It’s Labor Day Weekend here in the U.S., and many are getting in the last road trip of the summer.

When I was a kid, a road trip involved a Rand McNally Road Atlas, a highlighter and weather intel from the gas station attendant. “Yep, looks like rain.”

But in 2024, we have hi-tech options that help us find the best routes, weather, sites, food and much more.

Travel Weather Planner: Wayther

If your road trip involves more than one region, it can be tough to track weather patterns. A new iOS app released this July does it for you. Wayther (clever name!) helps you take environmental factors into consideration as you travel. It’s not out for Android yet, but Apple folks can create three trips for free.

The Ultimate Road Trip Tool: Roadtrippers

I’ve written before about my love of the Roadtrippers app/site. And, of course, they’ve jumped on the AI train with their new tool, Autopilot.

You have to have a Premium version of Roadtrippers to use the new feature, but it may be worth it. The tool asks a series of questions to find out when you’re traveling, where you’re going, with whom you’re tripping and in what (car or RV). Then it applies AI to the database of kabillions of other trips to plan out the perfect road trip.

You can still use Roadtrippers for free to manually plan your dream trip, but paying no more than $5 a month for the extra features may be worth it.

Best Trip Organizer: TripIt

Maybe it’s just because I’m a road warrior, but TripIt is one of those apps that I would be lost without.

I’ve had it for y.e.a.r.s. It’s a simple interface (web and app), and it makes my life so much easier on the road. I just forward travel confirmations to plans@tripit.com, and they’re automatically organized into individual trips with all the pertinent info organized into individual cards I can flip through on the go.

Everything I need is at my fingertips, online and off. And because I pay the fifty bucks a year for TripIt Pro, I get notifications when the price of my flight decreases. Each and every year I’ve been able to get credits for the differences, and that means each and every year TripIt Pro pays for itself.

There are plenty of other benefits to the pro, but if you’re just trying to wrangle all your confirmation emails, the free version might be just fine.

Other AI-Based Travel Help

ChatGPT and all its AI cousins (Google Gemini, Microsoft Copilot, Meta.ai, etc.) have all gotten into the trip-planning game. Go to any of them and ask for vacation ideas, itineraries, local hidden gems or anything else travel-related. In addition, major travel sites are developing their own tools. Try Expedia’s new Romie virtual AI concierge.

Another AI planner is fast and fun. Layla.ai is delightful to chat with. I am spending time with the family in Lafayette, LA, this Saturday, and Layla suggested all kinds of ideas I had never even heard of — and I used to live there.

Before we leave the AI-powered trip planner world, check out this article from the New York Times. It rounds up multiple tools and functionalities.

Pit-Stop Help: iExit

Finally, let me give another shout out to the best bathroom finder for the road. I love iExit, the app that helps you find restaurants, gas and other road trip necessities while you’re traveling down life’s highways. Sometimes I have to drive 3-4 hours to a gig, and I use iExit to plan where to stop for provisions rather than waiting until I happen to glimpse a road sign on the way.