How to stop overplanning your vacations

Here are 15 tips that helped me do just that

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #47. ✨

Vacation snack, captured on Kodak Portra 400 film

Two weeks ago, as all the familiar symptoms began stacking up—sore throat, chills, congestion—I realized, with a sinking feeling, that I was getting covid on vacation.

I was lucky to be visiting family in Maryland, which meant that my isolation period included my dad’s homemade chicken soup delivered to my doorway (and, crucially, zero extra hotel expenses when I had to delay my return flight).

The second blow happened the day I came out of isolation.

My phone’s Airbnb app pinged me with a notification: the booking for my long-awaited summer trip had been canceled, meaning that my first post-covid order of business was scrambling for replacement lodging in rural British Columbia, one disrupted travel plan flowing directly into another.

In a previous life, either one of these developments would have caused a minor freakout. In my twenties, every trip I took was planned to the hilt, with a detailed itinerary I’d designed to avoid wasted time and disappointments.

But while I was devastated to cancel get-togethers with my D.C.-area friends, everything else just…worked itself out. My canceled Airbnb—the dreamy one with its backyard sauna? I found a new one with an ocean view. My covid diagnosis? Salvaged by everything I did pre- and post-virus.

My mid-Atlantic highlight reel

My ability to roll with the punches while traveling hasn’t come naturally, or by accident; rather, I’ve actively developed an approach to travel planning that allows me to embrace uncertainty. With summer travel on the horizon, it’s an approach I want to share with you.

Here are 15 practical tips for implementing a more Goldilocks approach to travel planning: not too little (that’s just stressful), not too much (that’s rigid and exhausting), but rather a balance that feels just right.

1. Consider not leading with the destination.

For years, I picked my preferred destination—Lexington, Portland, Milwaukee—then organized a trip around it. It’s how most people travel! But these two alternative approaches tend to put me in a more spontaneous frame of mind:

• Decide what you want from the trip first. Pick a location based on that. Earlier this year, I needed a restful weekend away. So my boyfriend and I visited Victoria, mostly because a floating spa had just opened in the city’s harbor.

• Find an amazing flight deal, then build a trip around it. I got this idea from Scott Keyes’ book Take More Vacations: How to Search Better, Book Cheaper, and Travel the World. Picking a destination based on a searing-hot flight deal makes you feel adventurous, and like you’ve already won: a recipe for maximum chill.

2. Instead of researching everything, think about gathering context.

That way, when you land in a new place, you’ll still have scaffolding to hold any information you gather on the ground. Context also informs where you decide to wander: when I visit Scotland later this year, I’ll want to know which of Edinburgh’s neighborhoods cater to tourists versus locals, and which are more historic or modern.

Remember: you can gather context in creative ways. I’m currently reading

Jo Piazza

’s The Sicilian Inheritance, which strikes me as the perfect novel to devour before a trip to Italy. Substitute Midnight in the Garden of Good and Evil before going to Savannah, or listening to Françoise Hardy before heading to Paris…the options are endless.

3. Find a container for your research that isn’t an itinerary.

My own favorite container, and the closest thing I have to a travel hack, is a tool called Google My Maps, which works especially well when visiting someplace walkable.

Here’s how it works:

1. Create a new map before each trip, dropping pins on any addresses you’re interested in visiting.

2. If it brings you joy, you can group the pins by category (restaurants, breweries, museums, trailheads, your Airbnb or hotel address), color-code them so they’re easy to identify at a glance, and add notes to each pin to include operating hours.

3. When you’re on the ground, open the Google Maps app, navigate to My Maps using these instructions, and easily spot what’s nearby—and open.

This is my favorite tactic for a few reasons:

• Before a trip, it allows me to enjoy the dopamine boost of travel research, discover which neighborhoods sound appealing, and save details that would be annoying to look up on the go, but without plotting out each moment of my trip.

• While I’m away, it allows me to wander and stumble upon places organically. But if I don’t find anything, I have a fallback option close by. I use Google Maps to get around, so it’s helpful that my research “lives” there, too.

4. Research things that would be points of friction, frustration, or stress on the road.

For me, that means lodging, transportation (here in the Pacific Northwest, that includes ferry schedules!), and international cell coverage.

But everyone’s different; you might love leaving a few nights hotel reservation-free, in case you want to decamp to a new location. And some seasons of life require extra contingency planning, as anyone traveling with kids already knows.

