How to Ultimately Finesse your Vacation Days


I hear people say it all the time, “I don’t get to travel because I only have 1 week of vacation a year.” Or, “I cant go overseas because the flights are too long and I would need to go for at least a week at a time...” Well, allow me to break those barriers:

Hack #1: Travel to locations with the shortest flights first

So, you want to travel, but maybe you’re not ready to hit China on your first vacation. For those of us on the southern states of the US, I would suggest venturing to places like; Central America, Mexico, the Bahamas, the Caribbean, South America and maybe Hawaii. To give you an idea of how short a flight can be, I’ve added some examples below:

DFW – Rio de Janeiro

DAL – San Jose, Costa Rica

LAX – Peru

LAX - Cancun

Sacramento – Hawaii

Orlando – Jamaica

Orlando – Colombia

New Orleans – Nassau

SATX – Santiago

So as you can see, traveling to nearby countries first will allow you to make the most out of a 3-day weekend trip – you’d no longer need to waste a full week in fear of a long flight. Once you get up to more than 5 days a year, then we can talk about those adventures that call for 1-2 day flights. More on that later though.

Hack #2: Travel on the weekends

For those of you who have the weekends off should already know better. By traveling on the weekends you get an extra two days of vacation or travel – depending on where you’re venturing off. And get this, it’s the easiest way to get a week-long vacation (use 3 out of your 5 vacation days, and BOOM! One week vacation here we come). Here are some suggestions of places I would travel with 5 days off.

From DFW or anywhere on the East Coast:

  1. Peru

  2. Rio

  3. Portugal: Porto, Lisbon, Sintra

  4. Spain: Madrid and Valencia or Barcelona, Bilbao

  5. France: Toulouse, Marseille, Monaco or Paris and Caen

  6. Morocco

  7. London

  8. Ireland

  9. Italy

Hack #3: Travel over the holidays – aka FREE vacation days

Most companies will give you anywhere from 3-6 holidays off, this is perfect for any Wanderer. I always try to leave the day of a holiday rather than the day before; flights are cheaper since mist people try to already be home for the holidays. The only downside is, depending on the company you work for, you may not get paid on that holiday if you travel the day before the actual holiday. OR, if you're lucky, you will get reimbursed your vacation day if you take vacation on a holiday you're already off. This is how my company works so it allows me to travel as much as I can during the holidays year-round.

Hack #4: Split your week of vacations days into 2-3 weekend getaways or one 5-day trip and two 3-day weekend getaways/ one 4-day trip

This is extremely important; if you only have 5 days or so of vacation a year, don’t use it all in one sitting. We work 8+ hours a day! Split your vacation days into one 5-day vacation over a holiday or weekend and use the rest for shorter 3-4 day trips throughout the year. Here's an example of how I used 5 vacation days a year to travel 3x a year at almost a week each time!:


Use 3 vacation days over Thanksgiving = 5 days off (+ 2 days over the weekend) => 1 week in Greece

Use 1 vacation day in May + May Holiday + 2 days over the weekend = 4 days in Peru

Use 1 vacation day in July (if the 4th falls on a Thursday or Tuesday) + 2 days over the weekend = 4 days in Belize


Check it out! I have now finessed my way into traveling three times a year! Now it's just time to master your travel budget. Keep an eye out for next week's article, "How to Finesses your Travel Budget"


Need help finessing your vacation days? Drop me a message on my contact me page! Don't let minimal vacation days at work stop you from adventure!

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