Get Your Holiday Time Off Approved for Thanksgiving, Christmas and New Year’s

Got your end-of-year holiday time off approved yet? With the end of 2019 in sight (for some the trigger is while you are on a much needed summer vacation break; for others it could be when people start talking about Halloween), it’s time to sort out when to take your remaining vacation days. This is the time to map out ways to leverage your official holidays for vacations during the Thanksgiving, Christmas, and New Year’s break. Plus you don’t want to lose unused vacation days before the year is up!

So get out your calendar and start tracking your paid time off usage (try the VacationCounts web app to help). Company holidays are just as valuable as vacation days, but in many jobs everyone can’t be out of the office at the same time. So get your holiday time off approved before it’s too late.

Holidays End of 2019 - Thanksgiving, Christmas, New Years

Bonus Tip: The Black Friday shopping sale is a great opportunity to save big money on your next vacation. Search for travel deals happening on Black Friday and Cyber Monday to book a trip during the Christmas holiday or look ahead to 2020.

How to Take Your End of 2019 Vacation Days

You will need to consider the total number of vacation hours remaining according to your most recent paycheck stub, the roll-over policy at your employer, and the list of holidays recognized at work. The last two months of the year include a handful of company holidays and with it the opportunity to turn one or two “free” holidays into a full week or two of vacation.  I’ve compiled a list of all the possible holidays left for the year which may appear on your official List of Holidays, along with advice on how to leverage the holidays to maximize your time off from work.

You may have read the blog post about Traveling to Europe for Thanksgiving as opposed to staying in the USA for traditional holiday family celebrations.  Regardless of whether you take time off for family, travel, or enrichment during the Thanksgiving, Christmas and New Year’s holidays, now is when you must put your plans in motion. Are all your vacations days and PTO accounted for?

Checklist: Turn 2019 Holidays into Vacation Opportunties

Take Off Holiday Calendar Checkmarks

To make the most of your company closures as the end of the year approaches, follow this step-by-step guide to take more holiday time off. Since taking off a week of vacation during the Thanksgiving, Christmas, and New Year’s holiday periods are very popular, you’ll want to act before it’s too late.

  1. Check your most recent paycheck stub or login to the HR employee benefits portal to view and calculate the exact number of vacation days you have left to use in 2019.
  2. Double check your HR employee handbook to determine how many days (if any) you can rollover into 2020 in case you decide to extend your New Year’s holiday into January.
  3. Consult your list of official company holidays to see if you have one or two days each for Thanksgiving, Christmas and New Year’s or if you are in a role that requires that you work the holidays and can take that time off in lieu.
  4. Review the time off request system at work whether it is a vacation portal, shared company calendar, or paper forms to verify limitations on when you can take vacation days at the end of the year.  For example your company may have a whoever asks first or seniority policy regarding vacation day requests so that everyone does not take off from work at the same time.
  5. Read the rest of this travel hack article to decide how many vacation days you wish to use to pad your Thanksgiving, Christmas or New Year’s holiday weeks to get a long weekend or full week off from work.
  6. Put in your vacation requests as soon as possible to get them approved and on the calendar.
  7. Once approved start planning for whatever it is that will help you live life to the fullest during the festive holiday season. For me that is more travel, so booking flights and hotels early is key to saving money and getting the desired vacation experience.
Paycheck Stub Sample with Vacation Hours

Consult this government website for the U.S. federal list of holidays for 2019 or a more comprehensive list of Holidays and Observances in the United States at the Time and Date site.

Thanksgiving, Christmas, and New Year’s Official Holidays for 2019

Thanksgiving Day – Thursday, November 28, 2019

Thanksgiving Day comes on the 29th of November this year. Employees in America can be glad that most companies offer a full day off as most businesses and government offices are closed. Of course those in retail (online and brick and mortar) are preparing for the after Thanksgiving holiday sales and it may be a stressful time leading up to the Thanksgiving holiday both at work and at home.

My advice on traveling by trains, planes, and automobiles that day (movie pun intended) varies based on where you live and the likelihood of stormy weather or traffic delays. Search online for advice for your home town and final destination and mode of transport. Regardless of whether you are traveling for family or vacation, hopefully it represents the beginning of an unforgettable period of time off from work.

