Your accumulated paid time off (PTO) represents valuable time that you can’t recuperate once it’s gone. In other words, you either use those days off, or lose ‘em.
According to a 2023 Pew Research Center American Trends Panel (a survey of U.S. public opinion research), 46 percent of U.S. workers who receive PTO from their employer take less than they’re offered (Americans working in private industry get an average of 11 vacation days after one year of work and an average of 15 days after five years of work, per the U.S. Bureau of Labor Statistics).
Whether for a family trip, a couples or friends getaway, or something solo and fabulous, why let the fruits of your hard work wither on the vine? When you know how to parlay your PTO into a prolonged getaway by padding it with federal holidays, you may be surprised how far those vacation days—and the extended quality time you have to truly immerse yourself in the experience—go.
“Time has become one of the most valuable luxuries in travel,” says Judy Perl, president of high-end travel consultancy Judy Perl Travel and a member of the Afar Travel Advisory Council.
“By stacking long weekends, shoulder seasons, and lesser-known destinations, you can often transform a relatively small number of vacation days into weeks of unhurried travel,” she says.
And when you go a step further by strategically visiting places most travelers aren’t visiting during that time of year, the payoff goes beyond more time on the ground.
These destinations have fewer crowds and greater value and seem more relaxed than the peak-season “usual suspects,” Perl says—and they likely appreciate your tourism dollars all the more, too.
Federal holidays are typically only one or two days, but by taking the remaining weekdays as vacation days, you can turn three or four days of PTO into nine days off when combined with weekends. Given that math, here are suggestions from Perl and other travel experts on how to make the most of some federal holidays this year (not including, for instance, Fourth of July, which falls in the middle of the busy summer travel season).
Fly to Fort Myers and drive to Sanibel Island in Florida for a much-needed February warm-up over President’s Day.
Photo by Melissa/Unsplash
Presidents’ Day: February 16, 2026
Lesser-known Caribbean islands
“Everyone dreams of trading bitter temperatures and gray skies for the warmth of the islands by Presidents’ Day, but not everyone wants to spend their vacation time fighting for beach chairs and tolerating slow service at overwhelmed resorts,” says Sheena Williams, a travel advisor with New York–based Embark Beyond. She recommends visiting less-trodden Caribbean islands like Montserrat and Dominica and lesser-known regions of the Turks and Caicos, such as Pine Cay, a private car-free island between Providenciales and North Caicos, and Ambergris Cay on the southeastern edge of the Caicos Islands; in the latter, look for passing humpback whales, as the February holiday coincides with their migration season.
Sanibel and Captiva Islands in southwest Florida
For a domestic warm-up in the U.S., Katy Nastro of Going says Sanibel and Captiva Islands are an hour’s drive from Southwest Florida International Airport (RSW) in Fort Myers, but “you may as well be on a tropical island thousands of miles away.” The islands are bike-friendly, you’ll be supporting local businesses that are still bouncing back after Hurricane Ian in 2022. Plus, February is one of the best times of the year for birding at Sanibel’s J.N. “Ding” Darling National Wildlife Refuge.
Go castle hopping in France’s Loire Valley in late May, around Memorial Day, before the peak summer crowds arrive, to access historic masterpieces like the striking Château de Chambord with fewer visitors.
Photo by Dorian Mongel/Unsplash
Memorial Day: May 25, 2026
Georgia and Croatia
Bolster Memorial Day week with some PTO days to get ahead of the crowds traveling to Europe for summer, says Perl. “It’s not peak season yet in Europe at that time of year. So you’re not battling crowds, you still have great weather, and all of the beach clubs are open by then.”
She points to Georgia and Croatia as great countries to target for quieter times before the summer surge.
France beyond Paris
Classic European destinations like France also shine at this time of year, adds Williams. “Enjoy vibrant spring blooms, serene city walks, incredible food, and smaller crowds in alternatives to Paris, like Bordeaux, the Loire Valley, and Lyon,” she suggests.
Early fall, like around Labor Day, is an ideal time to explore Waterton Lakes National Park in the Canadian Rockies before the colder months set in.
Christian_Phillips/Shutterstock
Labor Day: September 7, 2026
Naxos and Paros, Greece
“Greece is on everyone’s bucket list, but the summer months can be brutal, with hordes of people descending upon these islands at the same time as temperatures reach their peak,” Williams says, noting that early September is a perfect window for fewer crowds and milder weather. She and Perl both suggest bypassing places like Mykonos and Santorini, popular cruise-ship ports, in favor of lesser-visited Aegean islands like Naxos and Paros.
Alberta, Canada
In North America, Labor Day is a fine time to squeeze in a vacation up north before the seasons change, says Nastro, who suggests flying to Calgary, Alberta’s largest city, to explore the region.
“Tiny towns dot the southern Rockies, which can feel almost like an old movie set with single main streets, but this area is really for those looking to explore the outdoors,” she says, pointing to Pincher Creek and Sundre as great jumping-off points. Nastro suggests planning a cross-border road trip adventure between two national parks: Alberta’s Waterton Lakes National Park, a hiker’s wonderland webbed with waterfalls, and Glacier National Park are about an hour’s drive apart.
Head to Puerto Escondido on the Oaxacan coast in early November, perhaps over Veterans Day, right before the winter holiday crowds arrive.
Photo by Lorraine Mojica/Unsplash
Veterans Day: November 11, 2026
Oaxaca and surf towns, Mexico
Valleys are still verdant, but the rains have largely ceased in Oaxaca by October and November. And when you bank PTO days here for a trip leading up to or on the heels of Veterans Day, you can avoid peak Día de los Muertos crowds but still bask in the culture surrounding the revered Mexican holiday in the city best known for it.
With 17 rooms surrounding a jacaranda tree at the heart of the property, Hotel con Corazón invests profits in education programs for local adolescents. The hotel offers guests daily “Impact Tours” of small agave plantations, Indigenous Zapotec communities, and other places where tourism dollars benefit the locals.
November is a sweet season for visiting the Oaxacan coast, too, as the land is still lush from the rainy season and the holiday crowds have not yet arrived. It’s also a great time to visit beach towns like the surf-centric Puerto Escondido and Mazunte, one of the country’s “Pueblos Mágicos” (or “magic towns,” a designation given by the Mexican government for their beauty and historical or cultural significance), before peak winter-season crowds and snowbirds fly in.
In late November, you can get a sneak peek at charming Christmas markets like the one in Salzburg, Austria, which conveniently kicks off right before the Thanksgiving holiday.
Calin Stan/Shutterstock
Thanksgiving: November 26, 2026
Munich, Germany, and Salzburg, Austria
“Most of us forget that Thanksgiving is not widely celebrated around the world because it consumes our travel-planning thoughts,” says Nastro about Americans. But savvy travelers recognize this week as one of the best times to travel and stretch their PTO (especially if your employer automatically makes it a four-day weekend).
The week of Thanksgiving is a great time to take advantage of affordable airfare and seasonal fun outside the U.S., Nastro says, with European cities like Salzburg and Munich entering Christmas-market mode. “Average flight prices into Munich can sit between $800 and $1,000, but with so much less international demand during the Thanksgiving week, we often find flights between $360 and $589 round-trip [from the U.S.],” she says.
Peru
Perl points to Peru as a perfect destination in the Americas during Thanksgiving week, since it falls right before the rainy season goes full tilt. This shoulder season is perfect for a crowd-free trip to places like Machu Picchu and for misty views of the cloud forest at remote eco-lodge Gocta Natura Reserve, a Certified B Corporation in Northern Peru’s Amazonas region known for hiking and bird-watching.
