Bookmark these must-have digital tools to plan your next vacation

October 15, 2019
Category: Tech & Tools

This article originally appeared in Try This! — Tools for Journalism, our newsletter about digital tools. Want bite-sized news, tutorials and ideas about the best digital tools for journalism in your inbox every Tuesday? Sign up here.

If you’re reading this, I’m on vacation somewhere in Rome, likely shoveling cacio e pepe into my mouth as the waitstaff gasps in horror.

If you’re wondering how a digital tools reporter travels the world, you’re in luck. I’m not quite Inspector Gadget (I’m still searching for a helicopter hat), but I have amassed a Swiss Army knife of technology to augment all aspects of the travel experience — from finding and booking trips all the way to the return trip home.

Here is a special double edition of Try This! that highlights the best apps, tools and tech tips for travel, all carefully tested and personally used by yours truly.

Finding and booking a trip

I employ two disparate strategies to book flights on the cheap. The first is to keep an open mind and buy tickets to wherever is inexpensive (and appealing — we’re old friends, Rochester, but I don’t want to vacation with you). The second is to pick a destination and wait until a good deal rolls around to book it.

Skyscanner is a top tool for either strategy. Pick your home airport and where you’d like to go, and Skyscanner will pull up a calendar that lists departure and return prices for each day (Google Flights offers similar functionality). Alternatively, pick a departure airport and list “Everywhere” as your destination and Skyscanner will create a list of the cheapest places you can fly to.

If you’re more of a wait-and-see type, or if you don’t want to scour those sites for cheap flights every day, there are a handful of email newsletters that surface good deals and send them directly to you. I’m signed up for Scott’s Cheap Flights, Matt’s Flights and FareDrop, and have booked some astoundingly good flights from them. Scott’s and Matt’s are free but offer robust paid versions. FareDrop costs $50 a year but is more customizable than its competitors.

All of them can save you a load of dough. As an example, I’ve snagged flights from Miami to Paris for less than $300 and to Rome for less than $400. Both cost double that on a regular day.

And since you’re saving a couple hundo on plane tickets, consider reinvesting some of that dough back into the planet. I recently started using Cool Effect, which has been recommended by The New York Times, to offset my carbon emissions. Cool Effect distributes the money you donate to environmental organizations that replant trees, distribute fuel-efficient stoves to parts of the world that need them, and pay for protections for endangered areas. You can also just use their carbon calculator to decide how much to donate to your environmental charity of choice. You can take as many vacations as you can afford, but there’s only one Earth.

Planning a trip like a digital pro

Once you’ve got a flight booked, it’s time to dig into what you’ll actually do there. This, my friends, is the best part.

Any good trip is a balance between rigorous planning and allowing serendipity to hand you your next favorite travel memory. I like to start with a list of all the things that I’m interested in (more on how I actually do that in a minute). It typically includes the Big Sites — the Eiffel Tower, the Colosseum, three separate statues of small beings relieving themselves — and a few in-the-know stops from friends and family. Then I prioritize that list and assign one or two things to each day of the trip. This involves a lot of resisting temptation to pack the itinerary and a lot of self-persuasion about how it’s OK to let the rest fall off. That, my friends, is the worst part.

From there, I gather information about anywhere that seems interesting. A few regular sources:

