Annual leave (or PTO to our American friends) is precious and it can be hard to know exactly how you want to spend it. Do you want the chaotic energy of a big city, an itinerary packed with day trips, or downtime at the beach? We've all been there: Googling...

Note: This post was originally written for a trip I took in 2024. In 2026, I'm planning another trip to Thailand, and have updated this post with the process as it is today. The overnight sleeper train from Bangkok to Chiang Mai is pretty much a rite of passage for...