A Beginner’s Guide to Maximizing PTO in 2025

If you put a little strategy behind it, you can really maximize your Paid Time Off (PTO) in 2025. By hacking my PTO, I was able to take 11 trips in one year… all while keeping my full time job. This blog will help anyone trying to make the most out of their PTO in 2025 and give all of the 2025 PTO hacks in one place.

Going into next year, NOW is the time to start planning your PTO. Here’s why:

It’s the perfect time to get a deal.
You can not only maximize your PTO, but you can steal it off of the calendar early without getting beat out by teammates.
You’ll have enough time to plan without stressing.

Let’s dive into each one. If you want to cut to the chase, click into HOW to Realistically Maximize Your PTO here.

Why Now Is the Best Time to Plan 2025 Vacations

Reason 1: Travel Tuesday is Around the Corner

Travel Tuesday is the Black Friday of travel. It’s the Tuesday after Thanksgiving– December 3, 2024 this year. This is the perfect day to get the best deals on flights and hotels. Keep in mind, these are some of the biggest expenses of the trip. I’ve been able to book some 4 star hotels for half off because of these deals.

If you start planning out your travels now, meaning a few weeks before Travel Tuesday every year, you’ll know exactly what to book when you get there. I recommend having which days you’re going to travel on (when you’re going to take PTO), and what destinations picked out before that day. I’ll explain the whole process below here.

Reason 2: Maximize Your PTO and Actually Get It Off

If you plan out your PTO before the year even starts, you have 2 benefits:

You can plan it out all at once to strategically use it (and actually book a ton of trips)
You can book it before the rest of your team to actually get it off

By booking your PTO before the year even starts, and all at once, you can combine it with holidays to make the most out of it. You know when to and not to use it. For example, if you take off the Friday before Memorial day, you’ll be able to get a 5 day trip in by only taking 1 PTO day. All you have to do is fly out Thursday right after work, and come back Tuesday before work. I have a full calendar and guide on how to do it here.

How to Travel with a Full Time Job, Time Hack 1 - PTO calendar 2025

I know you’re thinking it’ll be expensive; but by booking it before the year even starts, you actually get great prices on Holiday travel!

You also have the best chance of getting your PTO approved by your boss if you request it before anyone else. By getting it on the books early, you’ll be first in line for the best days.

Reason 3: You Won’t Have to Stress About Preparing

By starting now, you’ll have a few weeks to actually figure out your travel days and destinations. It’ll give you the time and space to breathe while still working your job. I find that planning slowly over a few weeks gives me the least amount of stress, so I hope it does the same for you!

HOW to Realistically Maximize Your PTO (Short Process List)

Here’s the short of it. It’ll make more sense in the context of an example, which I’ll provide right underneath.

Start by scheduling out your PTO. See how many days you have off, and how exactly you can combine with Holidays in this blog here.
Decide on how many international trips vs domestic trips you’d like to take.
1. This will help weigh which travel dates are more or less important to you. (You’ll likely need to invest more PTO into international travel)
Determine your travel dates based on your calculations above.
Pick destinations based on desire, time, price, and travel dates.
Scope out flights and book them.
Find hotels and book them.
When you get closer to the trip itself, start building out your itinerary!

Real Life Example of Planning 9 Trips in One Year with a Full Time Job

Before I go into a real life example, let me set some ground rules to give context. This example has facets that are based in my life, and some that I’ve changed to relate to others as well. In this example, let’s assume I:

Live in San Francisco
Have 15 days of PTO in the year, in addition to US holidays
Have a few travel credit cards and some points racked up from the previous year
Like to experience new things, engage with the local culture, try new foods, and like adrenaline based activities

With that in mind, this is how I’d go about planning my PTO for 2025:

Step 1: Look into scheduling PTO.

First step is to map out my PTO. I want to figure out how to combine it with holidays. I will use the calendar on this blog. Before I decide on exact dates, I have to decide what types of Trips I’ll take.

Step 2: Look into the types of trips you want to take.

I want to take at least 1 international trip, maybe 2. Otherwise, I’m down for a bunch of domestic trips. That means I’ll probably do 1-2 long trips and a bunch of shorter ones.

Step 3: Actually determine my travel dates.

I often fly out Thursday night, and fly back Tuesday morning (I don’t count that last travel day as part of the trip). With that in mind, I picked these travel dates and why I chose them:

January 17 – 21. (4 day trip, 0 days PTO)
- I’m just starting out the year, I don’t need to take the rest yet.
February 13 – 18. (5 day trip, 1 day PTO)
- It’s Valentine’s day and we want to treat ourselves.
May 22 – 26. (5 day trip, 1 day PTO)
- It’s been a few months, we want to take a break.
July 3 – July 7. (5 day trip, 1 day PTO)
- Some people get more of this off, we don’t, but still want to take advantage of the great weather.
August 28 – September 2. (5 day trip, 1 day PTO)
- Again, great weather timing.