5. Apply your planning powers to anything dull or repetitive.

It took a decade of adulthood before I found a solution to the panicky feeling I get the night before a trip: have a template packing list on hand.

Now, instead of having to remember to bring a backup pair of contact lenses every time I leave home, that information is safely tucked into a reusable Google Keep checklist. That’s an appropriate application of my Type A personality.

6. Bring the resources that help you enjoy spontaneity.

When I’m starving, waiting for a restaurant table sans reservation isn’t fun, it’s rage-inducing. The easy solution is to have the adequate resources on hand—in this case, snacks!—to avoid getting to the low blood-sugar state where spontaneity stops feeling enjoyable.

If you’re traveling with kids, your resources might also include various forms of entertainment to avoid in-air meltdowns. (Cue the nostalgia for the Mad Libs and Invisible Ink books of my youth!)

7. Protect the margin.

When each day isn’t crowded with plans that only make sense on paper, you allow for detours, wrong turns, and surprises—all of which are inevitable, but can either be anxiety-inducing or exciting, depending on how much free time you have.

8. When applying structure, consider the timeframe.

For example: you might not want a two-week trip to pass with zero structure, but building excessive structure into any single day probably feels too rigid. With a bit of experimentation, you’ll find a happy medium between the two extremes.

Speaking of experimentation: if you’re an uptight traveler, try all of this on shorter trips first. The stakes feel lower on day trips or long weekends.

9. Deploy a healthier form of structure.

If structure and planning are your security blankets away from home, you don’t have to go cold-turkey. Bring some of your daily routines on the road, or create special ones just for travel.

I’m partial to

Brenna

’s chill framework for a good vacation: “Go on an adventure, settle in for a coffee and a pastry, and explore a cultural event.” Another one that works for me: each day, commit to no more than two activities, one being defined by adventure or movement, and the other defined by slowness or rest.

10. Talk to other humans.

Over an otherwise forgettable lunch in Victoria, I asked our (very cool) waiter about his favorite place to eat. He pointed us to the best meal we had that weekend: a tiny restaurant in a hidden courtyard, one that never popped up on Yelp.

11. Detach from your phone.

Conveniently, smartphones bundle dozens of functions into one device. But there are unintended consequences: being hyper-connected when you want to disconnect, and not engaging with your surroundings. You know, all the stuff that bumps you out of experiencing mode and back into planning mode.

So use your phone as a phone, but consider which other functions you might want to substitute for the real thing. Use a camera instead of your camera app, read paperbacks instead of scrolling the Kindle app, or—I’m serious—consult a road atlas for long car trips. (Does anyone really need turn-by-turn directions on a hundred-mile stretch of highway?)

12. Remember that being bored isn’t an emergency.

Actually, boredom has upsides: it’s the state that precedes acclimating to a more natural pace of life. It also spurs creativity, connection, and rest. More good reasons to stop overstuffing your itinerary!

13. It’s okay to be disappointed.

Ironically, many joyless travel experiences start when we try to squeeze Peak Fun™️ into every waking moment.

When you stop trying to force enjoyment, your worst fear will come true: you’ll be disappointed more often than you’re used to. But allowing room for disappointment leaves room for the possibility of being surprised and delighted beyond your wildest expectations. Peaks can’t exist without troughs.

14. Consider a break from “recommendations culture.”

I love reading a well-curated list of recommendations as much as the next person. But there’s a fine line between using them as menus to pick and choose from (lovely!) and to-do lists (…less so).

You may have noticed that these lists can collapse into an aesthetically-pleasing but eerie sameness. I’ve visited countless hipster coffee shops in new cities only to be met with a profound sense of déjà vu.

I usually cling to recommendations culture when I’m worried about being disappointed (see #13). But when I allow myself space to be disappointed, I start looking for recommendations offline (see #11) by talking to real people (see #10), which usually leads to less Instagrammable—but more meaningful—experiences.

15. When it’s over, enjoy the feeling of wanting more.

When you leave a “must-see” sight unseen, it’s not a failure: it’s a reason to return. Ending a trip not having done everything—being left wanting more—can be a beautiful thing, if you let it.

💬 What do you think?

I’m curious to hear from you. What helps you slip into a more spontaneous frame of mind away from home?

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie