The Ultimate Guide to Planning a Multicity Road Trip

Taking a road trip can be life-changing — but to make sure it changes your life for the better, solid planning is key.

Plan the Best Trip of Your Life!

Is there anything more American than hitting the road, crossing the country with your playlist blasting, windows down, and a cooler full of snacks in the backseat?

Live the best of the open road. Photo by Freepik.

Whether you’re a Route 66 nostalgic or a modern explorer on the hunt for hipster coffee shops and jaw-dropping views, a multicity road trip might just be the adventure of a lifetime.

Pick Your Vibe

Before you start pinning cities all over your map, stop and ask yourself, what’s the vibe of your road trip?

  • Want to explore historic towns and eat your way through the trip? Think Southern route — Savannah, Charleston, New Orleans.
  • Into nature, hikes, and cinematic views? A western loop with stops in Denver, Salt Lake City, and Seattle might be your thing.
  • Craving beaches and parties? How about cruising the California coast from San Diego to San Francisco?

Map Out Your Route (But Leave Room for Surprises)

Build a logical route on the map — ideally in a loop so you can end near where you started. That makes returning home way easier.

Use tools like Google Maps and Furkot, but don’t try to conquer the whole country in one go. It’s better to truly experience five cities than to rush through ten without even stopping for local coffee.

Figure Out How Long to Stay in Each Spot

Don’t just spend your whole trip inside the car. Try to stay at least one night in each city — or two, or three, depending on how much you want to explore.

The sweet spot? Plan to drive between 3 and 5 hours a day. That way you enjoy theride but still have time to arrive relaxed, grab a local beer, and maybe go for an evening stroll.

Book Your Stays Smartly

Sure, you can leave a night or two open for spontaneity, but during high season or in super popular cities, it’s best to book in advance.

Platforms like Airbnb, Booking, or even classic roadside motels can add charm to your journey.

Get Your Car Ready (or Rent the Right One)

If you’re taking your own car, give it a full checkup before leaving: oil, tires, brakes, A/C — everything should be in top shape.

Renting instead? Pick the right ride for your style of trip. An SUV is great if you’re crossing states with a lot of luggage. A smaller car will save on gas.

A motorhome gives you complete freedom (and total responsibility — just saying).

Pack a Road Survival Kit

You don’t need to bring your whole house, but some things are essential on the road:

  • Phone chargers (including one for the car)
  • Snacks and drinks (yes, that cooler is key)
  • Blanket or light jacket (you never know)
  • Toilet paper and hand sanitizer (because gas station bathrooms, right?)
  • An offline map (some places are dead zones, trust me)

Get Your Playlist Ready (Or Dive Into Podcasts)

The right soundtrack can transform the whole trip. Make a playlist with classics, new discoveries, and those songs you love belting out (even if it’s just in the shower).

Prefer something more story-driven? Load up a podcast queue. True crime, travel stories, funny interviews — there’s a little something for every stretch of road.

Eat Like a Local

Before you get to each destination, do a little research on where the locals eat. Check Yelp, TripAdvisor, or even Reddit threads for solid recommendations.

Food is memory — and no epic road trip is complete without at least one unforgettable hole-in-the-wall restaurant.

Return Chill (and Already Dreaming of the Next One)

That end-of-trip sadness? Totally normal. If you can, give yourself a day to chill before diving back into real life.

And yes — once you’re home, you’ll probably be itching to plan the next one. Because once you fall in love with road trips, there’s no going back.

Bonus: Apps That Will Save Your Road TripRoadtrippers—

  • Roadtrippers – Build your route and find cool stops along the way.
  • GasBuddy—Locate the cheapest gas nearby.iExit—
  • it – See what’s coming up at each highway exit.
  • Waze/Google Maps—Avoid traffic and detours.
  • Spotify/ApplePodcasts—sYour best road buddies
About the author

Gabriel Gonçalves