10 Ways to Maximize Vacation Days for Travel

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As a full time accountant who loves to travel, I am always scheming on how I will maximize my time off from work each year.  “As many trips as humanly possible” is basically my motto. If you are a 9-5’er who loves planning trips like I do, chances are you try to stretch your vacation days as well.  Although this is something I am constantly working at, I have developed a few tricks over the years that help me travel more.  In fact, I actually have a spreadsheet that tracks my time off now. I know my PTO balance so well, I’ve even been known to correct our payroll department on occasion. Actually, they are probably sick of me constantly questioning them…

I am lucky enough to have a lump sum of 26 annual vacation days at my disposal.  I know a lot of others don’t get this much, and I certainly don’t take it for granted. Believe me – I’ve worked jobs where my max was 10 days off each year. I am familiar with the struggle of the typical American paid time off limitations. In fact, my husband started off with just 10 vacation days at his company. Yes, I do track his vacation days too. I can be a bit obsessive, but I’d be lying if I said my obsession hasn’t helped us travel to a lot of amazing destinations.

Today I am sharing all the ways I maximize my vacation days to squeeze in 5-6 trips a year while working full time.  I am setting this against the backdrop of my favorite island, St. John, for extra travel motivation!

My Top 10 Proven Methods for Maximizing Vacations Days

#1 – Incorporate holidays into your trip

If you are lucky enough to get holidays off, minimally demanding ones such as Memorial Day, July 4th, and Labor Day are all great options for traveling.  Every year I plan at least one trip over a holiday to save myself on a PTO day or two.  I tend to utilize Memorial Day more than the others, since it’s still early in the season for a lot of destinations, and they usually haven’t gotten too busy yet.  May is also right before a lot of warmer climate destinations become too hot.

We haven’t used July 4th a whole lot, since for some places in the U.S. this timeframe can be a mad house. That being said, last year we traveled to Great Britain over the 4^th of July, which helped us do a ten day trip using only six vacation days!

#2 – Determine if you really need a whole vacation day

This method mostly relates to travel days, or the time you take getting to your destination. Although sometimes taking time off from work can’t be avoided, there are ways around it. For example, shorter road trips may only need a half day or a couple hours off from work. 

For flights, I often try to schedule them for the evening to avoid excess PTO usage.  This means we arrive at night on our first day.  However, I’ve found that when we arrive earlier than that, we spend a lot of time getting settled in and don’t actually end up doing much sight-seeing.  By using the evening for travel and heading straight to bed on arrival, I’m able to start fresh and well-rested for my first full day in a place. I’m fully aware of how exhausting it can be to go straight from work to traveling.  However, if you are trying to squeeze in as many trips as possible, this can be a great way to save some precious vacation days.

#3 – Take a Friday Evening Red Eye

Especially handy for international flights, taking a red eye flight on a Friday evening allows you to do your travel overnight. You’ll likely arrive at your destination Saturday morning (perhaps a bit sleepy), and have plenty of time to settle in.  That way you can work all week and take zero PTO for your travel day.  Even better, you will still have most of Saturday to explore.

The Friday evening red eye entered my life last year when I took my first two trips to Europe.  Icelandair’s short stint in Cleveland introduced this option to me, which I fully embraced for its efficiency.  On our Iceland trip, we arrived early enough the next day to clear customs (and get a new passport stamp <3), pick up our rental car, hit the Blue Lagoon, find our Airbnb, grab dinner, and make an attempt at a Northern Lights tour.  In other words, time management beast mode.

#4 – Look for Good Flight Times

Try to get the best flight times possible to give you the most time efficient trip.  This means arriving to your destination as early as possible to maximize time on your first day, and finding a reasonable flight time home on your last day so you don’t need to worry about going out for a bit on your last night.  Sometimes (but not always) these flights can be a bit pricier.  However, it’s my belief that you’ll remember the extra time on your trip more than the extra money spent, so it’s worth it.

I once again proved to myself this year why it is 100% worth it to pay a little extra for better flight times.  On our recent trip to New Orleans, the cheapest flight home had us leaving Sunday morning at 6:00 a.m..  That’s a lot to ask from someone who just spent the past two days eating and drinking everything in sight in the baking New Orleans sun.  I paid something like an extra $50 or so for flights leaving around 10:00 a.m. instead.  I was so thankful for the extra hours of sleep I had on our last morning, and it was definitely money well spent.

#5 – Try a Quick Weekend Getaway

Whether it’s somewhere easily accessible by a couple hour plane ride, or a reasonable drive from your home, a shorter trip can be just as memorable and relaxing as a longer one.  You’re still leaving town and exploring, but on a smaller scale.  This would let you take just a couple or maybe even no vacation days.

