I stopped asking myself where I want to go a long time ago. Instead I ask who I want to be with. Every departure from Maui, thousands of miles of ocean between us and everyone we love, has to be justified by what is waiting on the other side. This is the most practical travel advice I can offer.

Every May, without looking for it, the NYT 100 Best Restaurants list finds me. And the thrill lasts about thirty seconds. Then I get to work. Here is the exact system I use to turn a great list into a living tool, and how you can do the same for any city you are planning to spend real time in this summer.

After years of overstacking our summers, too many cities, too much driving, arriving back on Maui hollowed out instead of restored, I stopped building itineraries and started building beats. One city. One purpose. One note in a greater song. Here's how I actually do it, and the simple tools that make it work.

I start every summer trip the same way. With the last flight. The return home. Once that's locked in, dates, destinations, decisions are easier to define. It might sound counterintuitive, but booking the end first is the most practical move I know. Here's why it works, and the tools I'm using to do it smarter than ever.