Day After Thanksgiving – Friday, November 29, 2019

While the Friday after may be a paid holiday at your place of business, it is definitely not as widespread as it should be in my opinion.  While many employers offer the day after Thanksgiving off, those working in retail and shopping and related services will find themselves as busy at work as ever.

Even if you do not have the day after Thanksgiving as an official company holiday, Americans should consider allocating one of their PTO days to turn the official “day of thanks” holiday into a four-day weekend.  The kick-off to the Christmas and holiday shopping is both a fun and stressful time for many, so why not head out of town on a much deserved vacation?

For those of you who are fortunate to get this day off, consider the perspective of people who are forced to work.  Give them a bit of slack, be patient and (at least in your mind) thank them for making your day off enjoyable while they have to work hard on Black Friday.

Christmas Eve – Tuesday, December 24, 2019

This year Christmas Eve arrives on a Tuesday with Christmas Day of course happening on Wednesday.  Like the day after Thanksgiving, too many employers do not offer this as a paid holiday.  Since productivity goes way down on the day before the actual Christmas holiday, a paid day off would be smart HR policy.

The best way to extend your Christmas holiday time by taking as few earned vacation days is to ask for Monday the 23rd plus the 24th if necessary.  Hopefully you already have Christmas Day as a paid holiday like most of the working population.

Christmas Holiday - December 24 and 25, 2010 - Calendar Entry

Christmas Day – Wednesday, December 25, 2019

It is safe to assume that almost all full-time employees receive Christmas Day off with minimal exceptions for public health and safety.  As with all jobs there are those of you who have to work on a holiday due to the nature of your role in society and we are all be grateful for your service.  At least a minimum staffing level must be sustained in jobs such as police, fire, hospital staff, essential services and those in transportation (like the people running the airport).

For employees who receive both Christmas Eve and Christmas Day off you will only need 3 remaining vacation days to extend your vacation to an entire week. Ask for Thursday the 26th and Friday the 27th as paid (or floating or personal or time off in lieu) days off while you can. As for travel during Christmas week you have a bit of flexibility since you could depart of the Saturday or Sunday prior for an extended family visit or a much-deserved winter sun getaway vacation in America.

New Year’s Eve – Tuesday, December 31, 2019

Again we are stuck with a Tuesday for an important holiday that feels more like a Friday.  As with Christmas Eve, many employers do not offer this as a paid holiday and just have New Year’s Day off.  That is a shame since once again not much gets down on the last day of the year, especially after lunch when you and your co-workers are ready to usher in 2020.

Whether or not you plan to stay near home or travel on vacation for New Year’s weekend, request the Monday off in addition so that you can enjoy a fun or relaxing 5 day weekend.

New Year’s Day – Wednesday, January 1, 2020

The final holiday in this list actually falls in 2020 which can be a bit confusing when it comes to annual vacation time off planning.  Most businesses are closed on January 1st and so most employers offer this as your last or first company holiday depending on how you look it at.  Since New Year’s Day falls exactly in the middle of a week, think about extending it in either or both directions to have a longer and more fulfilling break.

The one issue to check on is whether you can roll-over leftover days from 2019 to 2020 to utilize in the new year.  Also it is possible that you may not be able to take paid time off (PTO) in 2020 until you earn them which is impossible if the year just started.  By asking your HR representative the right questions and with a bit of flexibility, you can maximize your time off at the end and at the beginning of the year.

Leverage Company Holidays to Take 1, 2, or 3 Vacations this November and December

Take Off Thanksgiving Christmas New Years Holidays

How many vacation days will it take to turn your Thanksgiving, Christmas or New Year’s paid company holidays into a full week or two weeks of dedicated vacation time?  Do you have enough vacation days including floating holidays, personal days, and PTO left to take the last two weeks of 2019 off entirely? It doesn’t matter as long as you use all of your vacation benefits without losing days you earned by working all year.

I’ve been told that some people prefer to head to the office over the holidays.  The workplace will surely be quiet and you can have more productive time to get things done.  That is a great plan as well, but even better if your employer offers the paid holidays as floating or replacement future days off instead.

For most of us the easy, fun and rewarding option is to maximize your final set of vacation days to fulfill your holiday dreams.  Follow our advice now to plan out your time off to travel during the end of year holidays and be in high spirits when 2019 arrives.