Working a 9-5 Travel Guide

Travel while working a normal 9-5

At my current job, I have 18 vacation/sick days plus Holidays, and I use every single one of them every year. I end up with about a month of vacation. That’s a lot of travel time if you do it right. Working a steady job doesn’t mean it’s any less difficult to travel than those with a flexible freelance job. It just means you travel differently.


There are certain times of the year (summer for example) that companies are more lenient for people taking trips. Summer tends to be universally the best time for employees to take trips. My company gives us 4 vacation days/summer fridays that can only be used during summer, which encourages us to take trips at that time. When you tack them onto long weekends such as the 4th of July, Labor Day and Memorial Day, you can end up with 5-7 trips that only use 1-3 days of vacation.

Example: I went to Dominican Republic this year for 4th of July. We took an 8 day trip that only used 4 vacation days

If you are going to take off for 2 weeks, it helps to know your industry. For example: For my client, summer is a busy time for selling products, but we plan campaigns in the beginning of the year, so January/Febuary is not a great time for me to take 2 weeks.


Overnight flights are a huge helper when saving vacation days. If you get a 9 pm flight, you don’t miss the departure’s day of work, but be in your destination early the next morning /afternoon. This can give you up to an extra day in places.

For shorter flights, embrace the night flight. Call ahead to your hotel/airbnb/hostel and see if you can have a late check in. This let you start the day in the new place refreshed and ready to go. All the airbnb’s I’ve stayed in have been great about a late check in – Especially if you are coming from far!

Alternatively, embrace the layover. On the way back from Spain, my friends had the option to leave a little later (12 noon) and do a 4 hour layover in Portugal, or leave a little earlier (9 am) and have an 8 hour layover in Portugal. Even leaving later didn’t leave much time for activities. Instead they chose the earlier flight, got to spend an entire day in Portugal, and only got home a little later than originally scheduled. They left their bags checked with the airline so when they reentered, they saved on time through security.

The other great thing about a long layover is that they tend to be much cheaper. Embrace the savings and have an extra adventure!