The Holidays Are Longer Now. Is That a Good Thing?

Thanksgiving was a holiday that used to feel rushed for Molly Himmelstein Hollenberg. Chained to desk jobs in New York City, first at the “Today” show and then JetBlue, she used to fly to Memphis, her hometown, Wednesday to Sunday to see her parents. “I was working in an office, and I only had so many vacation days,” she said.

The first two days were spent cooking and eating. By the time the holiday was over she had only two days left to relax before battling crowds at the airport again.

“The trip was always way too fast,” she said. But not anymore.

Like many Americans, Ms. Hollenberg, 33, who now works for American Express as a product manager, has the ability to work remotely.

This year she flew to Memphis the Saturday before Thanksgiving and is staying until Dec. 2, eight days after the main event. She will work from her childhood bedroom and spend her free time with friends and family.

Her holiday felt more leisurely the second she boarded her Saturday evening flight. “There were no delays, it wasn’t full, it was a very comfortable experience,” she said. Plus, it was one of the cheapest flights she’s ever bought for this time of year. “Flights are so expensive around the holidays,” she said. “Being able to extend your trip for a few days on either side allows you to book a cheaper flight and not be in the airport on the busiest day of the year.”

“This year I can finally make Thanksgiving what I want it to be,” she added.

This year for some who are able to work remotely, Thanksgiving plans and Christmas trips with family members are being extended. According to Skyscanner, the travel search engine, it is more popular this year to travel Friday, Nov. 18 (the weekend before Thanksgiving) than Wednesday, Nov. 23 (the day before Thanksgiving.) Skiplagged, another search engine for flights and hotels, is seeing similar trends for Christmas. The company said on average Christmas trips are 26 percent longer in 2022 than 2021, which equals two extra days.

At the Skift Aviation Forum American held in the middle of November, American Airlines CEO Robert Isom told the audience that stressful peak travel days around the holidays may be a thing of the past. “We’re seeing demand is more spread out,” he said. “Travel, as it’s come back, we’re doing things differently.” A Delta Airlines representative confirmed that its peak travel day before Thanksgiving this year was the Friday before the holiday.

But more family time can also pose its own challenges.

“It will be nice to have everyone together for a while, but I think it might be a little chaotic,” said Carol Himmelstein, 65, Ms. Hollenberg’s mother who is hosting all her children in her home. “There are two bathrooms upstairs and eight people will be using them.”

“A friend of mine said she has a spreadsheet for all the meals,” Ms. Himmelstein said. “We don’t have that. We are going to wing it.”

For Jessica Giles, 36, editor of Cosmopolitan, she didn’t even know if she could attend Thanksgiving this year at her dad and step-dad’s home in Plain City, Ohio, if she couldn’t work remotely and stay for a week.

“We got a pandemic dog, a rambunctious mix, who can’t fly and must drive,” she said. The trip from New York City, where she lives, takes two days in each direction.

“We are going antiquing, and they are on a little farm and we will take walks through the woods and cook some dinners,” she said. “The forecast seems to be a much more relaxing trip than we were ever able to have.”

Thomas Giordonello, 33, a cannabis publicist who lives in Los Angeles, works for himself and always had the ability to work from home. But he never even thought about extending his holiday before the pandemic.

“I used to fly in Tuesday, fly out Black Friday when all the other people were out hunting for deals,” he said. “I did it every year.”

But celebrating the holidays remotely during the pandemic made him realize there was not a set way to do things. This year he decided it was important to spend quality time both with his father, who lives alone in Garrison, N.Y., and his sister, who recently bought a house nearby. “Our mom passed away, so I want to do things with her that our mom would have done,” Mr. Giordonello said.

He arrived in the Northeast the Tuesday before Thanksgiving and will stay with his father for two weeks. “The thing about going home is in theory it’s fabulous, it’s restorative, it’s grounding,” he said. “But I can’t forget that after a week of being home in my childhood room I am going to argue with my dad about leaving coffee on the pot too long.”

He hopes this stay will inspire his family to celebrate the holidays more creatively in the future. “I’m working on my dad and sister to see if they want to go to Big Bear and get a cabin for Christmas,” he said, referring to the resort city in Southern California. “We’re in this weird transitional moment.”

For Eric Sedransk, spending only a few days with his mother in Hilton Head, S.C., over Thanksgiving would feel strange since he lived with her for six months during the pandemic. “The whole paradigm has shifted where you naturally expect to stay longer now,” he said. “That length becomes the new normal.”

He can’t even fathom what he used to do for the holidays. “I had a job where I had to be in an office, so I was always trying to think about how I could get a direct flight, and how I could get home and back without an absolute disaster,” he said. “The holiday always felt like it was too expensive, too rushed and too stressful.”

Now Mr. Sedransk, 38, who lives in Bend, Ore., and runs Member for a Day, a charity platform where organizations auction off golf experiences, is spending at least two months with his mom. He arrived before Thanksgiving and was planning on staying after Christmas.

They are still planning on doing all their holiday traditions including “making the biggest bowl of mashed potatoes on Earth,” he said. But he isn’t sure if the actual holiday will feel as special because his trip is so long. “The actual day of Thanksgiving, because I’ve already spent two weeks with my mom in advance, might not be the same,” he said.

But it is a small price to pay for all the quality time they are getting together.

“In the past we used to see our parents for maybe three days at Thanksgiving and five days at Christmas and maybe a wedding now and then,” Mr. Sedransk said. “All of that is changing. My mom and I have gone for a long walk on the beach almost every day.”

He added, laughing, “I don’t even have a flight out yet.”