It’s probably no surprise that I vacation more than most people I know. I often get questions about how I can afford the vacations and how I have so much time off from work.  I have written tons about how I  use points and miles to “pay” for the bulk of my vacation costs, and you can learn all about how I Travel Hack. 

This article is about how I strategically use PTO to maximize my days off work.  My company does not follow the standard federal/bank holidays calendar, but I will focus this article on that standard calendar because it applies to most people.

Knowing when to take days off can make a big difference if you want to get the most out of your paid time off in 2025. By planning to take PTO around key holidays and weekends, anyone can stretch a few days of paid time off into several weeks of vacation. This approach helps you enjoy longer breaks without using up all your valuable PTO.

When to Take PTO to Maximize Vacation: Tips for Longer Breaks and Smart Planning

Some times of the year are better for PTO because they include public holidays or long weekends. For example, taking a few days off around President’s Day in February or the holidays at the end of the year can give you more days away from work for the same amount of PTO.

I’ve found that knowing these dates early lets me plan trips well in advance. I start planning our family vacations a full year in advance.  I have two kids in school and have to plan around their school calendar, as well as mine and my husband’s work calendar.   

Making your vacation time stretch means you don’t pick random days. It’s about using your PTO strategically by combining it with weekends and holidays to get the most time off. Keep reading if you want specific tips on when to book your time off to maximize your breaks.

Key US Holidays To Target

Knowing the right holidays to plan around helps me get the most days off with fewer PTO days. To stretch your time off, focus on days that fall close to weekends or other holidays.

Federal Holidays Overview

I am writing this article in 2025, and there are 11 federal holidays when most offices, schools, and government buildings close. These are your first chances to save PTO days because they automatically give you a day off.

These holidays include familiar ones like New Year’s Day, Independence Day, and Christmas Day. Some fall on fixed dates, while others shift depending on the week.

By targeting these official holidays, you can build vacation time around them. For example, when a holiday falls on a Friday or Monday, everyone gets a natural long weekend without using PTO. Add a day or two of PTO to the start or end of that long holiday weekend, and you end up with enough time to take a real vacation.

Here are some key holidays to think about every year:

• New Year’s Day
• Martin Luther King Day
• Presidents Day
• Good Friday
• Memorial Day
• Juneteenth National Independence Day
• Independence Day
• Labor Day
• Columbus Day
• Veterans Day
• Thanksgiving
• Christmas Day

Knowing these exact federal holiday dates in advance helps you plan when to schedule your PTO around them. For example, in 2025, taking PTO on Thursday, July 3, creates a four-day weekend, plenty of time to celebrate or take a trip.

Long Weekends In 2025

Long weekends are your best friend when it comes to stretching PTO. Every year many federal holidays fall on Fridays or Mondays, making it easy to get at least a four-day weekend with just 1 day of PTO.

Some long weekends to think about in 2025 are:

• Memorial Day (Monday, May 26)
• Labor Day (Monday, September 1)

Longer Weekends In 2025

Even better than a Friday or Monday Federal Holiday is when one falls in the middle of the week. 

• Veterans Day (Tuesday, November 11) – Taking Monday off extends this into a four-day weekend.
• Thanksgiving (Thursday, November 27) – Taking Friday off gives you a full four-day break. But taking Wednesday or the Monday after gives you a fabulous five-day holiday. 

Using PTO around these long weekends means fewer PTO days used for a longer break, which is key to maximizing precious vacation time.

Strategies To Maximize Vacation Days

Taking time off cleverly lets me get more days away without using too many PTO days. I stretch my time off and enjoy longer breaks by planning around breaks, holidays, and company closures.

By spotting these chances early, I can book vacations or trips during these extended breaks, making my time off feel less rushed and more relaxing.

Combining PTO With Company Closures

If your company closes for specific days or weeks around the holidays, combining planned PTO with those closures maximizes time off. Many companies, including the one I work for, close around holidays or during slow periods, so this is a perfect opportunity to use those days as part of your vacation time.

For example, if the office is closed between Christmas and New Year’s, taking a few PTO days before or after that period equals a more extended break without using many PTO days. Checking your company’s holiday calendar as soon as it’s available is key for this plan to work well.  The years when Christmas Day and New Years day fall on weekdays are the best opportunities for an extended vacation using less PTO.

Top Spring Weeks to Take PTO

In spring, taking PTO around mid-February is smart. Using a few PTO days around Presidents’ Day can give you a nine-day stretch off work by combining weekends and holidays. Another bonus of planning a vacation in February is lower-priced vacations, as it’s off-season for most travelers. 

Best Fall And Winter Options

Fall offers solid PTO opportunities near Columbus Day, Veterans Day, and Thanksgiving. For example, Columbus Day is always the second Monday of October. Plan to take PTO on the Friday or Tuesday following Columbus Day to get a four-day weekend. This year, I am taking my son to Dublin for that long weekend. We will leave Thursday after school and be home late Monday. 

Winter offers excellent value at year-end. Thanks to the Christmas and New Year’s holidays, taking just five PTO days after Christmas can create an 11-day break. This is perfect for those wanting a nice long vacation without using too much PTO.

Quick tip: Plan early, since these are popular times. Using fewer PTO days around federal holidays really stretches your time off.

Sample PTO Calendars For 2025

Knowing when to take PTO can help stretch your time off by using holidays and weekends. Planning around key dates and mixing shorter PTO periods with long weekends gives you more days away without using all your leave.

Here’s what you PTO calendar could look like for 2025:

• February: Take off 4 days (Feb 18-21). You get 9 days off from Feb 15 to Feb 23.
• May: Use 1 PTO day on May 23, add Memorial Day weekend for a 4-day break.
• June: Take June 20 (Friday) and June 23 (Monday) off for a 5-day vacation.
• Late August: Taking August 29 off can create a 4-day weekend for Labor Day.
• Late December: Taking 5 days of PTO (December 26, 29, 30, 31, and January 2) off will get you a 11-day vacation.

Other Tips for Maximizing Use of PTO

When traveling, I try to fly overnight or early morning. It makes the most of my first and last day. Combining smart travel with my PTO means I can maximize relaxation without cutting into work too much.

Using these tips, I turn my precious few days of PTO days into weeks of rest or adventure.

Start Planning for Spring 2026

Planning early is key to maximizing my time off and value for money. I am not certain of the school calendar for next year, so I haven’t booked anything, but I know from experience that the calendar will be sent out before the end of May.

I am writing this article in April 2025 and am already planning vacations for Easter Weekend 2026. Easter weekend dates are in every calendar, and I know that on Good Friday, both kids will be out of school, and my Husband and I will not have work.  I assume they will have a Teacher In-service holiday on the Monday after Easter because that’s been the trend.  For 1 day of PTO, the family gets a four-day weekend.  We will leave town after school on Thursday and probably enjoy a late-season ski trip.

Final Thoughts About Maximizing PTO in 2025

Start planning your 2025 and beyond by getting organized.  I suggest using a calendar format that shows the full year.  Mark off the Federal Holidays when work/school will be closed.  Add other important dates/events.  Just with this information you can start to see weeks where adding a day or 2 of PTO can give you enough time off for a real vacation.  By planning this way, I can turn a few PTO days into multiple days off for rest or short trips. Trust me, it feels good to make my time off work smarter, not harder.