One of the situations most employees struggle with is not having enough vacation days to use for a trip, or the company they work for will not allow their employees to take a certain number of consecutive days off. I’m here to help you understand the different ways you can use your vacation days and paid holidays to your advantage and go on a trip that cheats the PTO system.
Unlike most countries, the common 9 to 5 worker in the United States does not have the opportunity to have a month or more off work (sad, I know), but there are ways you can use the given paid holidays to your benefit. Yes, that’s right, you can spend more time on a beach or exploring a city than sitting at your desk! Below I listed the paid holidays you should (conditional on your employer) have off and how you can travel during those holidays in conjunction with your PTO for your benefit. But first, we will review when the most optimal times throughout the year to fly.
If you are looking for a long weekend trip or an extended seven-day trip, I have found that taking a red eye or a night time flight on Wednesday and Thursday gives me the most ideal vacation time. Not to forget, Wednesday is one of the cheapest days of the week to fly! Whether I was flying to California or Copenhagen, taking these later flights allowed me to have extra time on my arrival day to explore, as well as have an extra weekend to enjoy when I was staying in a destination for a week!
Thanksgiving (plus Black Friday)
If you can skip out on family affairs and travel during the holidays, this is one of the best times of year to do it! Not only do most cities start decorating for the holidays around Thanksgiving, but there are many days that are “paid time off” to take advantage of. Most employers offer early dismissal on Thanksgiving Eve, while giving Thanksgiving Day and Friday (aka Black Friday) off. This would equal two and a half-paid days you don’t have to use your personal time for. Leaving earlier in the week or the day of Thanksgiving for a quick weekend trip is not expensive when booked in advance.
Christmas
Christmas is usually spent with family and friends and for most, is probably the busiest time of year for all social plans. For many companies, it is when business starts to slow down as Q4 is ending. I believe this is the perfect time to go on that much needed vacation for some R&R, whether you were able to convince your family to join you, or if that vacation time was intended to be a solo trip this time around. Depending on what day Christmas falls on, you can extend your vacation or use your observance day to your benefit. This can also include Christmas Eve if your company allowed you the paid (of half day.)
For example, this year Christmas happens to fall on a Monday (yikes), but if you plan on traveling this works in your favor. Since you have Monday off, you can go on a five to six day vacation by only taking two to three days PTO. Subject to your destination it would be best to take an overnight, red-eye, or early morning flight to maximize the time you have. This gives you a full day from the date of your arrival until the day of your departure home. Which means at least five full days of sipping drinks at the swim up bar or hitting the slopes. The only downside to traveling during this time is that flight prices can be expensive, but if you decide to fly home on Christmas Day, it will decrease the cost.
Although you will have more time for activities, coming back home the day after Christmas may cost you a pretty penny. If you want to spend your holidays away from home and with or without your family, this can be the perfect gift while using the rest of your PTO before it expires at the end of the year!
New Year’s Day
Much like Christmas, New Year’s works the same way when relating to the amount of time you get off, except you won’t have the guilt of not spending this time with your family. What a way to ring in the new year while celebrating it on a vacation! This is the most ideal holiday to spend a trip on as all companies are closed. Hopefully, the year you decide to travel during NYE will fall close to a weekend, meaning you can extend your vacation or use your observance day to your benefit, just like Christmas. The reason why it is more ideal to travel during New Year’s rather than Christmas is because you miss the holiday travel of Christmas.
Christmas + New Years
Since Christmas and New Year’s Day are a week apart, you can use the combination of: paid days off from both holidays to your benefit and go on one long holiday. Some companies even give the entire week from Christmas New Year’s off for their employees to have some sufficient time to rest and recharge! The trick to saving money while traveling during the busy holiday time would be to leave on the days that people would not be flying to visit family. This would be a few days before (21st or 22nd) Christmas or leaving the day of Christmas. Your return flight would have to be scheduled on the 2nd or 3rd of January. This can potentially give you four days of PTO that you can use with your vacation days. Luckily, January 2nd and 3rd fall on a Tuesday and Wednesday which are the cheapest days to fly during the week. In total you can be spending a two-week vacation while only using five to seven vacation days.
