Vacation Days and the PTO Hustle…

Delta should really clean these scratched up windows, eh?

I started this blog to encourage people who are in situations similar to mine – we have a full time job that we love, but we love to travel just as much. How can we go see as much of the world as we want without risking our jobs and taking off too much time while being within the constraints of our PTO (paid time off)?

I’m fortunate enough to get a good amount of vacation days, combined with comp days, days I earn from working weekends of holidays. Even if you don’t get that much time off, don’t count yourself out. Here are some ways to make sure you can get in that international vacay you’ve been dying to go on.

1. Holidays, holidays, holidays!
I’m a big fan of traveling over the holidays. If you’re okay with a tight trip, you can easily go abroad with just 1-2 days of vacation time, or none at all! Holidays like MLK Day in January or President’s Day in February are great days to plan vacations around. If you book far enough in advance, travel in January and February is cheap in the Northern Hemisphere. If you’re looking to go to places like Brazil or the Caribbean, the prices will be much higher. Memorial Day and Labor Day are my other favorite holidays to travel on, but you definitely need to book early. Travel during Memorial Day weekend tends to be hectic, so make sure you’re up for the challenge!

Of course holidays like Christmas and Thanksgiving will give you more time off, but you’ll need to weigh whether you want to spend the extra money to pay for the higher airfare and if you really want to miss out on your family dinner this year.

2. Long Weekends Abroad
Flights abroad normally leave in the evening – you could take a flight leaving on Friday at 6 or 7pm, leave work a little early and be anywhere in Europe or South America by Saturday morning! I often like to work the morning of my flight and take half a day off to go to the airport for my evening flight. I recently went to Berlin for a long weekend. I left on a Wednesday evening after work and had Thursday, Friday and Saturday to spend in Berlin with my friends, before flying back to NYC on Sunday morning. Was it a quick and crazy trip? Yes. But it was worth it. Leaving on a Wednesday or Thursday is my preference – flights are cheaper on Wednesdays as well. If you hook the long weekend into a holiday, you can have 4 days on the ground before flying back to that wonderful desk job.

Long weekend in Germany

3. Cruising from the Home Port
Okay okay, don’t shoot the messenger. I know a lot of well traveled people are anti-cruises. I see both the pros and cons of cruises. But if you’re looking to get out of town for a few days and want a mindless trip or you really want to take your first international trip and this seems to be the best way – go for it!

If you live in a port town, this can really come in handy. NYC, Baltimore, Boston, Miami, Seattle and LA to name a few, are cities that cruise ships leave regularly from. Forget TSA, forget booking a flight! You can cab it down to the port and be on vacation the very same day. The fact that you won’t have to factor in travel time to and from the ship will eliminate the amount of PTO that you will have to use. Mexico, Bahamas, Aruba, Nova Scotia, the Virgin Islands are just a few of the places that you can see from these ports.

A lot of people hate on cruising because they say it’s for old people or families – which can be true. However, if you choose the time you go wisely, you may not have to deal with either. Avoid the times when school is out of session and may find a bit of diversity on your ship.


If you use any other ways to get more time out of your vacation days, let me know! I know it can be a hassle and the trip can be too quick for most, but I’d rather take the trip now than to keep putting it off until it never happens! Check out the two links below – NY Times has a recurring feature of how to best spend 36 hours in one location – it’s great for a quick turnaround trip. ABC News has an article on how you can use your remaining vacation days, for those that have them.

NYTimes: “36 Hours in…” Index

ABC News: How to Use Your Remaining Vacation Days

2 thoughts on “Vacation Days and the PTO Hustle…

  1. I love this! Particularly since I’m a person who is typically all or nothing- meaning if I can’t go on a long whopper of a vacation, I can’t go. This shows that I have so many options. And now I’m thinking about how I can do a bunch of weekend trips over the next couple years!

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