How to Maximize Your PTO in 2026 – And Where to Spend it
New year scaries? No problem. If you’ve found yourself counting down the days until your next PTO, you’re not alone. Lucky for you, though, there are several ways to maximize your PTO in 2026, and fabulous places to spend it. So, grab your calendar, credit card and pull up that request form – let’s plan a trip (or a few) for 2026.
In This Article
Jan. 16-19, 2026
Observed Holiday: Martin Luther King, Jr. Day
PTO required: 1 day
Total days off: 4
Where to go: Memphis, Tennessee
The third Monday in January commemorates Civil Rights activist Martin Luther King Jr.’s birthday, so what better way to celebrate than with a trip to Memphis, TN? Home to the National Civil Rights Museum and the Lorraine Motel, where King spent his final hours before his death, Memphis is a hub for history, culture and innovation.
Historic Beale Street houses everything from blues and barbecue to museums and music. Listen to live performances at B.B. King’s Blues Club, savor fall-off-the-bone, Bobby Flay-approved ribs at Blues City Cafe, flip through vintage Sun Records at Memphis Music, stroll by Overton Park Shell, where Elvis Presley gave his first paid concert. Speaking of Elvis Presley, you can take a tour of his legendary Graceland while you’re in Memphis. Step inside the gates and see original artifacts, including his pink Cadillac and dazzling performance costumes. But don’t forget to stop at the Withers Collection Museum & Gallery. Featuring the work of acclaimed photojournalist Ernest Withers Sr., the gallery is full of images taken at the height of the Civil Rights movement.
Feb. 13-16, 2026
Observed Holiday: Presidents’ Day
PTO required: 1 day
Total days off: 4
Where to go: Charleston, South Carolina
President’s Day, falling two days after Valentine’s Day, creates the perfect opportunity to enjoy a long weekend with your special someone or friends. Pack your bags and head to the charming Charleston, SC. Bursting with beautiful architecture, scenic sites and plenty of food and shopping, it’s an ideal getaway for lovers and friends alike.
Visiting here during the off-season has plenty of perks, including milder temperatures, fewer crowds and lower travel rates. Cozy up for a horse-drawn carriage or harbor cruise tour through downtown. Explore Charleston City Market, King Street and Waterfront Park. Wet your whistle at Graft Wine Shop & Wine Bar, Prohibition or The Gin Joint. And don’t forget to grab a Michelin-recommended meal at Sorelle (Italian), Leon’s Oyster Shop (seafood) or Lewis Barbecue.
May 22-25, 2026
Observed Holiday: Memorial Day
PTO required: 1 day
Total days off: 4
Where to go: South Padre Island, Texas
Everything is bigger in Texas, including the beaches. A 34-mile-long oasis, South Padre Island is only a portion of the larger Padre Island, the longest barrier island in the world. The month of May here brings the perfect early summer temperatures, with highs reaching about 70 to mid-80 degrees.
While South Padre Island has plenty of your standard beach activities, there are also some with a Texas-style twist. Enjoy horseback riding on the beach, sea turtle trails and even whale watching.
The island is also home to a variety of shops, restaurants and live music venues. Art Sea and Gallery Goods carries everything from jewelry to pottery, so you’re bound to find something to take home. Viva restaurant offers stunning waterfront views and mouthwatering tacos. And if you’re looking for a little late-night fun, sip on a cocktail and listen to live music at places like Lobo Del Mar Cafe, The Rockin’ Cigar Bar & Grill, and Coral Reef Lounge.
June 18-21, 2026
Observed Holiday: Juneteenth
PTO required: 1 day
Total days off: 4
Where to go: Buffalo, New York
Did you know that Buffalo, NY, has one of the longest-running Juneteenth festivals in the country? Celebrating 50 years in 2026, this large-scale event commemorates the end of slavery in the United States, as well as the many contributions of African American and Black Americans of the past and present. In addition to a parade, attendees can expect loads of cultural gems, ranging from handmade jewelry and made-from-scratch delicacies to live music of every genre and dance performances.
But how would you spend the rest of the weekend, you ask? Luckily, Buffalo is a short drive from several towns and treasures perfect for exploring. Discover the origins of the Arts and Crafts Movement in East Aurora, shop, sip, and savor on historic Main Street in Williamsville, sample beer, wine, and bourbon in Hamburg or see the “Grand Canyon of the East” at Letchworth State Park.
July 2-5, 2026
Observed Holiday: Independence Day
PTO required: 2 days
Total days off: 4
Where to go: Boston, Massachusetts
Boston on the 4th of July? Revolutionary! Kick off Independence Day in the place where it all began. In addition to the annual Boston Pops Firework Spectacular, Boston is hosting a variety of patriotic celebrations across the city this year in honor of America’s 250th anniversary, including Sail250 and special exhibits at the Museum of Fine Arts.
During your stay, be sure to check out city staples like Boston Common, Fenway Park, Boston Tea Party Ships and Museum, New England Aquarium, The Paul Revere House and the John F. Kennedy Presidential Library.
And it wouldn’t be a trip to New England without some caffeine and crustaceans. Get your coffee fix at Phin Coffee House, Polcari’s Coffee or the “Friends” themed Central Perk Coffee Co. Then, chow down on fresh lobster, crab, oysters and more at Boston Sail Loft, Ostra and Red’s Best Fish Market.
