Financial Literacy

How to Plan A Perfect Vacation Trip: 7 Easy Steps

ACTION STEP: Take Time Off Work

The difficulty of requesting vacation days varies from job to job. However, you can make the process simple for you and your company by using some good old-fashioned scripts.

Oh, look, here’s one now:

Subject: Vacation request (October 2nd through October 6th)

Hi [manager’s name],

I’d like to request vacation time from Monday, October 2nd, through Friday, October 6th, because I’ll be taking a family vacation over those days.

While I’m gone, I’ll be reachable by phone but not by email. I’ll be making sure that we have coverage in the support queue. I’ll also be distributing a playbook to my team so it’s clear who owns which issues.

Is this OK?



This is a great script to use, even if your vacation is during a busy time for your company.

Why? First, consider why your boss might want to deny you vacation time:

  • You own a project, and it might not get done while you’re gone.
  • The work might end up on your boss’s plate.
  • Your boss might have to delegate YOUR tasks to other workers (which nobody likes doing).

This script addresses all of these points in the last paragraph. By showing that you’ve gone the extra mile to make sure that your responsibilities will be taken care of in your absence, you allay your boss’s concerns that your work won’t get done.

It also maintains a friendly tone throughout the message AND you give a good reason for your absence. You’ll want to send this email weeks, possibly even months, in advance. It’s far easier for your boss to say yes when the company has time to plan for your absence.

For more information on requesting time off, see my article on how to ask for vacation days.

Step 4: Find Affordable Flights

One of the most common misconceptions about traveling is the idea that flying (especially internationally) has to be expensive.

I have my thoughts on this… but I’ll let celebrity chef Gordon Ramsay take it from here:

“In fact, flying can be one of the most affordable parts of the trip if you know how to leverage the right tools.”

Two of the most effective tools to find affordable flights are:

  1. Travel credit cards
  2. Repositioning with error fares

Let’s take a look at both now.

Travel Credit Cards

We’ve written about travel credit cards before, but it bears repeating:

Using travel credit cards to pay for flights is a Big Win.

Say a round-trip flight from New York to Paris costs $500.

If you book using the card we’re about to suggest, you could get that same flight for FREE.

You can save THOUSANDS each year if you leverage reward points. And the more time you have to plan, the more points you can amass. Many cards even give you sign-up bonuses.

But with so many options out there, which one should you get?

For more information on travel credit cards as well as how you can maximize them, be sure to check out my article on the subject.

NOTE: If you’re in credit card debt, DO NOT sign up for a travel credit card… or any other credit card for that matter. Instead, check out my article on how to get out of debt fast.

If you’re nervous about getting into travel hacking through credit cards, that’s okay. There’s another solution that’ll help you find ridiculously cheap flights.

Repositioning With Error Fares

I’ll give it to you straight: Airlines really mess up sometimes.

Sometimes their mishaps lead to some great deals for you through error fares. Error fares are airline tickets that are, temporarily, a WAY lower price than they’d normally be (typically through technical or human error). These fares often mean travelers can get tickets from the mainland U.S. to places like Europe and Asia for a few hundred dollars or less.

To find these errors and deals, several websites are dedicated to hunting them out.

Here are a few that I suggest you leverage the next time you’re looking for flights:

  • Secret Flying. This site immediately posts any errors or deals it finds. You can even use their handy search function and enter your country of origin and destination so they can find a deal more suited for you.
  • The Flight Deal. Another great site for finding amazing deals on airfare as well as hotels, rental cars, and travel credit cards. They also give you information on flight deals happening in almost every major U.S. metro area.
  • Scotts Cheap Flights. A tried-and-true resource when it comes to finding error deals. Scotts offers a free newsletter that’ll notify you whenever they find a deal, along with instructions on how to book it.
  • Next Vacay. This is Naveen’s very own site that helps travelers find the best deals. Next Vacay automatically crawls through various airfare sites to find you the cheapest flight possible.

One key thing to remember when purchasing an error fare:


You’re taking advantage of their mistake. If you point out how they messed up, they’re going to realize it and not let you have the deal. Stick to booking through the sites above or third-party sites like Skyscanner instead.

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