October 9 – 14. (5 day trip, 1 day PTO)
- Why not?
November 6 – 12. (6 day trip, 2 days PTO)
- Veteran’s day is a weird holiday… but why not take advantage of it.
November 21 – December 1. (10 day trip, 3 days PTO)
- Thanksgiving week is a great week to go abroad since they don’t celebrate the same holiday. It could work out for some deals.
December 19 – Jan 2. (14 day trip, 5 days PTO)
- This is the ultimate week everyone takes off. We should too.

Believe it or not, that’s a full 9 trips that you can take in just one calendar year WHILE you’re working a full time job. And that’s not considering anyone who is fully remote or hybrid and can go for longer.

Step 4: Pick my destinations

Based on how long the trip is, I’ll pick a destination that’ll fit the timing. I’ll book places closer to me for the 5 day trips, and places that are farther for the longer ones. I would also look into how much it’ll cost to go to different locations based on this date. Plug the dates into google explore and see what locations come up!

Based on that, here’s what I chose:

January 17 – 21. (4 day trip, 0 days PTO)
- Since this is the shortest, I’ll go close to home. San Diego is only an hour flight and super doable. Plus, it’s one of the places that won’t be too cold!
February 13 – 18. (5 day trip, 1 day PTO)
- We’ll treat ourselves and go to Catalina Island (longer drive or quick flight) to celebrate Valentine’s Day. It’ll give us the vibes of Italy without having to leave California.
May 22 – 26. (5 day trip, 1 day PTO)
- We’ll hit up Vegas to let off steam from the past couple of months at work. Plus, it’s relatively good weather for this time of year.
July 3 – July 7. (5 day trip, 1 day PTO)
- This is one of the most beautiful times to go to Vancouver or Seattle!
August 28 – September 2. (5 day trip, 1 day PTO)
- Napa or Paso Robles since it’s only a 2-3 hour drive and I like wine. Plus, it’ll be nice and warm without getting way too hot.

October 9 – 14. (5 day trip, 1 day PTO)
- I’d spend time on the river in Chicago, or even go to New Orleans.
November 6 – 12. (6 day trip, 2 days PTO)
- Mexico City would be fun to adventure in the dry season! It’ll be perfect weather. I might even take more PTO if I can afford it (if your company gives more time off during this week that’s even better!)
November 21 – December 1. (10 day trip, 3 days PTO)
- Anywhere in Europe is great for this, but I’d land on Morocco since I was able to study abroad in Europe and see a ton of it. Marrakech seems like such a unique place, I’d want to go there or Istanbul!
December 19 – Jan 2. (14 day trip, 5 days PTO)
- This is some of the best times to visit Asia because it’ll be the least humid out of the whole year. I would go to Goa, India or Tokyo, Japan!

Okay, that was a lot. BUT I hope it helped show you exactly what steps to take to realistically get in 9 trips. If you work remotely, you can even get more travel time. But even without it, this is a real life example of someone with limitations that still made it work and then some. While the rest isn’t easy, I personally think this is the hardest part because it’ll decide the main part of your experience.

Step 5: Scope and Book Flights

This process is probably the easiest of them all because there are limited options. For most trips, you’ll be flying on a Thursday night and coming back on a Monday night or Tuesday morning. While this depends on the destination, google flights is the easiest tool to use. Just search your dates and pick the best option based on your budget and timing.

It doesn’t show points though, so you’ll have to either scope out airlines where you have points manually or find an award booker. Regardless, look to fly or drive immediately after or before work to maximize your time. I recommend booking on Travel Tuesday for the best deals.

Step 6: Search and Book Hotels

This is a bit harder because there are almost too many options. I wrote up a full guide on how exactly to find what’s right for you and your trip here, but it’s basically up to your preferences. I recommend doing a search of the neighborhoods in the places you’re visiting to get the vibes and see which one matches you the most, on top of the details of that guide. Once you know where to look, either book with points or use search engines to look for hotels like Expedia, Kayak, and hotels.com. I recommend booking on Travel Tuesday for the best deals.

Step 7: Build Out Your Itinerary

There’s a few ways you can do this. I have some time saving hacks here which can help you build some nice itineraries here for ease. It’ll walk you through the basic process of how to build an itinerary for any trip. The main points are to search by your main interests, book in some staple tourist experiences, and sprinkle in some local ones.

Conclusion

And there you have it! It’s a super long blog I know; but it’ll help you understand exactly what to do step-by-step. Now, you won’t be left wondering what to do. You’ll instead have a process that you can use everywhere going forward!! I hope this was some help to you. If you want to see this in video form where I walk through it, check out my instagram. For other 9-5er tips, feel free to see my list of them here. Happy traveling!!