriate, but also perfect for all of the festivities are a must. Obviously, though, when it's freezing outside my apartment, it's hard not to instinctively either throw my whole winter wardrobe into the mix or only pack bathing suits and forget that it still might not be that hot in the place I'm going. Plus, once you're in winter mode full-swing, you may forget to bring along some items you may subconsciously reach for in the middle of summer.

To help those lucky souls who might be taking a tropical vacation in the middle of winter (like to any of these destinations for NYE) like me, here's some intel on how to pack for your trip, as well as input from some experts... AKA some of the artists who will be cruisin' and performing during Holy Ship this year.


A Light Jacket

According to EDM artist and producer Manila Killa, making sure you have a light jacket handy is key when packing for any warm-weather destination in the middle of winter, as he advises not to let the warm temperatures of places like Florida and the Bahamas fool you. "Yes, [Holy Ship] departs from Florida and heads to the Bahamas, but the ocean gets cold, windy, and rainy at night," says the artist. "A jacket is essential. Last year I was sporting one I scored from the Urban Outfitters Women’s sale section. [It was] comfy, light, and functional."

Biker Shorts

Singer GG Magree also advises bringing along a jacket for a warm-weather trip, just in case, but shares that she also packs a T-shirt and biker shorts as her go-to vacation ~lewk~. According to the artist, her clothing essentials include a "Marilyn [Manson] T-shirt (because he is my A1), Nike biker shorts (to go under the Marilyn Manson T-shirt), dress-up clothes (be weird, embrace it), and a rain jacket (we dance rain, hail, or shine)."

Biker shorts, like these from Pretty Little Thing, are a great suggestion for a mid-winter tropical vacay. They're a super easy, comfortable, breathable clothing item you can pair with almost anything and wear to almost anything, whether that's exploring an attraction or heading to lunch, yet they'll still provide you with some warmth should a chilly breeze roll through.

Something Festive

When asked what they plan on packing for their tropical vacay, DJ duo Louis The Child add to Magree's point that it is important to pack "dress-up" clothes that are appropriate for the activities that you have planned. Do you have a formal dinner planned for one of the nights of your vacation? Be sure to pack a dress appropriate for a fancier affair. Or, if you know you're attending an event where there might be a themed occasion (something that def happens at an EDM festival), remembering to pack clothes that make sense for whatever those themed nights may be is key. "You don’t want to be the only person not dressed for the occasion," says the duo.

A Bathing Suit

As for me, I'm a sucker for catching rays (I'm going to this tropical destination in the winter for a reason, after all), so remembering to pack a bathing suit will be my number one priority to wear while lying out by the beach and pool, in addition to cut-off jean shorts that are easy to throw on over my bathing suit for casual day-wear or in case it gets a little chilly.

A Good In-Between Outfit

For the nights spent out and about that aren't too fancy, I plan to pack lightweight rompers and sundresses that are dressy enough for dinner and nightlife activities, but are still easy and breezy enough for the warm weather, and lightweight enough to pack in my suitcase.



What's equally as important as the clothes that you pack for a tropical vacation in the middle of winter are the accessories. After all, you may have to wear warm winter boots to the airport, but you'll definitely want to make sure you have sandals handy for the second you arrive to your (warmer) destination.

Manila Killa agrees, sharing that "a pair of comfortable sandals or slides [are] essential" to his packing list. And he's not wrong. Slides, in particular, are an easy, go-to option for shoes to wear on vacation, because they're guaranteed to be super comfortable, easy to slip on or off wherever you go, and, since they're not super luxurious, you won't risk messing them up when you're in the sand or on the pool deck.

A Simple Bag

Another important thing to remember to pack that you might not otherwise give a second thought? Something easy yet sensible to carry all of your stuff around in. A cruise deck or a beach aren't exactly the best places to break out that large, leather designer handbag. According to Manila Killa, he'll be bringing a fanny pack or shoulder bag to carry all of his essentials in. "You’ll want a place to keep your essentials and a fanny pack is a great, fashionable, convenient way to carry your stuff around. Last year I wore a black Fall/Winter 2016 Supreme Shoulder Bag," he says.

