Why Most People Waste PTO (and don’t realize it)
Everyone agrees that vacations should be the most relaxing times in a calendar year. But, planning a good vacation where you are able to stress-free is one of the most difficult things to do. Just like in real estate and hand grenades, timing is everything when these trips. If you’re a full-time 9-5 worker like myself, planning trips around the 2026 Federal Holidays might be the way to go. The first thing I do each year is look to see what days holidays fall on. It’s easy to make those long weekends a day or so longer by bookending a PTO day with an observed holiday! If you utilize the holidays correctly you can maximize PTO this year and make this one of the best travel years recently! This guide breaks down the 2026 Federal Holiday Calendar and shows exactly how to turn limited PTO into extended time off.
2026 Federal Holiday Calendar
| Observed Holiday | Date Observed | Day of the Week |
| New Year’s Day | Jan 1 | Thursday |
| Martin Luther King Jr. Day | Jan 19 | Monday |
| Presidents’ Day | Feb 16 | Monday |
| Memorial Day | May 25 | Monday |
| Juneteenth | Jun 19 | Friday |
| Fourth of July | Jul 3 | Friday |
| Labor Day | Sept 7 | Monday |
| Columbus Day | Oct 12 | Monday |
| Veterans Day | Nov 11 | Wednesday |
| Thanksgiving Day | Nov 26 | Thursday |
| Christmas Day | Dec 25 | Friday |
These are the holidays we should be building our year around!
The PTO Stacking Strategy (How does this works for you!)
Now you can look at a chart and go don’t worry I’ll just piggy back off those dates and figure it out! Yes, that would work. The goal isn’t just longer weekends, it’s turning a small number of PTO days into extended strecthes off. I’m talking using 3 days to get 9(YOU READ IT RIGHT)! Nine days in a row potentially! But, I digress, the strategy here is trying to book end holidays and utilize PTO on both sides of the Holiday, that’s how you end up maximizing the PTO. Look for those midweek Holidays. Reason for that? Because then you end up getting 4-5 days off with mid-week travel to keep prices down! Now let’s see some real life examples here are my top 3 PTO stacking holidays for 2026.
Top 3 PTO Blocks for 2026
3. Fourth of July Use 4 PTO Days -> Get 9 Days Off–
First on the top three is a classic summer holiday. This year the Fourth of July is on a Saturday, so the observed holiday will be on Friday, July 3rd. July is a great time to take PTO because every is in summer mode and barely paying attention in the office anyway! The main reason I love this idea because you can take the 4 days leading up to holiday to get a full week off for it! That’s the kind of bang for your buck I like! Basically if you request 6/29-7/2 off you’ll be off celebrating America’s indepedence from 6/26 to 7/5!
2. Christmas to New Years Day Use 4 PTO days -> Get 10 Days Off –
If you’re traveling for the holidays every year, this might be your year! For 2026, Christmas Day and New Years Day 2027(I know let’s not get too ahead of ourselves) both land on a Friday. This helps us maximize every day we can at the end of the year! So if we take the days off between Christmas Day and New Years we’re only using a full 4 days and ending up with 10 days off! If you requested 12/28 to 12/31 off you’d be off from 12/25 to 1/3! Imagine showing up to work on January 4th knowing you missed all the annoying “see you next year comments” the previous week.
NUMBER 1: THANKSGIVING WEEK USE 3 PTO DAYS -> GET 9 OFF –
So this is my number one only for companies that give both Thanksgiving and the following days after. Many, but not all, companies do this, so double-check your calendar. Recently, the trend has been some companies giving off both Thanksgiving and the following day after which is huge when looking at maximizing PTO. There is no other week throughout the entire year where a company is giving you 2 days in a single week. Basically by taking three PTO days you get 11/21 through 11/29 off! Just in time to get back for the last day of November. Personally, I think this is the jackpot for PTO maxxing, but only if you’re company gives you that extra day. Otherwise I still do think it’s worth while to take that 11/27 day off as well if you’re company doesn’t give you off. But, if you don’t get that extra day, I think the Christmas break moves into number 1 spot on this list!
How I’m Personally Planning Trips Around PTO in 2026
Typically, each year I start by writing down how many days I have off and then marking down definite dates I will need to request off (examples: big birthdays, weddings, etc.) Because at the end of the day those days you can’t escape, you’re taking them no matter what. Then it’s time for the fun, playing around with the days left to see how I can maximize my time that my corporate email is on “Out of Office”.
This year I’m keying in on a few different holidays. Of course I’m looking at November and seeing Thanksgiving. One underrated PTO holiday that’s overlooked in November is Veterans’ Day! With Veterans’ Day being on a Wednesday this year we can take two days prior or after the holiday to get a full 5 days off in a row!
Another underrated PTO holiday the I’m keying in on this year is Juneteenth. I think it’s overlooked because it is a relatively newer Federally Recognized Holiday in PTO terms. I think if you take the four days in the week leading up to the Friday Juneteenth is on this year, we can get a full 9 days off. I like Juneteenth as a travel holiday because it will provide cheaper flights when compared to some of the more traditional holidays that schools have off such as Presidents’ Day and MLK Jr. Day.
If you’re a visual person like myself, utilize this PTO Calendar I created for 2026:
Tools & Resources I use to Travel Smarter
When I’m looking at these dates and have flexibility when traveling I like to look out a couple months and start seeing the price range for these trips. I’m personally a Marriott guy so I always go there first to see the Marriott’s in the area. But, Expedia is a solid option that gives you a bunch of different variety of hotels and rentals in the area. They also have a flight option so you can check that out as well! Also if you’re going away during popular date ranges you may have to look farther in advance for tours or things to do in the area. Personally, as soon as I book I start looking at Viator to see the different options in the area. I also peruse Viator prior to booking just to see the options of excursions in the area! One good example is what if you thought you were going to a city with a lot of culture and you check Viator and see zero options for museums or other guided historical tours? Then you might change that mind. So, I always recommend checking out Viator prior to booking anything to double check and make sure the theme of my trip matches the city. If you do need help making itineries or ensuring your trip matches the vibe you’re going for feel free to reach out to us at NBD Adventures!
Is PTO Maxing worth it?
Just like does an avid traveler have TSA Precheck? The answer is yes. With a little planning, PTO stops feeling limited and start feeling intentional and for 9-5 workers, that makes all the difference. I cannot stress how important this is enough, because as a 9-5 worker we need to take advantage of PTO and still see the world. If you need any help do feel free to reach out to our advisors here at NBD Adventures and we can point you in the right direction on when and how to take those PTO days this year and see the world!
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