Unpopular Opinion: Overplanning Your Vacation Will Make It Less Stressful

Allow us to explain.

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You’re in a new-to-you city and your stomach is growling. The tour you went on finished a bit later than anticipated, and your schedule for the day has been shifted. With not much to go by, you might slip into a tourist trap or shell out your hard-earned cash for a snack that hardly makes an impression. This scenario, however, is totally avoidable—if only you planned things differently.

A recent piece in The New York Times, written by Geoffrey Morrison, disagrees. Morrison’s premise, rather, is the exact opposite: He stipulates that overplanning is what’s making your vacations more stressful than necessary. I am here to suggest otherwise. See, it’s not about planning more—it’s about planning differently.

The best way to effectively plan a vacation is to do so in a way that allows just enough flexibility but doesn’t leave you with empty pockets of time that could otherwise be used to pop into that concept shop you’ve been wanting to check out, or grabbing a gelato from that place your coworker recommended. The secret is in your Google Drive.

That is, it’s in the Google spreadsheets, docs, and, most important of all, maps that you create to document your day-by-day vacation plan, your must-see spots, and every little thing that you hope to accomplish on your trip. It’s worth it, and it’s not as intimidating a process as it sounds, I promise.

Map it out

Google maps are the most invaluable things to have when you’re traveling, and that extends far beyond using the maps purely for directional guidance. When I’m traveling, I make a Google map of my destination, and from there, I make color-coded pins of my lodging and the museums, sight-seeing spots, coffee shops, stores, and restaurants that I want to visit. In each, I write a short sentence about what the spot is and why I marked it (it’s very easy to forget which museum had that cool new exhibition and which coffee shop is best known for its cinnamon buns, after all). Don’t feel pressured to get too detailed—we’ll get into that later.

The reason why the map is so crucial is because it allows you to navigate your destination in a way that maximizes your time. When you can visualize where things are clustered, you can better figure out a plan for your day, and when hunger strikes or you find yourself with a little extra time on your hands, you can actually make the most of it: Just open up your map and find something interesting nearby!

Create your own guidebook

Okay, now comes the detail work: If you’re anything like me, at least half the fun of traveling is eating. With plenty of research, it’s easy enough to come up with a list of restaurants that pique your interest. It’s in your own best interest to organize your findings in a way that makes things simple: in a color-coded Google doc that serves as your own personal guidebook.

Your map will help you figure out where to go; your guidebook will tell you what to do, eat, or see when you get there. Found some restaurants off a travel guide? Take note of any dishes it recommended. Saw a Yelp review that recommended a specific route through a museum? Write that down! The little things are what make vacations feel special; after all, you should take any tips you can get.

Slot things in an itinerary

Now that you’ve done your homework, you’ll be far better equipped to map out your day. Make a master Google doc itinerary for everyone on your trip that includes all your flight and hotel info (this will save you plenty of headaches) and a general outline of what you’d like to do each day.

Itineraries make it easy to figure out what shape your day will take, but they are by no means restrictive, as long as you take them with a grain of salt. At the very least, they’ll help you start each day with everyone on the same foot—and if you choose to change an activity or check out a different restaurant, so be it. Even chronic overplanners can appreciate a bit of flexibility. After all, they’re prepared for anything.

See more travel ideas: Why Your Next Summer Getaway Should Be in This Quaint Southern Italian Region Better Than Instagram—7 Euro Trips to Book ASAP 4 Amazing International Hotels Worth Planning a Trip Around

Rebecca Deczynski


Rebecca is most often found digging through troves of vintage treasures, both in-person and online. Ask her to recommend a good book to read or an obscure Instagram account to follow, and you won’t be disappointed.