1. Pick Your Dream Destination.
I recommend making a list (or a joint one with your family!) about where to make a priority for the upcoming year. It can be simply a list on your refrigerator or a Pinterest board. (Pinterest can be a great resource for travel/tips inspiration no matter your niche.)
2. Write down all Public Holidays & Total up your vacation days.
However, I definitely recommend tweaking your Facebook settings, so you see budget flight deals by liking Secret Flying then pressing "See First" under the tab where it says "Liked." Sometimes you'll find a steal--and even if you can't use the dates they recommend, you might find inspiration OR an amazing deal on the dates mentioned. I found an amazing deal to Slovenia this way!
If you click "My calendars", create new calendar. Name it whatever you want although makes sure the square with vacation days is colored in. Then, make a new appointment on each of your days off. Remember: WEEKENDS ARE DAYS OFF.
3. Have you ever done a weekend getaway?
Similarly, I like to see how far I can go in five hours by plane, train, or car. Inspiration is the hardest part as it's easy to think I've done X, Y, Z...and there's nothing else to do. My weekend/day trip inspiration is often gathered from a mix of Atlas Obscura (a website that catalogs the weird, wonderful, and historical!), blogs by locals about charming things in the area, pretty Pinterest pins, hiking guides, and local guides to the area. That's how we ended up on the Dutch island paradise of Texel and in the beautiful city of Maastricht in the south of the Netherlands. Although what's close might be so familiar, it's often worth looking into places that you've heard about--but you've put off. It might surprise you.
4. Le Long Weekend
Travel can be exhausting, but if you book flights during your off day OR the day after, you lose out on a full day of vacationing when you could already be there. Sure, it seems a bit stressful, but it will be worth it when you've arrived smoothly at your destination. It's science: Vacations boost your health, including stress levels, for a MONTH after you get back, so 1 hour of stress = lasting benefits.
If you're not going that far, it might be worth looking into flying back the morning that you need to return to work. I know it sounds crazy, but I did a long weekend flying from Amsterdam to the US with taking a half-day off and arriving at 7am before heading to work in the afternoon. This isn't for everyone, but it allowed me to see my family over a long weekend without losing two vacation days to being "in transit" or recovering from jetlag.
6. Do you get to go on work trips OR does a family member travel for work?
As the partner of an academic, I know firsthand that while you're attending a conference, you're usually not sightseeing too much, After a conference that my partner attended in Israel, we visited Jordan. If you can bring your family or partner along (they'll need to pay their way, but you'll save on your own expenses), they might be able to enjoy a free hotel room while sightseeing on their own daytime. You can travel afterwards together, but it's a great excuse to travel!
6. Negotiate your work contract
Note on Flying On Major Holidays
This is especially true if:
A) There is a major public holiday [e.g. New Years Eve] where everyone takes off the same days (e.g. Christmas Day & flies back New Year's Day).
B) You're flying to a remote airport with very limited planes.
C) Very limited accommodation where you're heading.
If you want to book over a MAJOR US holiday, book early and/or shift your dates just a bit to beat the rush. I found an amazing deal over a major US holiday for my parents going from New York to Morrocco. Direct. For $600 Roundtrip. It's way higher now, but booking in advance can work well if you're planning on traveling over a major holiday.