Work Less, Travel More: Strategic Planning for How to Maximize Vacation Days in 2025

When I first started working full time, at my “big girl job” as I like to call it, I was allotted 21 days of paid time off (PTO) per year, but the catch was that included all the holidays.

In reality, the time ended up being around 2 weeks, depending on where the holidays fell on the calendar. I also had stringent restrictions on when I could use these days. That meant that the week between Christmas and New Year’s Day was off-limits, for example.

I’m sure many of you would agree that the thought of requesting time off can be intimidating—I worried about the mountain of work that would greet me when I returned and whether taking a break might reflect poorly on my work ethic.

Yet, despite these fears, my love for travel and exploring new places only grew. Over the years, I’ve mastered the art of stretching my limited vacation days to enjoy multiple long weekend getaways, turning brief windows into the ability to adventure all year long.

I’m excited to share the strategies that have allowed me to transform holidays and single PTO days into extended vacations. While these aren’t always the cheapest days to travel, we’ve found ways around taking big hits to our budget by being flexible about the destination and spending the night in our tent!

Whether you want to explore a new exotic destination, spend some quiet time outdoors, or unwind on a beach somewhere, these tips will help you navigate the 2025 holiday calendar to maximize your well-deserved time off—proving that even with limited days, you can still have more than one great out of office adventure per year.

Let Go of Vacation Guilt.

Feeling guilty about taking time off? You’re not alone. In my first year of full-time employment, I only used 3 of my allotted vacation days. Now, when I think about that, I’m embarrassed.

The ones that went unused didn’t roll over. I didn’t get a payout or anything for not using them. I just felt guilty for not being at work. Now, I feel guilty that I didn’t take advantage of the benefit. I just lost them.

Here’s how to shake off that guilt and make the most of your vacation days:

Plan Ahead: Tackle tasks in advance. The more you prepare, the less you’ll worry about work while away. Worrying about work is a surefire way to have a bad vacation!
Delegate: Trust the other members of your team by handing off some responsibilities while you’re gone. Prepare them before you go. It’s good for you and empowers them.
Set Boundaries: Make it clear when you’re off the grid. Good communication helps set expectations with your team. Your work will be there when you get back.

Remember, vacation days are part of your compensation. They’re not a favor from your employer. Taking that time off can help you be more productive and feel better mentally when you return, among other benefits. Use it!

Understanding Your PTO: When Does It Reset?

Knowing when your PTO resets is key for optimal planning. Most companies reset PTO annually, starting on January 1st.

However, you’ll want to confirm the specifics with your HR department. This will help you schedule vacations without losing any hard-earned days, like I did.

Strategic Planning for the Year

Plan your vacation days around holidays and long weekends to extend your time off. Here’s how:

Utilize Public Holidays: If you get public holidays, plan to add a day before or after them to create longer breaks.
Divide Your Vacation Time: Spread your days across the year to prevent burnout and keep things fresh. If you only get 1 week of PTO, taking a few long weekends throughout the year can be more beneficial than only one weeklong vacation per year.
Consider Partial Days: Break down your PTO into hours for half-days if possible. You can use that time to reach your getaway destinations earlier, extend weekends, or take a personal afternoon.

A serene sunset at Pacific Beach in San Diego with a long pier extending into the water. The sky is a gradient of warm orange and yellow hues, fading into the deep blue of the evening sky. Silhouettes of people are visible on the beach, adding a peaceful and tranquil vibe to the scene. — Using 2 days of PTO, we spent a 5 day-long weekend enjoying these beautiful San Diego sunsets.

Take Advantage of Long Weekends.

Long weekends are golden opportunities for mini-vacations. This is one of our favorite ways to travel, and we plan multiple long weekend trips each year.

Here’s how:

Extend Your Weekend: Add a day off to a Monday holiday for a four-day stretch.
Piggyback on Business Trips: Extend work trips by a day or two to explore new cities.
Look for Midweek Holidays: Thanksgiving is always on Thursday, so plan Friday off, too. Check where variable holidays like July 4th and Veteran’s Day fall during the week.

Plan a Full Week Off- Strategically.

Taking a full week off lets you unplug and unwind from daily stresses entirely if you have PTO available.

👉🏼 Pro Tip: Select your week during a quieter time at work to minimize stress for you and your team.

Consider taking a week off around another holiday, such as Memorial Day, July 4th, or Labor Day, so you only have to use four PTO days instead of five.

A peaceful scene of a lush green lake surrounded by dense forest in the Azores. A person sits on a fallen tree trunk by the water's edge, enjoying the tranquil view. The calm green water reflects the foliage. — When July 4th fell midweek, we leveraged it to explore the island of Sao Miguel, in the Azores, for longer

Do you have Floating Holidays?

Check if your company offers floating holidays for more flexible scheduling.

