How to Roadtrip
Last updated February 12, 2025.
This is brief write-up of some of road trip tips.
Packing
Pack light. Or at least lighter than you think. No one’s going to see you for more than 20 minutes at a time. They’re not going to know that you wore the same snazzy t-shirt and sweatpants combo yesterday. And if you’re driving across the US, chances are your outfit is the fanciest thing they’ve seen all week. The less you pack, the less you’ll schlep into your hotel every night.
Pack modularly. If you need to pack for different climates, different occasions, or different activities, pack the different stuff in different bags. In 2022, Wiff and I drove from NYC to San Diego to watch my brother make Chief in the Navy. We packed roadtrip clothes in one bag, and Naval ceremony clothes in the other. That way I didn’t have to carry a suit and tie into every dumpy hotel we stayed in along the way.
Driving
Pick your long poles. Pick a few must-see spots and plan around them. In the above trip, our long pole location was San Diego, but we didn’t care where we stopped along the way. Knowing we were always going the right direction gave us the flexibility to be spontaneous.
Set a drive time limit. Over the years our roadtrips have evolved. In the early days, we’d drive 18 hours to make it from Tacoma to Irvine or 12 hours to from NYC to Chicago in a day. But those long drives can get tedious. It’s no fun pulling into a big city and not wanting to go grab a drink because you want to blow your brains out. On our last few trips, we’ve set a daily limit of 4-6 hours. This is partially because we' have an old dog and endless hours in the car can be hard on her, and partially because we’ve wanted to see more of the towns we stop in.
Dining
Early on, when we wanted lunch on the road, we’d hit up whatever fast food joint was just off the highway. It was convenient, but the daly routine of Taco Bell, Applebee’s, and catastrophic diarrhea got tedious. Now, we’ll grab a salad and half sandwich at Panera or stop at a grocery store and make our own salad. The Paneras and grocery stores tend to be a few miles off the highway, which initially annoyed me, but now the 10 minute drive off the highway is a welcome change of pace.
On longer trips, we’ll bring our Yeti cooler for snacks wine and it’s amazing.
Apps
Route planning: We’re Apple Maps people and have never had an issue. It’s ETAs have always been accurate, and the directions almost always align with Waze and Google Maps, which we’ve tested a few times over the years.
Music: Apple Music and Spotify.
