Travel Tips

Easy, practical ways to maximize vacation days & bliss out

Maximize days off to take a dip in the water

Is it just me or can strategizing to maximize vacation days feel like a covert mission? Scouring the calendar, researching what to see/do, and stalking flight prices. It can be a lot of work!

You may not know this, but the US doesn’t have a legal minimum of paid time off (PTO); if you get it, it’s because your employer provides the time. So, like most Americans, I have limited paid time off – 15 vacation days per year, to be exact. With this, I use every trick I know to maximize my vacation time.

I know the pains of strategizing to get the most out of every trip and feeling like I’m never going to make it to all the places I want to go simply due to the limited time I have every year.

I’ve figured out ways to maximize my vacation time and want to help you do the same. Below I’ve outlined some easy, mostly practical, ways of getting the most time off you can every year.

Plan trips efficiently to maximize vacation days

It’s easy! There are three main ways I recommend maximizing the number of days you have for a vacation.

Plan travel over weekends

The first, plan your travel over weekends to get the most days for every trip. I use this trick to get an extra 3-4 days for every trip. The downside is that airports tend to be more crowded/flights more expensive for weekend travel. For me, I think it’s worth the little extra to maximize my vacation time and squeeze in as much time as I can in my destination

Acorn St, a most instagrammable Boston spot
Acorn St, Beacon Hill, Boston

Weekends are especially great for short getaways or road trips to different places, like Boston, for instance.

Book flights for the night before your first day off

I also recommend booking flights the night before your first day off. Every trip I take, I try to leave after work the night before. For instance, I fly to Europe fairly frequently and if I take a flight leaving at 8:00 p.m. I don’t have to use a vacation day for travel.

Doing this for Europe is great because due to the time difference I arrive in the morning and get to enjoy the whole day. This doesn’t work as well for all destinations, but still worth doing.

Return on Sunday

Maximize vacation days and enjoy the view in Manuel Antonio, Costa Rica
View from Hostel Visa Serena in Manuel Antonio, Costa Rica

I also tend to return from my vacations on Sundays. This is far from my favorite way to maximize my vacation time since I know getting up for work Monday morning will be a struggle, but I still find it worth doing. By returning on Sunday I get another day to explore (and eat) and enjoy my destination before returning home.

I do this often, including for a trip to Costa Rica in 2019.  Monday is more or less difficult depending on the time difference between where you’re coming from and your home.

Work on holidays to earn more vacation days

Depending on what you do, your company may require that someone from your team work on holidays. For what I do, my company requires this and I work every holiday I can.

Northern Lights with Greenlander Tromso, Norway
Photo courtesy of Greenlander tours, Tromso, Norway

Working several holidays gave me the extra days I needed to take a 10 day trip to Luxembourg, chase the northern lights in Norway, and roll-over a few days to the next year.

In exchange for working a holiday I get a floating day off; a day I can take whenever I want. I don’t live close to family and we’re not huge on celebrating holidays anyway, meaning this works really well for me. This is probably my favorite way to maximize vacation days.

Use personal days

Using personal days to maximize vacation time is one of my personal favorites. This again depends on your employer; if your personal days are lumped in with sick days, you might not want to use them for vacation.

In my case, I get two personal days that I use for vacation. Using these brings my annual total of paid days off to 17, which is pretty decent for where I am.

Travel over holidays to maximize time off

I know, this one seems pretty obvious and it’s one most people can probably do. I know it can be difficult to get away during the major holidays (looking at you, Christmas & Thanksgiving), but there are other holidays that can be easy to get time off around.

Maximize days off to take a dip in the water
Swimming hole in Cayman Brac

Every year I try to travel over holidays, usually either Martin Luther King Day or President’s Day. These holidays are in the middle of winter and people don’t typically have large festivities to attend and give me an extra day to maximize my vacation days.

In the winter, I’m a big fan running away from Boston to somewhere warm.  The Cayman Islands are a particular favorite destination during this time of year.

Depending on what U.S. holiday schedule you go by, (stock exchange holidays vs. federal holidays) you get 3 or 5 Monday’s off every year. Use these weekends; if you travel over holidays enough, you can save your days off and maximize your vacation time for another trip!

Get an extra day off by donating to charity

This one totally depends on the company you work for. After working holidays, this is my next favorite way to maximize vacation days. Why is it a favorite if it costs me money? Two reasons: it feels good to give and in exchange I get a day off that can be used whenever I want.

How does this work? Again, it depends on your work. I love the company I work for; it’s a great company overall, especially in the world of finance. At the beginning of the year (maybe the end?) I can elect to donate a percentage of my yearly pay to the United Way.

My company is partnered with the United Way and the total contribution I give is deducted from each paycheck throughout the year, which makes it easy for me to manage.

Check with your employers HR if you want to know if they offer this. If they don’t, maybe you can suggest it!

How to use work-from-home to maximize vacation days

Having the ability to work from home is huge! I’m thankful I have this option; it can make life so much easier.

Utilizing work from home to pad vacation time is simple. If you have a flight close to the end of your workday, work from home that day (or just the afternoon) if your home is closer to the airport than work.

Take your computer to the airport with you. This is a great option if your flight is really close to the end of your workday. Most airports have free WiFi these days and connecting is simple; just login and work while you wait for your flight to start boarding.

If you know you’re going to have a day or half a day at your location where you have nothing to do, work! I’ve taken trips where I’m meeting friends at their homes and they might still be working. Rather than waste a day I work from their house to maximize paid time off.

Tips to maximize vacation days for longer trips

Planning for longer trips can be challenging, but if you want to go somewhere that involves a longer than average flight, extra time is definitely preferable.

When I took a 10 day trip to Norway over the summer I was working for a company that provided 12 annual vacation days a year. That year it was really important that I did everything I could to maximize my vacation days.

When I know I want to go to a location that is more challenging to get to (18+ hour flight), I plan far in advance. Like, a year in advance. Since I know I’m going to want at least 2 weeks (10 days, minimum) for a trip like this, I try to do two key things.

Lofoten, Norway

First, I plan the trip over a holiday, which is the easier part. The second action I take is to absolutely maximize vacation days for the current year. I don’t want to use all of my vacation days on one trip and to avoid this I like to roll-over some days from the current year (say, 2020) to the year of my longer vacation (2021).

What are roll-over days? These are unused vacation days from one year that can be used the following year. I don’t always have extra vacation days at the end of year, but if I employ a lot of ideas provided in this post, I can manage it.

How to use work-from-home to maximize vacation days

Having the ability to work from home is huge! I’m thankful I have this option; it can make life so much easier.

Utilizing work from home to pad vacation time is simple. If you have a flight close to the end of your workday, work from home that day (or just the afternoon) if your home is closer to the airport than work.

Take your computer to the airport with you. This is a great option if your flight is really close to the end of your workday. Most airports have free WiFi these days and connecting is simple; just login and work while you wait for your flight to start boarding.

If you know you’re going to have a day or half a day at your location where you have nothing to do, work! I’ve taken trips where I’m meeting friends at their homes and they might still be working. Rather than waste a day I work from their house to maximize paid time off.

Work longer hours the days prior to leaving to maximize paid time off

When I have a flight in the afternoon, before the end of my workday, I like to make up the hours I need to take off on my day of travel earlier in the week.

For instance, if I have a flight that’s at 4:00pm and don’t want to work from the airport, I’ll work extra time the days before departure. I’ll work enough time to get to 40-hours and avoid using 2 or 3 hours of vacation time on my day of travel.

Convert overtime: work more, get more

Some employers (not mine) give the option of converting over time worked into vacation time. The idea is that instead of getting paid more for the worked outside of the 40-hour work week you earn an hour of time off.

Maybe you’d rather have the extra money, or maybe you’d rather use this to maximize vacation time and squeeze in another trip or two.

Not sure if your company offers this option? Reach out to HR to find out.

Buy a vacation day or take a day without pay

When it comes to maximizing vacation time, neither of these options would be my first recommendation. Not getting paid isn’t fun and for a lot of people this wouldn’t be an option. Whether or not this is an option for you, again, depends on your employer’s policy.

This actually isn’t an option for me; it’s not offered by my company. However, if this was an option for me, I would use it sparingly. For instance, if I had 4 vacation days left I would take an unpaid day to get to the weekend and a couple more days.

Move to Europe

Not the easiest or most practical of options but would be my number one choice. Europe, in general, is much more generous with vacation time than other parts of the world. If you’re in a position to move there, go for it!

Maximize vacation days and go to Luxembourg!
Adolphe bridge, Luxembourg

Personally, I’m strategizing to make the move back, hopefully to Luxembourg, where, for example, most financial institutions are part of an agreement that provides 36 days of vacation year – not including holidays!

Need help planning a trip?

Let me know! I LOVE planning trips!

Get my FREE Travel Organizer!

Let's be friends and I'll send my FREE Travel Organizer directly to your inbox!

Were these tips helpful? Pin them for later!

«

2 COMMENTS

  • Rachel-Jean Firchau

    this article is filled with great tips! thanks for sharing!

    • thisunsettledlife
      AUTHOR

      Thanks, Rachel! It’s important to get the most and best vacations in every year 😀

Leave a Comment

Your email address will not be published.