Tech Tools to Help you Plan (And Enjoy) Your Next Vacation

Summer for me means baseball, and baseball for me means rooting for the New York Yankees. Growing up, my grandpa (a fellow Yankees fan), liked to poke fun at Yogi Berra quotes. We both knew the phrases were ridiculous or painfully obvious. But sometimes, in all his simplistic wisdom, Yogi managed to hit the nail on the head and his words were the appropriate maxim for the situation at hand.

As I was looking at the calendar and trying to line up my own summer vacation plans, I couldn’t help but think of Yogi’s line, “If you don't know where you are going, you'll end up someplace else.” 

Turns out, American workers didn’t quite know where they were going when they started down the path towards America’s Lost Week. They thought they were working harder, better, and faster. They thought that this idea of always being on was making them more productive. In reality, workers across the country are hurtling towards total work martyrdom.

One thing we know with certainty is that planning time off is the single most important step you can take. Yet more than half (51%) of households never take the time to plan a vacation. We keep trudging along through the work week, not knowing where we’re going or when we’re going, and before we know it, it’s the end of the year and we haven’t used a single vacation day.

The funny thing is, we set out with good vacation intentions. The first time we measured vacation day usage, we conducted the surveys mid-year, which required respondents to consider the amount of time off anticipated. Back then, we reported Americans left 429 million vacation days unused. For our latest State of American Vacation 2017 report, conducted in the fall of 2016, required that respondents know exactly the amount of time they used in 2015, painting a more accurate picture. Americans left 662 million vacation days on the table. In other words, there's a (not so great) gap between our intentions and reality when it comes to taking vacation time.

So how do we actually #TakeADay? Could technology—the very thing that we know is largely responsible for us taking less vacation time since 2000—be part of the solution?

I’ll go out on a limb and say yes. Sure, it’s a little backwards that we’re relying on the very thing that prevents us from taking time off in the first place to get us back on track. But like a choice Yogi-ism, it’s just crazy enough that it could work.

There are a number of apps and sites that help provide antidotes to all the reasons why we avoid vacation, whether it’s the fear of returning to a mountain of work or feeling like we can’t afford a vacation. 

Here are some tools that will help you plan (and enjoy) your next vacation: 

1. For Planning Out Your Days Off
For starters, let's get a little old school with the steadfast calendar. Open up your Google Calendar, grab a pen and your planner, whatever you use, and plug in the following reminders for yourself throughout the year: annual review of your company's vacation policy; quarterly check-in on how much paid time off you've used and how much you have remaining; quarterly vacation planning sessions; deadlines for booking flights and travel arrangements; and of course, blocks of time for your actual vacation(s).

For the next leg of planning your vacation, apps such as TripIt, TripCase, and Roadtrippers can help you plan your trip itself, and keep track of itineraries, confirmation emails, and more. To navigate your final destination, create a custom Google Map. You can color-code and group locations on the map by categories such as "Places to Eat," "Sites to See," or other customizable layers. Plus, if you're traveling with friends or family, they can also add points of interest to the map. All you have to do is sign into your account on Google Maps (iTunes, Google Play) to access your custom map from your phone. 

2. For Setting a Vacation Budget
Thirty percent of American workers say they don't feel like they can financially afford to take a vacation. Crunching numbers isn't our favorite activity either, and figuring out how to finance a trip or even a staycation can be daunting. But there are plenty of sites and apps to help, starting with Huffington Post's Take A Break Budget Worksheet. The worksheet will take you through your vacation expenses line item by line item so you know exactly how much you intend on spending and can stick to it. Sites such as Google Flights, Kayak, Hipmunk, and more can help you save money on travel arrangements and accomodations.

3. For Communicating Your Time Off
The number one reason Americans give for not taking vacation? The fear of returning to a mountain of work. You'll undoubtedly have some catching up to do after taking time off, and deciding how much you want to remain plugged in on vacation is your decision. Before you leave, set expectations with your team, whether it's that you'll check email once in the morning or evening, won't be checking at all, or would prefer to receive texts for truly urgent matters. Then set up an out-of-office reply so that everyone is on the same page about how long you'll be gone for, who to contact in your absence, and if and when you'll be checking messages. Your crafty out-of-office message might inspire others to #TakeADay, too. 

4. For Taming Your Work While You're Away
Once that out-of-office is ready to roll, you have plenty of tools at your disposal to help manage your emails on vacation that don't include deleting your account altogether (though removing your email from your phone temporarily is also an easy fix). Apps such as Inbox Pause, Mailstrom, and Sanebox can let you snooze emails while you're away, and filter them to manage any temptations to check and respond to the non-urgent stuff. For those who want a total internet blackout while on vacation, apps such as Freedom, Flipd, Cold Turkey, and OFFTIME will make you forget you even have a phone. Want to disconnect on your vacation? Flip on airplane mode so you can still use your camera to capture memories.

Ultimately, technology can be part of the solution to taking back America's Lost Week. Much like we adapted to using technology over the past decade to make our work lives easier and more productive, we can also adapt to making tech a part of successfully taking our time off. All it takes is a little effort and setting boundaries.

Note: The data and statistics referenced in this post have been updated since we originally published this post. Learn more about the State of American Vacation 2017.

July 13, 2016