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How to Pack for a Winter Vacation

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If you read travel publications and trawl the web for packing tips, you can find millions of words.

The most important, for winter sun holidays are “Don’t pack too much stuff, dress in layers, pack a hat and gloves!”.

To help convert general packing advice into a usable packing list, we have some tricks you can use to help figure out where to start. We’re not talking about packing for a ski trip—that is its own special challenge—but most travelers should find these winter travel packing tactics simple, straightforward, and useful for a more general vacation.

Hats—the Secret to Staying Warm

winter sun holidays

A light fleece and a warm hat are all you need to get from the car to a club, through the line, and back again without freezing — the same goes for sprints through airports, short walks for breakfast in the morning cold, and more. If you don’t want to freeze, wear a good hat.

Requirements for a good travel hat:

– Covers your ears.

– At least partly covers the back of your neck. 

– Has no flaps, fluff balls, or other wasted mass. 

– Is made of thin, modern materials for maximum warmth.

Shoes—Your One Heavy Item

winter sun holidays

Given that your feet are on the front line of most weather you will encounter, this is the one area that we recommend you be unafraid to go big. A solid, decent-looking pair of low-frills winter boots that you wear right onto the airplane will come through for you again and again during a winter trip.

Requirements for good winter travel shoes:

– Weatherproof.

– Light on lacing—you still need to get through security, so a pair of shoes or boots that can be worn loosely and don’t require a lot of tying and untying will help.

– Dark colored, so they won’t show stains from mud, slush, or getting thrown on security belts.

Gloves—Thin, Light, Breathable, and Waterproof

winter sun holidays

The days of massive mittens and wool gloves are gone, at least for smart travelers; you can get a great pair of warm, waterproof, yet very thin gloves that weigh only a few ounces and will take up only a few square inches of your luggage. The breathability makes them wearable across a wide temperature range, the waterproofing makes them useful in the worst weather, and the tight packaging makes them very low impact both when packing and when carrying them around.

Requirements for travel gloves:

– Weatherproof.

– Breathable.

– Extremely light and low bulk.

– Quick drying.

– Have some type of grip.

Clothing—Morning Paper Trick for Layering Up

winter sun holidays

Almost every collection of tips on how to dress/pack/stay warm/etc. in winter includes advice to dress in layers—which sounds great, but how do you go about it? Where do you start, and where do you stop? Without a plan, you could layer yourself up until you look like the Michelin man. To get a handle on how to pick and choose from the clothes you already own, try this trick.

When traveling during winter, use a “morning paper” approach to figure out what to pack:

– Light long- or short-sleeve shirt (or T-shirt) for reading the paper indoors.

– Long-sleeve top over that for grabbing the paper from the stoop.

– Fleece (or sweater, though wool tends to be bulky) over that for getting the paper from the curb. 

– Light wind- and waterproof outer shell over that for getting the paper from the curb in the rain.

If you pack such that you can get the paper in any weather, and then add and remove items as you go in and out of doors, you will have enough and the right clothes to layer up for pretty much any weather you will encounter, indoors or out.

Some Accessories to Consider


– Polarized sunglasses: Even weaker winter sunlight, when reflected off snow, can be rough on your eyes. In addition, the sun is lower in the sky, so is more likely to be in your line of sight or become a problem when driving during the short daylight hours. In those conditions, polarized glasses perform extremely well.

– Lower-body base layer: If you are going to be spending extended time outdoors, consider packing a base layer to keep your legs comfortable in the cold. They are harder to shed than a top layer, but don’t take up much packing space and are essential if you’ll be outside for hours at a time.

– In harsher weather, a scarf can be a small and light but very effective addition.

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