There are 11 federal holidays in 2026, and if you’re one of the lucky Americans with paid time off, a little strategy can turn those fixed dates into something more generous. You can take long weekends that actually feel long and four-day breaks that cost only one vacation day.
Every year, this brand of calendar “hacking” makes the rounds on social media, and websites like Holiday Optimizer have popped up to help travelers capitalize on the concept.
Laura Carden-Lovell, head of operations at Transfer Travel, says the trend reflects how Americans use their time off. Vacation days in the United States are uneven and often scarce, and “that constraint is reflected in how trips are planned,” Carden-Lovell said in an email.
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“On Transfer Travel, we see this reflected in higher demand for short stays, increased interest in trips tied to long weekends, and a growing preference for closer-to-home destinations that don’t require extensive time off,” she added.
Tammy O’Hara, owner of the agency Million Miles Travel, said her clients range in PTO availability from scant to unlimited. However, no matter how much they’re allotted, she said, most find it difficult to pry themselves away for a vacation.
“That’s where I think maximizing the use of holidays helps because it alleviates some of the ‘guilt’ of being on vacation during working hours,” she said.
Of course, this method isn’t rocket science, and the concept has been around longer than the advent of Instagram. It also won’t work for everybody. Plenty of people in health care, hospitality and retail are required to work holidays. Parents often end up using precious PTO when their kids get sick. Many jobs (like teaching) have “blackout days” around holidays that don’t allow for taking more time off.
One last caveat: Just because these are the best days off to maximize your PTO doesn’t mean it’s necessarily the best time to travel. Flights, hotels and cruises are often more expensive around holidays, when demand is high. O’Hara said three-day weekends are some of her most requested periods to book vacations.
“My advice is always to plan ahead to get the most out of your dollar,” she said. “So I am looking at holidays now in the second half of the year such as Labor Day.”
Here’s a guide to help jump-start your strategizing.
Elongate winter weekends
When the Christmas tree has hit the sidewalk and your dopamine could use a midwinter boost, tack on a couple days to the three-day weekends in January and February.
Angie Licea, president of the Global Travel Collection, said these early holidays see strong demand to the Caribbean and South America.
For New Year’s Day, you could take off Friday or Monday, or both, to recover after the holiday. For Martin Luther King Jr. Day on Jan. 19, take off the preceding Thursday and Friday for a five-day vacation or just Jan. 20 for a four-day weekend. The same advice goes for Feb. 16, which is Presidents’ Day.
The latter overlaps with one of the year’s biggest sporting events, the Winter Olympics in Italy (Feb. 6 through Feb. 22).
Royal Ahmadi, senior vice president of the Vacation Group, says that 2026 will be a huge year for sports tourism, and that events like the Olympics and the FIFA World Cup (June 11 through July 19) will be “major motivators” for travel planning.
Splurge on spring
Memorial Day — May 25 — is the only spring holiday on the federal calendar. Carden-Lovell recommends splurging on time off, taking advantage of shoulder season’s lower prices, thinner crowds and cooler temperatures (outside spring break periods, of course).
Travel agent Kristal Hicks also believes Memorial Day is “significantly underutilized,” she said. “It’s the beginning of summer but not quite peak season yet, which often means better availability and value — especially for Europe.”
You can turn four PTO days into a nine-day break around the Memorial Day holiday by requesting off May 26 through May 29.
Stretch summer breaks
There are three federal holidays to factor into your summer vacation plans:
- Juneteenth on June 19, which is a Friday.
- Independence Day on July 4, which falls on a Saturday, so the federal holiday gets shifted a day earlier to July 3.
- Labor Day on Sept. 7.
You can bookend any of the holidays to make room for five-day trips, or take the rest of the week off to yield a nine-day break from four PTO days.
Or for a longer trip, Heather Wassel, a travel designer who specializes in luxury Europe trips, recommends a trip that takes advantage of both Juneteenth and July 3. For nine days of PTO, you can get a 17-day block.
Carve out fall getaways
After the busy summer season, fall is a quieter time for travel, making it a good time for deals.
Request Oct. 9 off to turn Columbus Day (Oct. 12) into a four-day weekend — just enough for a peak fall getaway. Play around with Veterans Day (Nov. 11), a midweek holiday. You can take either Nov. 9 and 10 or Nov. 12 and 13 for a five-day break on two PTO days — a treat before the hectic holidays.
Add buffers to the holidays
Thanksgiving week is one of the best times of year to find cheap flights abroad. Request off Nov. 25 and Nov. 27, to get a five-day window for an international jaunt.
Christmas falls on a Friday in 2026, giving you a three-day weekend to work with already. Take off Dec. 24 and Dec. 28, and two vacation days turns into a five-day break.
Still have PTO to spare? Take off Dec. 28 through Dec. 31 and you’ll have 10 straight days off because New Year’s Day is a Friday in 2027.
Want to spend that time on the high seas? Ahmadi says that over Thanksgiving and Christmas, cruise lines “often offer excellent pricing and promotions … when booked well in advance.”
The post How to get the most days off with your vacation time in 2026 appeared first on Washington Post.