  • Atlas Obscura, a site that catalogs interesting places around the world, offers a map that includes all of its beautiful and bizarre locations.
  • The Washington Post’s By The Way guides to cities around the world are indispensable. If you’re interested, I wrote about how it’s different from other travel sites.
  • Instagram is a goldmine. Search hashtags for #[yourdestination]travel or #[yourdestination]food for awe-inspiring and mouth-watering photos (just be prepared for those places to be overrun with other tourists).
  • Airbnb isn’t just for lodging. The site also offers a “things to do” section that allows you to book, erm, things to do. Even if you don’t use Airbnb to book lodgings, it’s a good way to see what’s out there. Viator offers similar features.
  • La Liste is an app with a restaurant list curated by some of the world’s best chefs (in addition to the crowdsourced lists you’d find on other apps). If you’re looking for truly local restaurants, look for those in which the online reviews seem to be mostly written in that country’s native language, or try searching for the city’s name and terms like “hidden gem,” “local favorite” or “locals only.”
  • It’s not for people with little patience, but YouTube travel vloggers often surface miraculously weird and wonderful things to do in the places they visit. Think about it: They’re trying their hardest to stand out, so the impetus to find new classics is high. I like Kara and Nate (the creators of FareDrop) and The Endless Adventure.
  • Oh, and ‘tis the season to see fall foliage in the U.S., so here are the best places for that.

This is where the tech stuff comes in. TripIt and App in the Air are both adept tools for keeping track of your flights and reservations. Both offer the ability to scan your inbox for information and automatically adding it to your itinerary, but I’d caution against that if you use that email account for anything sensitive (and even if you think you don’t, you probably do). Instead, I typically just forward my emails to them as they come in.

Both tools combine all of your bookings into one itinerary, both can automatically add that information to your calendar of choice, both automatically update that information if flights change or plans get canceled, and both offer quick and easy-to-parse interfaces for when you panic about your departure gate in the middle of the airport. Both also offer paid versions. App in the Air Premium is cheaper than TripIt Pro and offers more features — automatic check-ins, airline reviews, seating advice, expected wait times for security, fun badges for mileage and more.

Neither can effectively keep track of your non-ticketed plans, though, and that’s where Google Docs and Google Maps come in.

My friends think it’s extra (and it is), but I create a fresh Google Doc for every trip. I start with dates, destinations and travelers. The itinerary starts taking shape with flights, then I fill it in with reservations. There’s a section where we drop ideas about things to do on a list. Once we decide which of those are must-do’s, they find a place on the itinerary. There are sections to list the average weather, to track whether we have access to clothes washing machines throughout the trip, to compile costs, to sort out who will watch our pets and a to-do list as we approach the date of travel.

All locations with an address make it to a Google Maps “my map” (here’s a sample map from a recent trip my friends and I took to Nashville). When someone gets hangry, we can consult the map for a quick, vetted restaurant recommendation. If we decide to chill in a neighborhood, we can see what’s interesting around us. Or we can just ignore it and let our feet and eyes decide for us. The map functions as training wheels — there if you need them, easy to remove and ignore if you don’t.

Prepping for the journey

I’ll admit it — I’m that weirdo who loves the actual travel part of a vacation. Packing is like an IRL version of Tetris. Flying? It’s a miracle! You’re six miles above the ground in a 175,000-pound tube and someone is giving you a TV dinner and cheap wine while you’re marathoning movies.

You’re probably not like me. So here’s a little help.

The New York Times built a stellar guide on how to pack a suitcase. In general, buy slightly smaller luggage than you think you’ll need, lay out all of your items before you pack and edit them like you’re editing your writing and use techniques like rolling or tools like travel cubes to keep everything compact.

The Times recommends a 5-4-3-2-1 formula for packing (for a five-day trip, pack five undergarments, four shirts, three pants, two pairs of shoes and a hat. Your mileage may vary on that (ba dum tss) depending on your destination and usual style of dress. You’ll also obviously need to pack things that aren’t clothes. Here’s a remarkably thorough list for that.

If you’re a gadgety type, Wirecutter has a fantastic list of gizmos and thingamabobs to make your vacation a little bit easier, from suitcases all the way down to undies. I’m testing the travel clothesline during this trip and I know you’re all on pins and needles about my review.

Then there’s the work angle. As I write this, the week before I leave, my to-do list has grown so massive that it risks blocking out the sun. If you’re a freelancer, Creative Boom has some great advice for prepping for a vacation (and a logo with moving eyeballs that I played with for 10 straight minutes). It’s tremendous advice for anyone, really. If you’re a manager or business owner, Look and Feel Branding also has some solid advice to follow (which, again, can be useful for almost anyone).