Maybe you can float that Wednesday holiday to Tuesday or Thursday, and create a 4-day weekend with only 1 day of PTO.

Not all companies have this benefit, so if yours does, consider yourself lucky. Also, if you have this option, just be sure to provide plenty of notice and discuss it with your manager to make arrangements ahead of time.

Work When Others Aren’t.

One of the most strategic approaches to maximizing your vacation time is to work when the majority of your colleagues are away. This tactic is especially useful during the common vacation periods, such as the week between Christmas and New Year’s.

Here’s why and how you can benefit from this approach:

Less Workplace Distraction: With fewer colleagues around, the work day tends to be quieter and less hectic. This environment can increase your productivity!
Efficient Use of Vacation Days: By choosing to work during popular vacation times, you can save your PTO for less popular times of the year. This not only helps you face fewer crowds, meaning you can cover more ground during your time off. You can also find better deals during off-season or shoulder-season travel!
Potential for Flex Hours or Remote Work: Depending on your workplace culture, being one of the few in the office during slow periods might also give you leverage to request more flexible working hours or the opportunity to work remotely.

Consider Asking for Unpaid Time Off

Taking unpaid time off is a valuable option for extending your vacation beyond your paid leave entitlements.

Only do this if you’ve carefully planned and budgeted ahead of time!

Here’s how I’d approach this:

Communicate Early: Requesting unpaid leave well in advance respects your employer’s need to plan and increases the likelihood of approval. This foresight helps maintain flow and minimizes disruption.
Discuss the Benefits: Highlight how taking this time off will allow you to recharge, ultimately boosting your productivity and creativity when you return. Emphasize the personal benefits, such as attending to family matters or pursuing personal interests, which increase overall job satisfaction and performance.
Be Mindful of Your Team: Prepare for your absence by delegating tasks, and make sure your responsibilities are covered. Clear communication with your team and manager is key!

This way, you can enhance your work-life balance without impacting your financial stability or your team negatively. Both you and your employer can benefit from such arrangements when handled thoughtfully.

A snowy forest scene viewed from a ski lift, with snow-covered trees lining a ski trail. Two sets of skis dangle in the foreground, suggesting the perspective of skiers heading up the mountain. — Use those holidays at the beginning of the year to enjoy a winter adventure!

How to Maximize your Paid Vacation in 2025 (2025 Holidays)

Planning your vacation around the 2024 holiday calendar can help you maximize your time off. Here’s a guide to making the most of the major holidays:

Martin Luther King Day (January 20, 2025): Leverage this long weekend by taking the Friday before or the following Tuesday off, turning a three-day weekend into a four-day break. This is an excellent opportunity for a winter getaway or a staycation.
President’s Day (February 17, 2025): This holiday often sees fewer people taking extra days off. Consider taking the same approach as we did with MLK Day in January, and use a day or two before or after to visit destinations when they’re less crowded or enjoy winter sports.
Memorial Day (May 26, 2025): Kick off summer with a bang by planning a nine-day vacation. Taking four days off around Memorial Day allows you to enjoy extended travel, like hiking in a new National Park, relaxing on the beach, or taking a longer flight.
Europe or Central America, anyone?
Juneteenth (June 19, 2025): Use this day to engage in local celebrations or plan a short trip around cultural exploration. It’s on a Thursday this year, so can also leverage it into a four day weekend by also taking Friday off.
Independence Day (July 4, 2025): Since the holiday falls on a Friday, consider taking a couple extra weekdays off to extend your celebrations or enjoy another summer trip. This is a perfect time for family gatherings, fireworks, and summer national park visits.
Labor Day (September 1, 2025): The unofficial end of summer is a great chance to take one last summer camping trip. Extend this weekend to relax before a busy fall or explore new destinations before winter weather hits.
Indigenous Peoples’ Day (October 13, 2025): Use the long weekend for a quick autumn leaf-peeping escape, since this is a Monday holiday. It’s usually around prime time here in the Northeast!
Veterans Day (November 11, 2025): A day to honor our service members, this can also be a quiet time for a short, local trip or to prepare for the upcoming holiday season. It’s on a Tuesday this year, so take Monday, too, for a four day weekend.
Thanksgiving (November 28, 2024): Many people take the day after Thanksgiving off. Consider doing the same to have a four-day weekend, perfect for visiting family or hosting friends. Sometimes, we even use this long weekend to travel to a college football game.
Christmas – New Year’s: The festive season is ideal for taking extended time off as many workplaces operate on minimal staff. This might not be an option for everyone, but take advantage if you can. Plan to use your remaining PTO, if you have any, for a relaxing end to the year, or start the New Year refreshed.

By strategically using your time off around these dates, you can significantly increase your leisure time without using so much PTO. We want you to get the most out of your vacation days in 2025!