Imagine what it might be like to skateboard on water, performing tricks as a boat pulls you forward. That’s somewhat like wakeskating, an offshoot of wakeboarding where riders don’t strap their feet to the board. Now imagine doing that in ponds, rivers, canals, swimming pools, and even fountains, and you’ll have an idea what Brian Grubb does for fun.

Grubb is one of the world’s best wakeskaters, with five Wakestock pro wakeskating titles under his belt at the age of 32. After learning to wakeboard when he was 12, he fell in love with wakeskating because it combines elements of his other favorite activities, including surfing, snowboarding, skydiving, and bungee jumping, which requires good body control. The sport also leaves room for creativity, both in terms of tricks and terrain. Once Grubb decided to wakeskate on the canal in front of Canada’s parliament building, getting up early in the morning so security guards wouldn’t catch him as he launched himself over a 12-foot drop gap. Another time, on his 30th birthday, he went to skate in Las Vegas fountains, performing tricks as he rode behind a winch, or a machine that pulls wakeskaters on surfaces too enclosed or isolated for boats and jet skis.

Grubb was formerly named wakeskater of the year by Wakeboarding Magazine, now TransWorld Wakeboarding magazine, and today he has racked up 22 tour wins and four overall series championships on the Wakeskate Tour, a series of competitions that puts him up against the world’s other top wakeskaters. He has dabbled in film as well, taking home another award for his wakeskating role in the movie Out of the Pond, by surfwear company Billabong. These days, Grubb is also working with Vertigo Bungee to launch a commercial bungee jumping business in Kentucky, on what he says will be the highest bridge for commercial jumps in the United States.

Here, he tells us about dodging saltwater crocodiles in Australia, his first time on a wakeboard, and his ambition to free fall from outer space.

Describe your perfect day, from dawn 'til dusk. Where would you be, who would you meet, and what would you do?
My perfect day would take place somewhere on an island in the South Pacific, like one of the French Polynesian islands around Tahiti with a left and a right point break. I would wake up, eat some mango and pineapple for breakfast and then go surf for a few hours. After lunch I'd go for a skydive or two with some beach landings. During the last few hours of daylight I’d do some wakeskating with friends and then have a few beers while watching the sun set with my girl.

If you could travel somewhere you've never been, where would you go and why?
I’d go on a surf boat trip around the Maldives islands, south of India in the Indian Ocean. It would be so fun to stay on the boat and explore different waves for a couple weeks with small crowds, or no crowds. It would be ideal to have a PWC [personal water craft] onboard so we could wakeskate, too. I've seen pictures of the Maldives in surf magazines, and a friend who went on a surf trip there a few years ago said it was amazing. I’ve heard the islands are in danger of going under if ocean levels rise, so it would be cool to go now.

Where is the best place you've ever visited? What made it so special?
The Kimberley region in northwest Australia, where I went on a Red Bull trip called Northern Tides a few years ago. It's one of the most remote places on earth and has some of the largest tide changes in the world, at over 30 feet. The rest of the Red Bull wake team and I explored the area on a boat for 10 days, and we only saw one other boat the whole time.

It was one of the most amazing places I've ever ridden even though we were constantly trying to avoid the saltwater crocs. A guy on a PWC followed us when we rode so we could hop on the sled when we fell instead of sitting in the water. We only saw five or six crocs the entire trip, but it was still unnerving to see one slide down the muddy bank into the water as I was getting ready to ride on the back of the boat.