Not coincidentally, both emphasize unplugging while you’re there. My first task after making it through airport security is to turn off all of the notifications and badges for my work apps. You could also drag them all to an out-of-the-way folder or delete them outright. Just get them off your homescreen and out of your notifications. You’re traveling to re-energize and avoid burnout — you can’t do that if you’re carrying the source in your pocket.

Hitting the skies

My body tweaks out when I fly from Florida to New Orleans, let alone somewhere with more than a one-hour time zone difference. I’ve always assumed the solution to jetlag is either pharmacological or to just smile through the exhaustion and be happy that I’m privileged enough to fly so far from home.

But there’s an app for that.

I’m currently testing Timeshifter, an app that creates a personalized itinerary for beating jetlag. Its recommendations begin three days before the flight — with tips on when to start and stop drinking coffee, when to expose yourself to and limit bright light, when to head to bed and even when to pop a melatonin. My compatriots for this trip have been skeptical, but it has to be better than nothing. I’ll update you with results.

Sleeping in the airport is another great way to mitigate jetlag. There’s no better place to catch a quick snooze than in a comfortable and relatively quiet airport lounge, but who has the dough for that? You might. Kara and Nate, two of the travel vloggers I mentioned, put together a guide to accessing airport lounges, even if you’re not a high-flying business class type (signup required; they’ve never emailed me). And of course there’s an app for that, too. LoungeBuddy tells you what it takes to get into airport lounges around the world and whether they’re worth the cost.

Airports seem to be improving the quality of their restaurants and amenities all the time. The trick is finding the good stuff when you’re on a time crunch and an accessible set of golden arches is right there in front of you. Trippie is the invisible hand to guide you from fast food to good food.

If you’re traveling into or out of the U.S., the Global Entry program allows you to skip through the customs lines. But it also costs $100 every five years and has a massive wait time in many parts of the country. Use the Mobile Passport app to get the same customs benefits (sadly, it doesn’t help with that whole TSA process like Global Entry does) for the low price of free.

When you’re there

At this point, I’m mostly going to leave you to take your own vacation.

But it wouldn’t be a Try This! newsletter if I didn’t grouse about digital security. On Medium, The New York Times is back with advice about how to protect your phone when you travel. Turn on Find My Phone/Device and consider sharing it with a loved one back home. Check with your carrier about data charges and insurance. And put emergency information on your lock screen.

They don’t list it here, but consider using a VPN if you’re traveling to a country that monitors traffic or blocks websites. TunnelBear is easy to use and will only cost you $10 for a month.

If you’ve mapped out your trip or plan to use your phone’s GPS to get around, use Google Maps’ download feature to limit your data usage and reliance. You can either navigate to the “Offline maps” section of the app by tapping ≡ on the top left of the app, or download a map you’re viewing by typing “ok maps” into the search bar (h/t @starsandrobots for that cool tip).

There is one other app that blows Google off the map. It comes with three big “ifs.” If you’re traveling to one of 40 major cities, if you have a reliable data connection and if you can handle an app that loves to drink down your phone’s battery, CityMapper can’t be beat. It can tell you how to get anywhere in a city, through just about any means of locomotion, and how much time each will take.

And let’s dispense with the farce. Even if you don’t post it to Instagram, you know you’re going to snap pics of your food. Here’s The New Yorker’s Helen Rosner on how to take pretty pictures of food.

No matter where you go and what you do there, whether it’s a staycation under the covers or a multinational trip across the globe, make sure you’re taking the time you deserve to care for yourself. Travel is optional, but a little R&R every now and then is paramount.

Ren LaForme is Poynter’s digital tools reporter. He can be reached (in a few weeks) at ren@poynter.org or on Twitter at @itsren. 

Try This! is supported by the American Press Institute and the John S. and James L. Knight Foundation.