9 expert holiday travel hacks for a stress-free trip

Holiday travel is never simple for any of us. But for me, it’s extra complicated: I was a digital nomad for three years—bouncing from Cambodia to Colombia, Morocco to Malta, Iceland to Israel—which meant that during the winter holidays, when back in the U.S., I needed to see as many people as possible and make up for lost time. Bonus complications? My parents are divorced and my friends are scattered across the country, so holiday travel demands careful planning, ingenuity, spreadsheets—and luck. But it can be done. This is how to hack it.

Maximize flexibility, minimize frenzy

Let data guide your scheduling. “The Sunday after Thanksgiving is one of the worst days to fly,” says Sally French, travel expert from Nerd Wallet. I do whatever I can to dodge frenzied (and pricier) travel days, and the key is to maximize flexibility. For those on a typical nine-to-five schedule, this could mean strategically burning some PTO—such as the Monday after Thanksgiving or the few days between Christmas and New Year’s.

This year, aim to fly out on Friday December 22 (giving you some margin for error), return on Tuesday January 2, take just three days as vacation (December 22, 26 and 27), and if you can swing it, book into a quiet coworking spot and WFV (that’s Working From Vacation) for the rest. That gives you a 12-day block away, including weekends. (Can’t leave the cat that long? Fly back on Friday December 29 and have the long weekend at home to recuperate, and you still juke the craziest travel days.)

“Redefine what holiday travel looks like for you,” says travel writer Kiki Rich, aka The Blonde Abroad. If you’re tired of the holiday status quo, she says, “Initiate the conversation to think outside the box.”

Score points with points

What if buying your parents gifts can help pay for your ticket home? In Expedia’s One Key loyalty program, you can rack up rewards when buying experiences (such as a foodie tour in your family’s hometown), and then the OneKeyCash earned from those goodies can be used on future flights, hotel bookings, and more. Then there’s a sneaky extra bonus. “You still get airline miles,” says David Slotnick at The Points Guy. He explains that because you can earn rewards with both Expedia and the airline, you can spend once and earn twice.

Go airport shopping

When I’m flying to LA to visit family, I consider not just LAX and the almost-as-obvious John Wayne and Burbank, but also San Diego (just a quick train ride away) and even San Francisco, San Jose, and Oakland, where I could first visit friends in the Bay Area. This adds more flexibility, boosting the chance of lower fares. If your destination is inflexible? Odds are you have wiggle room in the connecting airports. Choose wisely. When Nerd Wallet’s Sally French travels to St. Louis to visit her mom, her layover options include both LA and Chicago. “Nobody can predict the future,” says French. “But in general, avoid the airport that’s more likely to get a snowstorm.” (Sorry, Chicago.)

Build in the buffers

Over-scheduling is the hobgoblin of holiday travel. Be kind to yourself. Be kind to your hosts. Add in some buffer days with absolutely nothing planned, so if your flight is delayed or canceled (it happens) your entire trip is not scuttled. The first year I traveled to New York in December to visit old friends, I created a spreadsheet that optimized every day for social lunches, dinners, and drinks. That wasn’t sustainable. I now include cushion days to relax and recharge, which keeps me looking forward to the next trip.

Then there’s the most important buffer of all—the mental buffer. Expect that things will go wrong. Make peace with it. Lost luggage will be found, delayed flights will arrive, and the traffic delaying your cab will eventually clear. View the trip through a wider lens. The best holiday gift of all is being able to travel and roam and see our favorite people—so let’s embrace it.

Book early

“We’re all at the mercy of computers and algorithms these days,” says Chelsea Dickenson, aka Cheap Holiday Expert, as the prices of flights will inexorably climb as the holidays approach. So commit ASAP. Even if you’re not certain of your exact travel days, says Dickenson, “Book a flexible ticket that allows you to cancel.” Or if you truly need more time to decide, Expedia’s Price Tracking tool can let you swoop in and buy if and when the fare drops.

The trick to holiday packing

I never bring gifts with me. Instead, I let the post office be my elves: I order online and have gifts shipped directly to my destination, which helps me avoid checking luggage. (Bonus tip to the bonus tip: Address the packages to yourself; this way your host doesn’t open them by mistake, and you can personally gift-wrap once you arrive.)

For family face-offs, stick to an objective code

Instead of trying to visit every contingent of your family (such as divorced parents or in-laws), stick to a hard rule of “every other year.” There are no bruised feelings if you can point to a clear and fair plan: I’ve done this for over 20 years and I’ll do it for over 20 more.

Consider the less obvious destination

If you opt to travel somewhere as a family, avoid the usual suspects. “You’re not the only one who wants to go to Cancun,” says Matt Kepnes, aka budget travel blogger Nomadic Matt. “Finding alternative destinations with the same climate will help you save money.” Instead of Playa del Carmen, consider Sayulita. Less Cancun, more Nicaragua. “Zig when everyone zags,” he adds. “There are always deals. You just have to look for them.” (Tip: start here.)