For workers and students across the United States, the end of the year brings a much-anticipated stretch of holidays, school breaks, and—if you play your cards right—a chance to make your paid time off (PTO) go a very long way. Whether you’re dreaming of sun-soaked beaches or simply a few more days to sleep in, smart planning around federal holidays and school closures can turn just a couple of weeks of PTO into over 50 days away from the daily grind.
Let’s start with the basics: the calendar for 2025 and 2026 is packed with opportunities to maximize your time off, especially if you’re strategic about combining weekends, public holidays, and your limited PTO. According to Majic 94.5, by stacking holidays, weekends, and a handful of PTO days, you can enjoy more long weekends and mini-vacations throughout the year—without burning through your entire PTO balance.
Here’s how the math works out. In January 2026, New Year’s Day falls on a Thursday. If you decide to take off Friday, January 2, you’ll score a four-day weekend right out of the gate. Just a couple of weeks later, Martin Luther King Jr. Day lands on Monday, January 19. By requesting Friday, January 16 as PTO, you’re looking at another four-day stretch of freedom.
February brings Presidents’ Day on Monday, February 16. Take off Friday the 13th (which, incidentally, is also the day before Valentine’s Day), and you’ve got a perfect setup for a romantic getaway or a simple escape from routine. According to Majic 94.5, these well-timed requests can transform the winter months into a series of rejuvenating breaks.
Fast-forward to May, and Memorial Day falls on Monday, May 25. Taking Friday, May 22 as a PTO day means yet another four-day weekend. And for those whose employers recognize Juneteenth, which falls on Friday, June 19, requesting Monday, June 22 off creates still another four-day opportunity for rest or travel.
The summer doesn’t disappoint either. Independence Day in 2026 is on Saturday, July 4. By taking off Friday, July 3 and Monday, July 6, you can enjoy a rare four-day weekend in the heart of summer. Labor Day in September is another easy win: it lands on Monday, September 7, so a PTO day on Friday, September 4 extends your break once again.
October’s Indigenous Peoples Day (Monday, October 12) is observed in some workplaces. If you’re among the lucky ones, take off Friday, October 9, and voilà—another four-day weekend. November brings the possibility of an even longer break. Veterans Day falls on Wednesday, November 11; if you take off Thursday and Friday, you’re staring down the barrel of a five-day vacation.
Thanksgiving in 2026 is set for Thursday, November 26. If your workplace also gives you Friday off, adding Monday, November 30 as PTO means you’ll enjoy a five-day holiday—perfect for travel, family, or simply catching up on sleep. And then comes the grand finale: December. By taking off December 21-23 and December 28-31, you’ll string together a whopping 13-day break, including New Year’s Day on Friday, January 1, 2027. That’s more than two weeks away from work to close out the year and start the next one refreshed.
But it’s not just working adults who benefit from a well-planned calendar. Students and families in Florida, for example, are looking forward to a winter break that’s longer than most. As reported by the Naples Daily News, most Florida schools begin their winter break on Monday, December 22, 2025, with students returning to classrooms between January 5 and January 8, 2026, depending on the county.
Collier County Public Schools, in particular, are giving students a generous break. Their last day of classes is Friday, December 19, 2025, with winter break officially starting on Saturday, December 20. Teachers will return on Monday, January 5, but students get an extra day, returning only on Tuesday, January 6. That’s more than two full weeks off for Collier County students—plenty of time for family trips, holiday celebrations, or just unwinding.
The state of Florida also recognizes Christmas Day (Thursday, December 25) as a paid holiday, along with the day after Christmas (Friday, December 26) for state employees. This tradition, bolstered by a recent move from Governor Ron DeSantis to add extra holidays for state workers, ensures that many Floridians will have a little more time to relax around the holidays.
After winter break, the next major school holiday across all Florida counties is Martin Luther King Jr. Day on Monday, January 19, 2026—a day off for students and a chance for families to extend their break just a bit further. Other key dates on the Florida school calendar for 2026 include Presidents’ Day on Monday, February 16, Spring Break from March 6 to March 13, Good Friday on April 3, and Memorial Day on Monday, May 25. The last day of school is set for May 28, 2026, with an early dismissal to kick off summer vacation.
Of course, the exact timing of school breaks varies by district. Some districts wrap up before Christmas, while others start their break closer to the holiday itself. Return dates also range from January 5 to January 8, as local school boards set their own calendars. According to the Naples Daily News, this flexibility allows districts to meet local needs but can make it tricky for parents with children in multiple counties.
For those who want to keep track, here’s a quick snapshot of key Florida school break dates for winter 2025-2026: Alachua and Baker counties start break on December 22 and return on January 6; Brevard and Broward return on January 5 or 6; Collier, Charlotte, Citrus, and many others resume classes between January 6 and January 7. The details can get complicated, but the bottom line is clear: most Florida students will enjoy a substantial holiday break this year.
So, what’s the secret to making the most of your time off? It’s all about planning ahead. By leveraging federal holidays, school breaks, and a handful of PTO days, you can transform the calendar into a series of restful escapes and cherished memories. Whether you’re a working adult or a student, the coming year offers plenty of chances to recharge—if you know how to spot them.
With a little foresight and some strategic requests, you can turn the standard calendar into your own personal playground of long weekends, mini-vacations, and extended holidays. Now’s the time to check your PTO balance, grab a calendar, and start planning for the year ahead—because those perfect getaways won’t plan themselves.