Roy was a little over a year old when his parents went to Alola (where they appear in the Gen 7 games.) It was his first big vacation ever, as any previous trips had been just around Kanto or to Johto at the farthest. While Roy was a pretty easy going baby, travelling on a long trip with him was a new experience for Red and Green. He got pretty bad jet-lag that resulted in a few sleepless nights, but luckily was able to adjust to the different time zone before too long.

Alola was Roy’s first experience being somewhere completely different from his home and he was entranced by all the colorful sights and sounds, seeing new pokémon and getting to spend lots of time at the beach. Red and Green definitely noticed how much Roy loved Alola, and considering they also had a great time there, they decided to try and visit there semi-regularly on family trips (as well as places like Kalos, which is where Red and Green got engaged!) This ended up sparking a love of travel in Roy, prompting him to want to start his journey somewhere other than Kanto. So, after brainstorming with his step-cousin Jay, the two decide to start their journey in Galar, since the League there seems so exciting and different from Kanto’s. 

Eventually after two years traveling with Jay in Galar and then Kalos, Roy and his cousin part ways, with Jay heading back to Kanto to focus on his research and Roy heading to Sinnoh to keep practicing his skills as a trainer. It’s in Sinnoh that Roy meets Draco and then Ulyssa and starts traveling with them, and also meets some new rivals in Emery, Gavin, and Renato’s group! 

Send me a  🖊 and a character and I’ll write out some headcanons for them!