Americans are determined to travel this holiday season — and certain workarounds are helping them take those trips. 

The ability to work remotely is a major leg up when planning out itineraries.

About 49% of employed travelers are “laptop luggers” — those who plan to work at some point on their holiday vacation — up from 34% last year, according to the Deloitte holiday travel survey.

This flexibility allows workers to take trips they might not otherwise, or stretch their trips for longer, according to the survey.

While there are more laptop luggers across most age groups and income levels, Gen Zers, which Deloitte defines as those born between 1997 and 2012, and high earners make up the highest shares, at 58% and 52%, respectively, according to the survey.

Deloitte polled 4,074 American adults in September. Of that group, 2,005 were identified as holiday travelers.

The change in laptop luggers is “a pretty high jump. It’s almost across all income levels and age groups,” said Eileen Crowley, vice chair and U.S. transportation, hospitality and services attest leader at Deloitte. 

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Since the pandemic, remote work has become a priority for job seekers, said Julia Pollak, chief economist at ZipRecruiter.

In the third quarter, 51% of surveyed job seekers said the ability to work from wherever they want is a top reason for remote jobs, up from 40.8% in the first quarter of 2022, according to ZipRecruiter data.

“The value to U.S. workers of being able to work from anywhere has clearly grown over the course of the great remote work experiment,” she said.

In addition to working during their trip, travelers are coming up with other workarounds such as driving instead of flying or cutting back on other expenses, experts said.

“People are willing to cut corners to save money, but they don’t want to skip the trip entirely,” said Ted Rossman, an industry analyst at Bankrate.

When it comes to holiday travel, 52% of shoppers with incomes of $100,000 or more said they can “easily afford” that expense, according to Morning Consult, a survey research firm. That is the highest share compared with mid- to low-income groups. 

“Higher-income consumers are not nearly as price sensitive,” Stacy Francis, president and CEO of Francis Financial, a wealth management, financial planning and divorce financial planning firm in New York City, recently told CNBC.

“They’re not nearly as budget conscious as people in lower-wage-earning brackets,” said Francis, a member of CNBC’s Financial Advisor Council.

Among generational groups, millennials, or those born between 1980 and 1996, have the highest budgets and longest travel planned. According to the report, millennials plan to take about 2.6 trips over the course of the holiday season and spend on average $3,927, per the Deloitte survey.

More than 4 in 5 holiday travelers, 83%, are finding ways to save money this holiday season, such as driving instead of flying, according to Bankrate.

“Most of these people are still traveling, they’re just doing so differently to cut some costs,” Rossman said.

Separately, about 50% of respondents are cutting back on other expenses and 49% are picking up discounts and deals, according to the 2024 Holiday Travel Outlook by Hopper, a travel site. 

Among other strategies, 22% plan to travel on off-peak days and 21% are using credit card points or miles to cover some of the cost, the Hopper report found.

If you do plan to pull out your laptop and work during a holiday vacation, make sure to review your company’s rules around remote work, said Pollak. Some companies require employees to work from their home, from within the company’s home state or within the U.S. unless otherwise authorized.

“You risk getting your access shut off, being punished or even having your employment terminated if you try to work from elsewhere,” Pollak said.

Touch base with your manager or director about the idea as well, she said: “Some managers just care that you’re getting the job done and aren’t concerned how.”

Finally, you want to make sure the location you plan to work from has a strong electric grid or service and Wi-Fi is reliable.

“If you’re on the hook for work, make sure you are somewhere where you can get it done,” Pollak said.

Spending on experiences such as travel and concerts spiked after pandemic-era lockdowns and restrictions because of pent-up demand from Americans, experts say.

Yet even after several years, travel “seems to be something that’s sticking,” said Deloitte’s Crowley: “People are placing value and making room in their budgets for travel.”

Typically, the five days beginning Thanksgiving Day and ending Cyber Monday are some of the busiest shopping days of the year.

This year, the number of people shopping in stores and online during that period could hit a new record, according to the National Retail Federation’s annual survey.

But consumers trying to make the most of the Black Friday sales may not be getting the best prices of the season.

According to WalletHub’s 2023 Best Things to Buy on Black Friday report, 35% of items at major retailers offered no savings compared with their pre-Black Friday prices. The site compared Black Friday advertisements against prices on Amazon earlier that fall. 

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“Some Black Friday deals are misleading as retailers may inflate original prices to make a deal look like a better value,” said consumer savings expert Andrea Woroch.

This year, in particular, some of the deals are already as good as they are going to get.

“Those holidays have gotten a little watered down because retailers want to maximize the selling days,” said Adam Davis, managing director at Wells Fargo Retail Finance.

“Compounding the importance of stretching the holiday season, retailers are facing a shorter selling season between Thanksgiving and Christmas — almost a week shorter in 2024,” he said. “That will force the retailer’s hand to be pretty promotional in November.”

DHL Supply Chain’s new CEO for North America, Patrick Kelleher, recently told CNBC that items may arrive later than in years past, especially those ordered around big dates such as Black Friday and Cyber Monday.

In a period of such high volume, third-party shippers are particularly strained, according to Lauren Beitelspacher, a professor of marketing at Babson College. An ongoing labor shortage also means that some companies simply cannot hire enough workers to sort, transport and deliver packages on time.

“We are very spoiled; we got to the point where we think of something we want and it magically appears,” Beitelspacher said. But at the same time, “we’ve learned how fragile the supply chain is.”

When there are more packages to ship, shipping times increase, which can also boost the chance they may get damaged, lost or stolen en route — not to mention the risk of “porch piracy” once an item is delivered.

For those planning a trip, “Travel Tuesday” is a good time to snag discounts on airfares, cruises and tour packages, with many hotels offering 20% to 30% off best available rates. Travelers can check out Travel Tuesday deals from 2023 to get an idea of what to expect this year.

With toys, it could pay to hold out until the last two weeks of December, and holiday decorations are cheaper the last few days before Christmas or right after, according to Woroch.

Exercise equipment, linens and bedding tend to be marked down more during January’s “white sales,” she said, and furniture and mattress deals are often better over other holiday weekends throughout the year, such as Presidents’ Day, Memorial Day and Labor Day weekends.

Despite a strong year for the stock market, you could still be sitting on portfolio losses. But you can leverage down assets to score a tax break, experts say.

The tactic, known as “tax-loss harvesting,” involves selling losing brokerage account assets to claim a loss. When you file your taxes, you can use those losses to offset portfolio gains. Once your investment losses exceed profits, you can use the excess to reduce regular income by up to $3,000 per year.

“Tax-loss harvesting is a tried and true strategy to lower investors’ tax bills,” said certified financial planner David Flores Wilson, managing partner at Sincerus Advisory in New York. 

After offsetting $3,000 in regular income, investors can carry any additional losses forward into future years to offset capital gains or income.

“Investors can benefit substantially over time” by tax-loss harvesting consistently throughout the year, Wilson said.

That’s because of guidelines from the IRS known as the “wash sale rule,” which blocks you from claiming the tax break on losses if you rebuy a “substantially identical” asset within the 30-day window before or after the sale.

In other words, you can’t sell a losing asset to claim a loss and then immediately repurchase the same investment. 

But ETFs with identical indexes, like the S&P 500, “will run afoul of the wash sale rule” and the loss won’t be allowed, Gagliardi said.

Ultimately, the IRS definition of “substantially identical” isn’t black and white and “depends on the facts and circumstances” of your case, according to the agency.

When in doubt, consider reviewing your plan with an advisor or tax professional to make sure you’re safe from violating the wash sale rule.