Sept. 4-7, 2026
Observed Holiday: Labor Day
PTO required: 1 day
Total days off: 4
Where to go: Chicago, Illinois
Looking for pleasant weather, lots to do and plenty of fun? Welcome to Labor Day weekend in Chicago, where the river, drinks and good times are always flowing. The free Labor Day parade takes place in the city’s historic Pullman district, and features live music, community floats, and plenty to eat, drink and do.
But there’s plenty more fun to be had throughout the Windy City. Stroll along the Chicago Riverwalk, explore the Art Institute of Chicago, see Wrigley Field and Cloud Gate, take an architecture or mobster tour, eat a hot dog at Portillo’s, grab a slice of deep dish at Giordano’s Pizza and then top it all off with a sweet treat from The Original Rainbow Cone.
Nov. 11-15, 2026
Observed Holiday: Veterans Day
PTO required: 2 days
Total days off: 5
Where to go: Richmond, Virginia
November is the perfect time to explore Richmond, VA. The state’s foliage hasn’t completely faded, the temperatures are cool enough to bundle up (and not freeze) and, most importantly, there’s plenty to do as the state transitions from fall to winter.
Free art can be found all around the city – literally. The prestigious Virginia Museum of Fine Arts doesn’t charge admission, and the town is adorned with murals and street art. Richmond is full of history, too – making it the perfect place to spend Veteran’s Day. Serving as the Confederate Capitol during the Civil War, you can learn more about its role during this pivotal time in American history at places like the Virginia State Capitol, American Civil War Museum, Black History Museum and Cultural Center of Virginia and the White House of the Confederacy.
Richmond is also known for its diverse culinary and spirit scene. Enjoy everything from Southern-style barbecue to locally crafted beer at places like Mama J’s Kitchen and The Veil Room Brewing Co.
Nov. 25-29, 2026
Observed Holiday: Thanksgiving
PTO required: 2 days
Total days off: 5
Where to go: New York, New York
Nothing says Thanksgiving quite like the iconic Macy’s Thanksgiving Day Parade in New York City. Though this trip may require some extra planning and saving, we assure you the experience is worth it. So, set your alarm extra early and bundle up to go snag your perfect spot for the biggest parade of the year.
While you’re there, be sure to visit the city’s most iconic sites, including Rockefeller Center and its famous Christmas tree, Times Square, Washington Square Park, The Empire State Building, St. Patrick’s Cathedral and the Museum of Metropolitan Art.
Looking to do some holiday shopping? There’s no better place to spend Black Friday than the city that never sleeps. Head to Brooklyn and find everything from vintage jackets and bags to trendy sweatshirts and trinkets at places like Mirth Vintage, Seven Wonders Collective, From Here to Sunday and Leroy’s Place. Top it all off with a slice of New York-style Pizza at Mamma’s TOO, John’s of Bleecker Street or Chrissy’s Pizza.
Dec. 24-27, 2026
Observed Holiday: Christmas Eve & Christmas Day
PTO required: 1 day
Total days off: 4
Where to go: Bethlehem, Pennsylvania
Christmas City? Yes, please! No matter how you celebrate the holidays, being surrounded by cozy weather, twinkling lights and a downtown out of a Hallmark movie sounds pretty great, right? Bethlehem, PA, offers just that. Commonly referred to as “Christmas City,” they take their holiday roots quite seriously. The city itself was founded on Christmas Eve 1741, so it’s only fitting that it feels extra festive this time of year.
Visitors can enjoy holiday-themed activities such as the Christkindlmarkt, Christmas pub tours, Christmas City Village, horse-drawn carriage rides throughout the city and, of course, plenty of light displays. You can also shop in the oldest bookstore in the United States, Moravian Book Shop, explore Lost River Caverns or learn more about the city’s industrial roots at SteelStacks and the National Museum of Industrial History.
Dec. 30, 2026-Jan. 3, 2027
Observed Holiday: New Year’s Eve & New Year’s Day
PTO required: 2 days
Total days off: 5
Where to go: Nashville, Tennessee
Broadway, biscuits and big names – oh my! Pack your bags and get ready to ring in the New Year in Music City, better known as Nashville, TN. Their annual New Year’s Eve event, New Year’s Eve Live: Nashville’s Big Bash, is something everyone should experience at least once. And even better? Admission is free. Enjoy food trucks full of local favorites like barbecue, hot chicken and tacos. Sip on craft beer, sweet tea or Tennessee Whiskey. Then, rock in the new year with some of country music’s biggest names. Past performers include superstars such as Lainey Wilson, Jelly Roll, Shaboozey, Kelsea Ballerini and Kane Brown.
Nashville’s known for more than just music, though – particularly, its booming culinary, entertainment and shopping scene. Try the menu of a James Beard Award-winning chef at Peninsula, grab a fresh Pain Au Chocolat from D’Andrews Bakery or a heaping plate of fried chicken and waffles at The Loveless Cafe. Shop for everything from jackets and boots to souvenirs and baked goods at L&L Market and 5th + Broadway. Last, but certainly not least, be sure to visit the infamous Lower Broadway to experience celebrity-owned honky tonks, the National Museum of African American Music, and the Mother Church, Ryman Auditorium.
