Driving across the United States is an aspirational trip for many people, but also a daunting one: How do you plan it? What route do you take?

This was the challenge I faced when my partner, Cliff, and I decided to drive from our home in New York City to Los Angeles, where two of our children live. Our priorities were to hit some states we’d never visited and craft an itinerary that included our favorite things: vintage diners, Frank Lloyd Wright homes, automotive landmarks (for him) and factory tours (for me).

We started by picking a few intriguing waypoints and building the trip around them. One was Polymath Park, a collection of Frank Lloyd Wright homes in Pennsylvania where you can stay overnight; another was the “Field of Dreams” movie site in Dyersville, Iowa; and a third was an Airbnb rental made out of a refurbished grain silo in Lava Hot Springs, Idaho.

To connect the dots, we used an assortment of apps and websites that helped us plan a master route and improvise along the way, finding hotels, restaurants and weird attractions. Cliff drove, and I rode shotgun as navigator, wielding the apps. We wound up driving cross-country and back: 8,300 miles over 28 days, through 24 states. The tools below are the main ones we used.

Itinerary Planning

Roadtrippers

Roadtrippers was the scaffolding of our trip, and I found it as addictive as it was helpful. It lets you plan an itinerary on a virtual map from point A to point B — in my case, drawing a line from New York to Los Angeles and filling it in — and suggests everything you’ll need along the way. For instance, as we were making our way west from Mount Rushmore, the app surfaced nearby attractions, prompting us to make a detour to “Carhenge” in Nebraska (a Stonehenge replica made of junked cars) and the Durham Bison Ranch in Wyoming, where we got up close and personal with the beasts.