The Keys to a Stress-Free Holiday Trip

Winter is often an unpredictable season that comes with crowds, inclement weather and other delays. Last year, overall holiday travel delays and cancellations were higher than in 2023, with approximately 96,300 flights canceled by U.S. carriers—a significant increase from the previous year. And this year could be worse, as 2025 has already seen its fair share of flight delays. Try to always book direct flights to lessen your chances of missing a connection along the way. Also, this is not the trip where you want your luggage to get lost as it gets transferred during a layover

The key is eliminating time at the X-ray machine. Before you get into line, stash your phone, keys, watch and belt in a plastic bag in your carry-on (or in an exterior pocket). After showing your ID, place it back in your wallet and put it in the bag as well. Then place your bag on the belt first, followed by your shoes, toiletries and computer. Your bag will come out first—making it easier to refill on the other side.

Your holiday travel schedule is often hectic and usually means you’re flying at the worst possible times, so treat yourself in order to make the process a little less hellish. Upgrade your ticket to “premium economy” or “comfort plus”, available on most major carriers. These are often the last tickets to go, so there’s likely seats still available. For a nominal fee, you get more legroom and perks like dedicated overhead bin space, early boarding and with some carriers, priority security access (no waiting in lines!) and free alcohol (two drinks and this just paid for itself). Trust us, you’ll arrive feeling so much better.

The best way to pack as much as possible while keeping your suitcase organized, these lightweight nylon cubes will help you compress bulkier items. Efficiently roll up puffy jackets, thick sweaters or pants and tuck them into a compact cube. Use each cube for a different clothing type (sweaters, underwear, pants) and peek through the mesh top to quickly identify what’s in each bag.

While the TSA doesn’t technically prohibit wrapped gifts, they do warn that “if your wrapped gift triggers an alarm, the gift might need to be unwrapped for TSA officers to resolve the alarm.” For this reason and to save you from having to lug a bunch of presents around for the better part of a day, we suggest shipping your gifts ahead of your arrival. This will allow you to wrap all your gifts at home and then simply unpack them at your final destination.

You know that traveling during the holidays requires planning. But that also applies to restaurants, movies, museums and even ice skating too. Have a spot you’re excited to try with friends and family? Make reservations earlier rather than later. Especially when you’ve got a larger group, calling ahead or securing tickets in advance ensures that you’re guaranteed entry and won’t have much of a wait.

Even for those lucky enough to get along swimmingly with family, a holiday visit can be exhausting and draining. Make sure you get a day to decompress. Before you head back to the office, schedule a day at home to stock up your fridge, catch up on laundry, hit the gym (or maybe more realistically, binge your favorite show) or do absolutely nothing at all. You’ll feel much more rested, recharged and ready for the New Year than if you jumped right back into work.

Add these to your standard grooming kit to look great the whole trip.