FOR THE PAST DECADE and a half, Rob Machado has surfed the planet. In the 1990s he was a top competitor on surfing's pro tour, lauded for blending a soulful style with aerial acrobatics. Today he's the most sought-after free surfer, riding far-flung breaks for films and photo shoots. (He still competes on occasion, winning Oahu's Pipeline Pro in February.) And while he's lost track of all the breaks he's visited, his Zenlike approach to wave hunting is as legendary as his Afro. Mark Anders recently quizzed "the Mob" about the chemistry of a good trip.

On the pro tour, you surfed the world's top breaks all the time. Why did you bail?
The tour dictated my whole year—I always knew where I had to be. In February, it was Australia; then Tahiti, then Fiji. I started feeling like I was in Groundhog Day. My first trip after I retired was to New Zealand. It felt so good to go with a tight little crew and surf a wave we'd heard about for the last ten years.

What's the biggest challenge of surf travel?
Surfboards. They're always a pain. I used to have these big bags carrying eight boards, plus wetsuits and towels. I've learned to keep them light, because if you start loading too much gear inside, the baggage guys get pissed and throw it around. I also put bubble wrap between the boards. Then just cross your fingers.

How do you deal with locals who might not want to share their break?
Usually people in remote areas are really excited for you to be there. But it's their surf spot and maybe they don't ever get to leave, so you have to be respectful. That can mean not surfing. I was staying in Beqa, Fiji, in this village. It was Sunday, and you can't do anything there on Sundays. So I just posted up under a tree with some locals; 14 bowls of kava later, I crawled back to my room.

All the travel and exertion makes it tough to stay healthy. What's your trick?
Stay on top of all your cuts. You'll get reef cuts and won't even realize it, then you wake up the next day and they're all red and swollen. Pack Band-Aids and Tea Tree Oil and take care of yourself.

Name one big surf trip you dream about.
Chile. I saw a sliver of it when I went there in 2004. The coastline is equivalent to Cabo San Lucas up to Alaska, and there are waves all over. It's out of control.