How to Plan a No-Stress Road Trip With Your Friends

Saddle up.

By Phoebe Neuman
picnic on the beach // Entertaining with DeNai Jones

When one of my closest childhood friends announced she’d be driving across the country this summer, I jumped at the chance to join her for a road trip — as did two of the other members of the girl group we ran with in high school. Though none of us had spent more than a weekend together since graduating (and currently live in four different states), we fell right back into those familiar ways of being together. And somehow, we managed to pull off a four-night road trip from Seattle to Jackson Hole without a hitch.

Along the way we learned a lot about the adult version of our relationships — and that some things, like giggling all night with your closest friends, never get old.

So if you’re thinking about planning a road trip with your friends, my first tip is to just do it! Dive in and do what you need to do to make it happen. Things may not go according to plan, but if you keep the following tips in mind, I guarantee you’ll create those laugh-until-you-cry memories that will last a lifetime.

image by daniele rose photography


image by goop

Be Honest

Beyond simply booking the tickets or requesting time off, my biggest tip for a smooth-sailing road trip is to be completely honest with your friends. It’s the only way to make sure everyone’s expectations are aligned before you hit the road. Otherwise you may end up with one person who thinks the crew will be dining out at 5-star restaurants every night and another who’s budget only allows for cheap eats.

Before you pile into the car, get everyone on the same page including their max budget, if they have any non-negotiables on the itinerary, and if there is anything that they absolutely don’t want to do. (Mine was car camping. I’m a hotel and AirBnB kinda gal, and there’s no shame in owning up to it!) That way, everyone can know what they’re getting into before the planning gets underway.

What to pack when you're traveling

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Designate a Map Maven

One of the easiest ways to get frustrated during the planning process is to let too many cooks into the kitchen. Once you have a basic idea of where your trip will begin and end, assign just one person in the group to map out the rest of the major stops on your road trip.

If you’ve already set expectations, it should be relatively easy for your navigator to figure out the spots that hit everyone’s list. Have her map a couple of routes, including the number of nights spent in each, and then take a vote — the most popular pit stops win.

computer, office, home, reading

image by steven simko

Google Drive is Your Friend

After you’ve gotten your stops mapped out, it’s time to fill in the itinerary. And the easiest way to get the brainstorm going is to set up a shared document or sheet in Google drive. Have your route master outline each destination, and then ask everyone list all of their ideas under each place.

Once everyone has detailed their must-try restaurants, Instagrammable sites, and can’t-miss shops, take a look at which ones come up across multiple lists. If more than one person wants to do it, consider it part of the itinerary. Or, if you’re really organized, you can drop everything into a table with columns for the sites/stops and each person’s name. Then have everyone mark what they’d like to do with an agreed-upon symbol — the cafes, hikes, and boutiques with the most votes should be at the top of that itinerary.

fun girls night idea

image by kate zimmerman

Go with the Flow

That all said, don’t be afraid to throw the plan out the window when the occasion calls for it. If the group decides they want to spend an impromptu day brunching and lounging instead of the scheduled museum hopping, don’t sweat it. If the drive takes two more hours than expected, don’t worry — you’ll have more than enough time to explore the next stop anyway. Taking this live-in-the-moment approach will keep everyone from becoming frustrated when things aren’t going as planned, and will keep you focused on what you’re really there for: spending quality time with each other!