I have become pretty skilled at the quick weekend getaway over time, although many people still tend to look at me like I’m crazy for doing this.  The trick is to drive somewhere within 6 hours or fly somewhere on your side of the country.  Then you’re only talking about a 2 hour flight each way, which gives you plenty of time to explore a new city over a short weekend.  For many U.S. cities, especially eating and drinking focused ones like New Orleans or Las Vegas, a couple days is PLENTY.

#6 – Combine Multiple Destinations into One Trip

Try to see multiple destinations that are near each other in one trip, rather than visiting them on separate trips.  For example, say you would like to visit London and Iceland this year.  If you are flying to London via a layover in Iceland, consider staying in Iceland for a couple days either on your way to or from London.  Not only does this save on travel time, but also saves you on purchasing flights.

We did this last year for our England and Scotland trip.  If you can and have the days for it, it makes sense to just stay on that side of the world and see multiple places in one go.  Sometimes, depending on the location, flying into and out of a country can take one day each way, which could be two vacation days depending on what day and time you choose to leave.  If you do this type of trip more than once in a year, you’re looking at potentially using 4 vacation days just for travel.  Try to save as many days for actual exploring and sight-seeing as you can!

#7 – Negotiate With Your Boss for More Days

This suggestion originated from a commenter, but it’s also something I’ve put into practice this past year. The first scenario of negotiating with your boss for more PTO days involves requesting more days in lieu of a pay raise. I think this is a brilliant suggestion, and something you should absolutely consider.

The second scenario is for those doubting the usefulness of this suggestion due to their company’s policy. Indeed, sometimes you cannot negotiate with your boss for more vacation days because company policy dictates your time off. That being said, I think you should still ask the question. I did exactly this a few months ago, knowing full well that our company policy laid out how many days we get based on years of service. However, just by asking this question, it got my company rethinking how it defined “years of service”. They reframed it, and I ended up qualifying for 5 more days! It just goes to show that it never hurts to ask. The worst they can say is no.

#8 – Convert Holidays into PTO Days

Some companies will allow you to work on a holiday in exchange for a “floating holiday” that you can use whenever you want. It ends up basically being equivalent to having an extra PTO day. I’m not suggesting at all that you start ditching your family gatherings for the sake of more travel. However, if there’s a holiday or two that you don’t mind giving up, it’s worth looking into.

Note that not all companies will allow this. Where I work, I get a floating day during busier times of the year, as I am required to work on certain holidays. In quieter months, I cannot work on a holiday in exchange for a floater just because I want more vacation time.

#9 – Avoid Flying Home Right Before a Work Day

So far I’ve only talked about ways to gain vacation days, but the opposite can also happen. The first involves being smart about when you plan your flight home. If you book your return flight the day before you head back to work, you better hope there aren’t any serious delays or cancellations. I’m a bit of a hypocrite here because I book flights home before work days all the time. However, this finally came back to bite me this year.

I had an unfortunate situation come up in February with a flight being delayed overnight. The original plan was for me to arrive home from our Napa Valley trip on a Monday, and then head right back to work that Tuesday.

Unfortunately, when you travel in winter, there is always a chance of weather delays. This is exactly what happened to my flight, which ended up getting cancelled. I tried to get on several more connections from my layover in Chicago to Cleveland, but everything was ultimately cancelled. By the time I got rebooked on a flight for the next day, my earliest option was in the afternoon. With much bitterness, I had to take an extra PTO day and return to work a day later than planned. As someone who obsessively plans out their vacations days months in advance, I was not a happy camper.

Try to book your return flights a couple days before you head back to work to avoid the risk I’ve mentioned above. If nothing else, you’ll have an extra day to decompress after your trip.

#10 – Stay Healthy

I cannot stress enough the importance of staying healthy throughout the year. This has come to be a very big priority for me this past year, when I started getting more colds than I ever had before. Due to poor self-care, I begrudgingly used 2 of my precious vacation days due to illness this year.

This forced me to take a look at my lifestyle, and reprioritize rest and nutrition. I’ve had to admit to myself that I am no longer in my early twenties, and can’t get away with staying out late on the weekends like I used to. It’s no coincidence that my illnesses always seem to fall after a weekend of partying and hardly getting any sleep. Combine that with periods of stress, and you’ve got the perfect recipe for illness. Bottom line – stay on top of your health and practice self-care on a regular basis to avoid needless PTO days.

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Maximizing your PTO days is not a perfect science, and there will always be a bit of a struggle to balance them. I am constantly learning new ways to use my vacation days efficiently each year. It’s a work in progress, but the above tips have definitely helped me fit in more travel than I thought possible. If you start putting these tips into practice, I promise you’ll see a difference as well!

Which of these suggestions will you use to maximize your vacation days this year?  Or do you have other ways of getting more out of your time off?  Do tell…