Tips from a travel pro to survive the chaos of holiday season with ease
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- Book direct, early or holiday-morning flights; monitor weather and rebook early.
- Pack carry-on with essentials, protect fragile gifts, wear coat to save space.
- Prepare backup flights, call airline or app on cancellations, and buy medical insurance.
I’m just going to say it: Travel these days is rarely glamorous or easy. And during the holiday chaos, we’ve all seen the images on TV or social media of weary crowds sleeping in airports or losing their cool, thanks to weather delays or mishaps that lead to missing cherished holiday celebrations.
As a professional travel journalist who travels weekly, here are my tips for making holiday travel as smooth as possible.
Think outside the booking box
By now, you know the general travel advice: Book airfare well in advance to get the best holiday fares, and choose early-morning flights since they’re less likely to be delayed. But I’m also strategic about when I travel, avoiding notoriously chaotic travel days like the Sunday after Thanksgiving or Christmas. I always book direct flights — even if it means a bit of extra driving.
I also love flying out on the day of a holiday, like Christmas or Thanksgiving morning, as most people are already at their destinations. And I closely monitor the weather forecast; if it looks like a big storm is coming on the days I’m traveling, I’ll try to rebook my flight for a day or two earlier to beat the weather. I realize not everyone can do this, but if you have the flexibility, it can help you skip major travel headaches.
Travel smart and light
While this is my general rule any time of year, during the busy holiday season it’s essential to pack as lightly as possible. I usually throw on a crossbody bag with my essentials — such as my ID or passport, phone and charger — and then bring a carry-on suitcase to be stowed above my seat. With unexpected delays and fears of lost luggage, I always like having everything with me. Plus, breezily rolling on and off the plane is a travel flex.
If I’m headed to a cold-weather destination, I wear my winter coat on the plane and then store it overhead in a plastic dry-cleaning bag. (I try to wait until everyone is seated in my row — I always book an aisle seat — so I can make sure it’s lying neatly across the overhead luggage.)
Pack this essential for holiday shopping
If you’re heading to the European Christmas markets or even shopping extravaganzas stateside, you’ll want to make sure your fragile ornaments and holiday baubles get back in one piece. I pack bubble wrap for my ornaments (it’s lightweight) and even padded wine sleeves, which give me the chance to slide several things inside for protection. For items that aren’t breakable, I roll them in my clothes in my carry-on luggage and put the bubble-wrapped pieces in my personal item, like a backpack.
Send gifts to save time and space
Hopefully, by now you know not to pack wrapped presents in your carry-on. To save space and avoid any hassle with TSA, I send gifts ahead of time or buy them when I arrive.
Download the airline app
Even if you don’t regularly fly the airline you’ve booked for holiday travel, download its app on your phone. This way, you’ll get push notifications about delays or gate changes. It also makes it easier to rebook through the app if you face a cancellation. You can always remove the app after the flight.
Work all the angles when travel troubles arise
The words “delayed” or “canceled” can steal anyone’s holiday joy. The second I’m notified of a flight cancellation, I spring into action. I first call the airline and get on the app to reschedule my flight. Everyone rushes the airline desks for help, and I find this to be the fastest route. Knowing your flight options before you call can also help.
Also, keep in mind that if you didn’t book a flight or cruise directly through the airline, you may have to call the third party you booked with if your trip is canceled before travel begins.
This may sound neurotic, but I always have a backup travel plan in case of a cancellation. Before booking a flight, I look at backup flights and times, so I know my options for getting to or from my destination. I often book an airline that has the most flights out that day.
Also, educate yourself on the new rules about what airlines must pay or do in the event of long delays and cancellations. The laws differ by country. I keep all my receipts and travel information handy — from boarding passes to food receipts.
Buy the travel insurance
For years, I risked most trips without buying insurance. But after getting very sick in Croatia last year (even fearing I might end up in the hospital), I started buying trip insurance. Because I travel so much, I now even have a yearly membership with Allianz. My best advice before buying trip insurance is to read the fine print of what’s covered and what’s not, and decide what’s most important to you — from fully refunded trips to lost bags or medical coverage.
I always focus on the medical aspect, making sure I have the maximum coverage. My advice: when traveling abroad, go for a plan that offers $500,000 to $1 million in coverage for emergency transport. If you’re injured on a ski slope or face some other situation where you need to be airlifted to a hospital, this can come at a devastating cost.
This story was originally published October 31, 2025 at 11:54 PM.
