Issue #164: My Ultimate Guide to Planning (and Enjoying) Any Trip

Plus highlights from Osaka and Kyoto.

As many of you already know, in mid-August I departed for a six-week trip that took me from Indonesia to Japan and South Korea. What I haven’t shared is that I almost called the entire thing off. During a layover in the Jakarta airport, en route from Lombok to Tokyo, I sat in a quiet spot a few gates away from my own and looked over some of the train routes I would have to take in Japan. As I did, I felt almost crushed by a sense of overwhelm—how was I supposed to get from the hotel to my Airbnb, much less Kyoto to a small hot spring town? The gate I was sitting in went to SFO, and I briefly considered switching my flight. I even texted a friend, “I’m thinking of coming home?” Ultimately, it was my careful planning that buoyed me enough to board the flight to Tokyo and—it’s no secret—I’m so glad I did. Read on for my tips for planning any vacation, including where to start, the Google Doc template I use for every trip, and some inspiration for your next big adventure: