Winter travel can be magic: crisp air, glowing streets, slow mornings with strong coffee, and the rare, satisfying joy of watching snowfall from a train window or a mountaintop café. But it also comes with a unique set of challenges—and let’s be honest, not all of us navigate them like pros.
Whether you’re a seasoned traveler or planning your first cold-weather getaway, winter has a way of testing our planning skills, patience, and packing lists. And that’s where I come in—not to scold, but to gently guide you away from the missteps that can quietly sabotage a trip.
So let’s walk through 13 common winter travel mistakes that are more than worth avoiding this season. You’ll arrive smarter, warmer, and maybe even a little more relaxed.
1. Thinking “Layers” Means Just Throwing on More Clothes
Let’s start with the classic mistake: packing five sweaters and hoping for the best. Effective winter layering is about strategy, not bulk. The key is to build three functional layers—a moisture-wicking base layer, an insulating middle layer, and a weather-resistant outer shell.
Skip cotton (it traps moisture and chills you fast) and invest in merino wool or synthetics that regulate heat and wick sweat. A proper layering system can keep you warm and dry without looking like a snowman with a carry-on.
According to the CDC, hypothermia can occur even in temperatures as high as 50°F (10°C) if you're wet and not properly insulated. It’s not just about cold—it’s about staying dry and retaining body heat.
2. Booking Tight Layovers (Especially in Cold-Weather Airports)
A 45-minute layover might be doable in the summer, but in the winter? You’re just asking to spend the night on an airport bench. Delays, de-icing procedures, and unpredictable weather can quickly chew through your buffer time.
If you’re connecting through known winter hotspots like Chicago O’Hare or Toronto Pearson, aim for at least 90 minutes, if not more. A slightly longer wait beats a full rebooking scramble later.
3. Forgetting to Hydrate Because “It’s Cold”
Cold air might make you less thirsty, but it’s still drying you out—especially when you factor in altitude, heaters, and winter wind. Dehydration in winter is subtle but sneaky, and it can make you feel sluggish, headachy, and more prone to jet lag.
Carry a reusable water bottle, and sip throughout your travel day. Bonus points if you throw in some electrolytes during or after a flight.
4. Skipping Travel Insurance (Again)
If there’s one time of year to not gamble with trip protection, it’s winter. Flight cancellations, weather disruptions, even seasonal illness—they all spike during the colder months. Yet so many travelers still skip insurance, assuming it’s just an added cost.
Look for a policy that covers delays, cancellations, lost baggage, and medical emergencies. And if you’re heading somewhere remote or planning activities like skiing or hiking, double-check the fine print for coverage specifics.
According to the U.S. Department of Transportation, over 20% of U.S. flights experience delays or cancellations during the winter months—many due to weather alone.
5. Not Checking the Local Weather—Just the Temperature
It’s easy to check a destination’s daily high and call it a day. But in winter, you need a deeper read. What’s the wind chill? Will it be humid cold (which feels bone-deep) or dry? Are there icy sidewalks, limited daylight hours, or seasonal fog?
Understanding the feel of the weather helps you pack better and plan smarter. That sunny 5°C (41°F) in Madrid? It’s not the same as 5°C in Oslo at 3 p.m. with a wind tunnel downtown.
6. Wearing the Wrong Footwear (and Regretting It Every Step)
You can get away with impractical shoes in summer. In winter? Not so much. Slippery soles, wet socks, and aching feet are not the souvenirs you want to bring home.
Look for boots or shoes with insulation, waterproofing, and proper grip. And don’t forget warm, moisture-wicking socks—not just thick ones. If you’re planning city walking, comfort should still come first.
7. Assuming Public Transit Works the Same Year-Round
Some cities reduce bus and metro frequencies in the winter months, especially in smaller towns or off-peak areas. Others experience weather-related transit delays, or even close certain tourist routes during snowfall.
Before you rely on public transportation, double-check schedules and routes. And always have a backup—like a downloaded offline map, a taxi app, or the address of your hotel written down.
8. Underestimating How Quickly the Sun Sets
Winter days are short. In cities like Stockholm or Edinburgh, the sun can set before 3:30 p.m. in December. That means if you’re planning a packed sightseeing day, you’ll need to prioritize the outdoor spots early and leave museums or markets for later.
Build your days around the light, not the clock. It changes the whole feel of your trip—in a good way—if you flow with winter’s natural rhythm rather than fight it.
9. Packing for One Climate—Not the Transitions
A classic mistake: dressing for your destination but forgetting the journey. Airports, planes, train stations, and transfer cities can all vary wildly in temperature. You might be sweating in a down coat one moment and freezing in a thin hoodie the next.
Wear layers on travel days and pack a light change of clothes in your carry-on. If your checked bag gets delayed, at least you won’t be stuck wearing snow boots in a tropical airport or a T-shirt in a freezing train station.
10. Overbooking the Itinerary (Leave Room for Slowness)
There’s a particular kind of joy in slowing down during winter travel—lounging in cafés, browsing bookshops, or watching the snow fall from your window. But if your itinerary is packed from sunrise to bedtime, you’ll miss that rhythm entirely.
Leave room for slow mornings, spontaneous detours, or simply warming up over soup in a cozy restaurant. Winter isn’t meant to be rushed—and neither is meaningful travel.
11. Ignoring Cultural Holiday Schedules
Planning a trip over Christmas, Lunar New Year, or other local winter holidays? Great! But remember: many businesses, attractions, and even transportation networks change schedules or close entirely around these dates.
Research local holidays and customs ahead of time. Sometimes, being in a city during a festival is a dream. Other times, it means three days of closed museums and sold-out trains.
12. Treating Airports Like Afterthoughts
Winter is peak season for airport chaos—longer lines, more delays, and extra security slowdowns (especially if you're wearing multiple layers or boots). Add in holiday crowds, and you’ve got a potential recipe for stress.
Arrive early, check in online, and be strategic about your outfit. Wear slip-off shoes, avoid too many accessories, and keep your liquids and electronics accessible. Small tweaks go a long way when everyone else is fumbling through scarves and snow gear.
13. Not Packing for the Cozy Moments
This is one of those things most people don’t realize they’re missing—until they’re on a cold night train wishing for wool socks and a paperback. Winter travel invites a kind of introspection, rest, and comfort that’s different from summer energy.
So pack for that too. Bring something warm and soft to wear indoors. Load a playlist or audiobook for long, quiet evenings. Maybe even tuck in a journal or a small candle (yes, really). These touches don’t weigh much—but they anchor your experience.
How to Travel Like You Mean It
Winter doesn’t have to be the season of mishaps and missteps. In fact, it can be your most rewarding travel chapter—if you go in with eyes open and boots properly laced. The magic is real: crackling fires, empty museums, meaningful conversations over warm bowls of local stew. But so are the pitfalls.
Traveling like you’ve done it before doesn’t mean you know everything—it means you’ve learned to pay attention, adapt, and embrace the little things. It means knowing when to splurge on a better coat, when to slow down your plans, and when to say yes to an unexpected moment of stillness.
So go ahead: take the trip. Just do it with warmth, wisdom, and a little extra wool.
Travel Hacks Contributor
Cami is a former airline operations supervisor turned travel journalist. With a background in logistics and over 300 flights under her belt (yes, she counted), she’s the go-to expert for everything from navigating airports to scoring under-the-radar flight deals.