Martin Luther King JR Day, President’s Day, Juneteenth, Columbus/Indigenous People’s Day
These are a couple of popular holidays for employers to observe during the year that are great to use to your advantage and take a trip. If your birthday happens to fall in a month where one of these holidays is celebrated and you get the day off, try to take your birthday day (if given) during that weekend and book an extended vacation! Every February I use President’s Day to plan a vacation around as it is also my birthday month. During the winter season, it is a lot simpler to travel to European cities. Flights are fairly cheap, and tourism isn’t as prevalent as traveling in spring through fall. This is also a great time to take a quick weekend trip to a neighboring city.
Memorial Day
There isn’t a better way to kick off summer than vacationing during Memorial Day weekend. It is the beginning of tourist season (so the crowds aren’t too crazy), you have a paid day off, summer Fridays start, and the weather is absolutely beautiful! Make it a long weekend trip.
Independence Day (4th of July)
This is one of the most expensive holidays to travel (within the U.S.) if you decide to leave two to three days before or after Independence Day. However, if you are traveling during the holiday, you can use it to your advantage. For about four years in a row, my family and I celebrated (or rather skipped the celebration) and were lounging on the sandy beaches of Greece, without a red, white, and blue firework in sight! Contingent on your company’s policy, you could potentially have two paid vacation days to celebrate the Fourth of July. If you want to spend a week sipping Pina Coladas on the beaches of Miami or stuffing your face with pizza in Italy, you could use the long weekend advantage and potentially take three PTO days instead of five.
This past 4th of July I spent the long weekend in Arizona for a bachelorette party. I only had to take one PTO day for the five day trip (Friday-Tuesday) as my employer gave us Monday and Tuesday off to celebrate the holiday.
Labor Day
As the summer winds down, everyone is taking their final trips or relaxing at home, enjoying the last days of summer. Considering everyone is still in summer mode, this is one of the best ways to beat some of the crowds while using your summer Fridays and the paid holiday (Labor Day). You can take a long weekend trip by booking a flight right after your summer Friday hour ends (or if you get the day off the night before), which will give you more time to explore when you reach your destination, possibly saving you a full day! If you decide to take a week vacation, you can use Labor Day to fly home as it is on a Monday and less expensive to fly than a Sunday. Most children and college students would have started school already, which is beneficial for those travelers who are childless or prefer to be at a destination where there are less crowds with children!
Employee Birthday
If your employer gives you a day off for your birthday and you are allowed to use it any of your birthday month this is a huge plus, especially if your birth month already has a paid day off. If allowed, take your Birthday day on a Monday or Friday where you can take a long weekend vacation somewhere to celebrate.
Summer Fridays
Contingent to your employer, make sure to use your Summer Fridays to your advantage for a vacation. My employer lets us have the day off, so during my two week vacation to Greece, I only had to take eight days of PTO instead of ten! If your Summer Fridays consist of getting out at an earlier time, you can use this to your advantage and book an afternoon/nighttime flight which will give you a whole day on your trip!
Working From Home/Remote
If your employer allows you to work from home/remotely and you are planning a trip, it is best to fly the day before your trip or make sure you land early the day of the start of the trip. Traveling takes up a lot of your vacation time and strategically planning your travel time in your favor can give you more time for R&R and less time trying to get to your destination. Working from home or remotely allows you to already be working in your destination!
Whether you want to spend a few weeks away from home or take a quick weekend trip, there are many ways to use the paid holidays to your advantage that correspond with your PTO days to minimize the actual number of days you need to take off. Of course, budget is always top of mind when traveling, but if you can be flexible with your destination, accommodation, and travel, you can use all these days to your advantage and go on three to four trips a year! As always, make sure to use all your PTO and never let them go to waste. I know I am sick of looking at my screensaver of the destination(s) I’ve always wanted to go too, (and I’m sure you are too!) So, let’s make it happen and beat the 9-5 paid holiday system!