Sunnies To Protect Your Eyes

Yes, it may be winter, but odds are, if you're going somewhere tropical, the sun will probably still be shining. It's important to pack a cute pair of sunnies so that you protect your eyes from the harmful UV rays (while still looking cute), and GG Magree agrees that "fun sunglasses (I usually go to The Santee Alley in LA to grab way too many)" are among her top warm-weather priorities.

A Hat

You may also consider packing a hat with a wider brim to protect your face and hair from the sun's UV rays. Magree says "a Burberry Bucket Hat (for the mornings [she doesn't] want to be seen)" is her personal go-to. Believe it or not, bucket hats really are making a comeback, you know...


Hair Products That Beat The Heat

As a chronic over-packer and beauty lover, I usually tend to go way overboard (no pun intended) when it comes to packing beauty products for vacations. For a warm trip like Holy Ship, when it comes to my hair, I'll likely pack a dry shampoo like Tresemme's Fresh Start Volumizing Dry Shampoo, ($6, Ulta), since it'll get hot, and I don't need sweaty, greasy hair getting in the way (or in the photos).

Also, just because you're going to a tropical location, doesn't mean it won't be a little chilly or windy at times, especially at night or if you're by the water. You won't want to forget a frizz tamer or a hairspray, like Sexy Hair's Big Sexy Spray & Play Volumizing Hair Spray ($19, Ulta), to keep any flyaways and frizz at bay.

Lightweight, Waterproof Makeup

When you're out in the sun all day, it doesn't feel great wearing a full face of makeup and literally feeling it sweat off your face, now does it? Remember to opt for waterproof options, like L'Oreal Paris Lash Paradise Voluminous Waterproof Mascara ($7, Ulta), to ensure sweat and/or ocean water doesn't leave you with mascara tears.

If you still prefer a little bit of coverage on your complexion, pack an easy-to-use-and-apply, brush-on, powder sunscreen, like Colorescience's Sunforgettable Total Protection Shield SPF 50 ($65, Colorescience). The tinted powder formula will even out your complexion while soaking up any excess oil and sweat, while the SPF 50 will protect your face from sunburn.

Sunscreen, Sunscreen, And More Sunscreen

The guys from Louis The Child duo say that sunscreen should never be forgotten when packing for a warm vacation in the middle of winter. "The pool deck and islands get hot during the day! Make sure you’re lathered up in some of that sweet SPF 15 and get your tan on!" they say. "Some spray sunscreen is never bad, or get hands on with some lotion the old-fashioned way."

Other Necessities You Definitely Didn't Think Of

The combination of flying and having long days packed with a lot of activities in the extreme heat can definitely take a toll on your immune system and leave you dehydrated. But I, for one, want to make sure I am in tip-top shape throughout my mid-winter vacation. In addition to clothes, accessories, and your water-, sweat-, and heat-proof beauty products, GG Magree advises packing something like Berocca, a multi-vitamin used to prevent vitamin deficiency. You might also consider loading up your carry-on with immune system builders, like Emergen-C and Pedialyte Packets.

Something To Help You Relax During Downtime

Jimmy Vallance, from the EDM music duo Bob Moses, shares that an eye mask, ear plugs, and a good book are some essentials you'll find in his suitcase — all items needed for those rare, but valuable moments of downtime on a fun-filled vacation. Especially if you're going somewhere lively and warm, having something that helps you wind down at the end of the day is key. "Eye mask and earplugs [are] essential everywhere I go, but you do not want to forget them in this instance. When it’s time to escape and wind down ... there’s nothing like the cozy, quiet, and dark embrace of a good eye mask and earplugs," says the artist.

Motion Sickness Medicine (If You'll Be On A Boat)

For Manila Killa sea sickness medicine is a surprisingly useful essential to pack, especially if you're heading out all day on a boat. "Sea sickness is no joke. I never thought I had to deal with it until what happened at my last Holy Ship," says the artist. "I had just finished playing my set and ran straight to my cabin to... let the demons out of my system. Always remember the sea sickness medicine."

So whether you'll be attending Holy Ship this year (there's still time to book!), or you're planning to escape the cold weather by traveling to some other warm-weather destination, remember not to be fooled by the whole "tropical" thing, as it still may technically be winter, depending on where you're going. Pack what you need to stay calm, cool, and comfy in the sun, but don't forget to pack a jacket or two just in case. Bon voyage!