How you plan and organize your trip says more about you than you think

Jan 14, 2020

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The way I see it, there are two types of people in this world: People who show up for a trip, and people who show up for their trip.

Personally, I have a borderline obsessive methodology for planning a vacation. I plan my trip around where I’m eating, and will spend countless hours researching and cross-checking the best spots from various reviews and social media platforms.

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Then, you have someone like my mother, who used a pen and paper to organize her trip to Barcelona and Amsterdam this summer and called it a spreadsheet. Yes, she’s the cutest.

Related: Where you should travel to this year, based on your Myers-Briggs type

Since we know you’re all actively planning out your 2020 travels (and, for some of you, an entire decade’s worth of trips) we decided to look at some of the various strategies travelers have for organizing itineraries. Here’s what your spreadsheet, notepad or spontaneous “anything goes” attitude say about you.


There’s no way around this one. You’re Type A through and through, and you don’t settle for anything less than absolute perfection. The thought of not abiding to a schedule by the second makes you break out in hives. When you’re not traveling, you’re the one in your family or group of friends who makes the restaurant reservations. Since we know you like to plan ahead, set an award alert so you know precisely when availability opens up. You can add it to your spreadsheet after.

Senior reporter Katie Genter uses Google Sheets to keep track of hotels reservations, flights and other important bookings. That way, the details of each segment and the confirmation and booking numbers are all in one place. While it might have been stressful planning it all out, you know putting your itinerary in a hyper-organized spreadsheet with functions that automatically tally your current points and miles balance will make the entire trip seamless.

Word document

Using a Word or Google document makes it easy for you to keep everything in one place … and save it in a folder on your desktop with all the other odds and ends you need for your vacation. You probably have a 10-step skincare routine but frequently lose your AirPods.

If you’re using Google Docs, you’re likely planning a group trip, so you need an easy way to share recommendations and collaborate with your companions. If you’re organizing your trip with Microsoft Word, we have a feeling you’re something of a traditionalist. Since we know you’re probably going to stay in a chain hotel, make sure you’re getting extra bonus points for it. Win, win.

Google Maps

You like to fly a little bit below the radar — after all, Google Maps may just be the most underrated way to plan a trip. When you’re not planning a vacation to the other side of the world, you’re likely setting calendar alerts so you never miss an appointment. You recently Marie Kondo-ed your apartment and you’ve never been prouder.

TPG reporter Liz Hund swears by this method, and typically organizes her itineraries with color-coded pins tracking the restaurants she wants to try, for example, and attractions she wants to see. This helps her visualize what locations are in close proximity to each other, and helps her better organize her vacation. Plus, you can easily share it with all your friends and family afterward.

Notes app

You thrive on structure and prefer to have all of the details mapped and planned out, but know you need to give yourself a little wiggle room for the inevitable delay or travel mishap. You want to be able to change your itinerary if necessary, so you don’t like things totally set in stone. More likely than not, you’re a big fan of the solo trip and firmly believe everyone should do it. (They should!)

Wallace Cotton, TPG’s community manager (and arguably one of the biggest AvGeeks in the office) said he uses his Notes app to track travel plans and added, “It’s not creative, but it gets the job done.” While you don’t necessarily need the fanciest or shiniest things around, you like to have flexibility. After all, what happens if you see a place pop up on Instagram that you just have to see in person?

Pen and paper

You can’t be bothered with technology, and that’s OK. You have a trusted travel agent who you’ve been using for years, and you want to step up your points game to make a trip to New York since the TWA Hotel isn’t going to see itself. You may even have your frequent flyer number from Continental Airlines stashed away somewhere.

Less flexible than the notes app but a similar sensibility, using a good old pen and paper can help you remember what activities and attractions you want to prioritize. Let’s just hope you remember where you put that Post-It.


You like to live life on the edge. You’re the, “We’ll cross that bridge when we see water” type of person, and you know what? That’s great.

You’ve been known to plan a last-minute trip from time to time (who can resist a cheap deal to the Caribbean?!) and have Google Flights bookmarked to check flight prices to, well, anywhere, on a whim. Pro tip: Get a card that earns you bonus points for airfare purchases, so even when you go to book a last minute flight, you’re earning valuable points and miles that you can use on your next one.

Featured photo by estee janssens/Unsplash.

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