Let’s Get Away: A Winter Vacation Packing Guide

Unless you’re lucky enough to live in a tropical climate with year-round sunshine and mild temperatures, the winter months can often feel long and arduous. Once the holidays wind down, you’re faced with weeks of shoveling snow, defrosting the car, and bundling up in a parka for even the shortest trip to the grocery store. All that adds up to one universal truth about winter: it’s the perfect time for a vacation! Whether you’re planning a quick weekend visit to a nearby city or an all-out extravaganza on a faraway island, you’ll need a packing list before your winter break can begin. Here’s what we would bring along for five common winter vacations.

Ski Trip: Even though snow can be a struggle for day-to-day life, it does offer one major benefit: the opportunity to partake in winter sports! For the athletes among us, many cold-season vacations are filled with skiing, snowboarding, snowshoeing, and more. Even if you’re not so keen on snowy sports, you can still enjoy a wintertime break in a cozy mountainside cabin. If you’re headed out of town for a ski weekend, pack lots of comfy clothes that you can wear to relax beside the fire with a well-deserved cocktail once you’ve taken off your snowsuit and ski boots. We’d fill our bag with soft leggings and casual sweaters (the perfect combination for lounging if you have sore muscles after a day on the slopes), plus a stylish vest to top off your après ski look.

City Weekend: Because popular destinations are less crowded with tourists in the offseason, the winter months can be a great time for sightseeing in a new city—or visiting popular spots in your own hometown. However, you’ll need a wardrobe of warm and walking-friendly clothes to enjoy a weekend playing tourist when the weather is cold. When packing for a city break, keep layers in mind so you can easily control your temperature as you duck into shops, restaurants, and museums. Start with a lightweight top under a cardigan, and then layer on a warm coat and cozy accessories. And don’t forget the number one essential—flat, comfy shoes for all the steps you’ll get in!

Tropical Retreat: There comes a point in every winter when you’ve had your fill of snow and are in desperate need of sun, sand, and a poolside cocktail. A tropical island getaway or a Caribbean cruise can be the perfect remedy for the winter blues; it’s also a chance to break free from a wardrobe of tall boots and bulky sweaters. If you’re lucky enough to be taking a tropical trip this winter, make the most of the change in climate with a suitcase full of colorful mini skirts, breezy rompers, and sunglasses for long days on the beach. We promise you won’t miss your parka at all.

Valentine’s Day Getaway: When winter is at its gloomiest, Valentine’s Day provides the perfect excuse for a much-needed getaway with your significant other. If you’re planning a weekend trip that includes a romantic dinner or a night on the town, break free from the doldrums of your everyday winter wardrobe with a show-stopping new outfit. Keep things classic with a little black dress, or get into the spirit of the holiday with a colorful splash of red or burgundy. Whatever color you choose, don’t forget about your accessories—a pair of killer heels and a metallic clutch, perhaps, for a finishing touch of sparkle.

Winter Hiking: Much like popular tourist destinations in cities, national parks are a great place to visit during the winter months. The colder seasons offer a chance to see the sights without the crowds, and you’ll get to take in some dramatic vistas of snow-covered mountains and forests. If you’re planning a winter adventure in the great outdoors, it’s time to bundle up! Start by packing good foundations, like hiking boots, warm wool socks, and a few pairs of leggings that can multi-task as additional layers and post-hike loungewear. Top off your warmest down coat with a colorful scarf and beanie so you can take on the trail in style (and look great during any mid-hike photo-ops). Finally, don’t forget a pocket full of hand warmers to slip inside your gloves.

Where are you headed this winter? Leave us a comment and share your best packing tips for a cold-weather getaway!