THE SAILING SURFER
Two-time world champ and Olympian surfer John John Florence is a Hawaiian waterman who has discovered one more thing he loves about the ocean: catching the wind in his sails.
When a two-time world champion surfer isn’t riding the breaks in his native Hawaii, chances are good you’ll find him tearing between islands on his Gunboat catamaran.
Oftentimes referred to as “The Seven Mile Miracle,” the North Shore of Oahu, Hawaii, is a rugged stretch of coastline that has become more historically significant in the surfing world than any other place on the planet. With reef breaks and deepwater bays that pick up the big north swells of passing winter storms—combined with a deeply ingrained Hawaiian surfing culture—the North Shore has become a mecca for the sport. Naturally, the North Shore has produced some incredible surfing talent over the years. When the trade winds build and the waves go flat in the summertime, however, some of the future kings and queens of surfing inevitably find themselves bored and looking for other ways to score cheap thrills out on the water.
One of them is the North Shore’s own John John Florence, who just this past summer represented the United States in the first-ever surfing competition at Tokyo’s Olympic Games.
“My friend Erik had a Hobie monohull, like 12 feet long or something, and one day, three of us sailed it to Waimea Bay and back,” Florence tells me. “That was my first sail, but I was hooked. I knew
immediately that I wanted a boat like that, so I got a Laser 2. I would lie in bed at night watching Volvo Ocean Race videos on Youtube. And then we would go out on the Laser 2 and pretend we were doing that kind of stuff. We would go out and sail as fast as we could because there was so much wind. Just ripping.”
At the time, however, Florence wasn’t just some random North Shore grom with a surfing and sailing habit to support; he was the boy who would become king. Growing up with Hawaii’s most famous wave—pipeline—right in his backyard, Florence and his brothers, Nathan and Ivan, were groomed to ride the North Shore waves like nobody’s business. The youngest surfer to ever compete in the prestigious Vans Triple Crown of Surfing at just 13 years of age, John John Florence was long destined for greatness. It wasn’t a matter of if but when. Florence was the North Shore’s chosen son, the greatest hope for a Hawaiian to reclaim the world surfing title since the late, great Andy Irons. But in the offseason, this future surfing world champion continued to explore his passion for sailing.
“From the Laser 2, I always just wanted to go faster and faster, so I got a Hobie 16, and that was a huge learning curve for me. I was always really attracted to the idea of multihulls because of their speed. Again, being in Hawaii, there’s a lot of wind and swell, so the learning curve is pretty steep. After the Hobie, I got a racer/cruiser, a J/35. And that was the first time where I felt like: Oh, now I can go to different islands. Now I can go to these places that you can get
to only by boat sometimes. So that was a game-changer. There’s just a really special feeling when you are out there and doing it yourself and by your own means.”
As every cruising sailor knows, “it’s very rewarding,” Florence says.
From Gun to Gunboat
Roughly 10 years later, that same young man who was going full-send mode on a Laser 2 and a Hobie 16 is now a two-time world champion of surfing who still wants to go fast on sailboats during his time off.
When not surfing for a living, there’s a pretty good chance Florence is still doing it for pleasure. A boat that could cover big distances very quickly and take him to world-class waves would be the ticket, which brings up the million-dollar question: If you’re a rich, young and famous world-champion surfer who wants a fun, fast, sexy cruising boat, what do you buy?
The answer: a Gunboat. A Gunboat catamaran is exactly what you buy. In essence, he was adding a Gunboat to his “guns,” surfer shorthand for maneuverable short boards.
“When [professional snowboarder] Travis Rice called me and said that his Gunboat was for sale, I just thought, Oh
my gosh this is a really cool opportunity. And I got really excited. It’s such a unique boat, and there’s just nothing else like it. I had been on the boat a couple of years ago in Tahiti and gone for a sail on it, and I had always said that if I got a bigger boat, I wanted something exactly like Travis’ Gunboat. So when Travis called me and said he wanted to do a Line Islands trip up from Tahiti to Hawaii and then pass the torch, I was definitely interested. The timing was right, and so it worked out.”
At that point in John’s life (he was 25 years old at the time, some three years ago), he had just won his second consecutive world championship title. His new-to-him Gunboat 48 had just sailed in from the South Seas, and he was raring to give it a go. With legendary French offshore multihull ace Jacques Vincent acting as Florence’s coach and mentor, he took his first interisland trip to surf what was forecast to be one of the biggest swells of the winter. Florence, a past winner of the legendary Eddie Aikau Big Wave contest at Waimea Bay, wanted to surf the iconic big-wave break on Maui known as “Jaws.” The swell didn’t quite live up to the hype, but after his first interisland voyage on his new Gunboat—now named Vela—he was stoked on the boat and his newfound experience.
“I called Jacques as soon as I got the boat,” Florence says. “He’s done pretty much everything and has sailed all of
the big multihulls, so someone like him on board is cool because he knows what to do in every situation. He’s very calm all the time, even when something goes wrong or the spinnaker gets wrapped. I’ve learned so much from having him on board, but mostly to stay calm even when stuff breaks or goes wrong. The boat is such a cool boat because it’s relatively simple, and I feel like I can understand the systems pretty easily. It’s also a fast boat, and having the lighter weight and good hull design makes it super fun to sail. Especially when you have the spinnaker up here in Hawaii, you can get up over 20 knots pretty quickly. To be on a big boat going that fast—carrying all your surfboards—is just insane.”
Bound for Blue Water
Crazy as it might be, traveling across the ocean at high speed with your surfboards and friends is a dream shared by many sailors and surfers the world over, including this writer. Florence says: “To be able to cover big distances as quickly as possible, to get to remote surf breaks on your own boat and by your own means… that’s the goal. To combine the two, surfing and sailing, is what I want to do.”
With a boat capable of covering miles in wholesale fashion, and an adventurous spirit that constantly keeps him on an upward trajectory as a sailor, Florence began looking toward a bigger journey on board Vela.
Located just 1,000 nautical miles south of Hawaii, the islands of the Northern Line Islands archipelago are the closest inhabited pieces of land to the Aloha State and served as a logical destination for Florence’s first bluewater cruise on
Vela. Roughly halfway to Tahiti, the group consists mainly of Palmyra Atoll and a handful of other atolls that belong to the nation of Kiribati. While Palmyra is administered by the US government as a nature preserve, one can legally visit the atoll so long as they have acquired the right permits and taken proper precautions before leaving Hawaii. Renowned for its wildlife and thriving ecosystem, the atoll is a gem of the central Pacific that is as unspoiled as they come, despite being used as a dumping spot for unexploded munitions and a strategic military base during World War II.
Once again taking French sailing ace Vincent as crew—plus filmmaker and friend Erik Knutson, brother Nathan and friend Kona Johnson—the crew of five was able to raise the low-lying atoll out of the deep blue Pacific after just a few days of sailing from Honolulu. On a voyage that consisted of everything from reinforced stormy squalls and periods of complete calm to idyllic reaching across perfect trade-wind conditions, the Gunboat continued to prove its chops on the open ocean. “All of a sudden, we were close to Palmyra and the circle of life that’s living down there. I really wanted to learn about it and experience it. There are these birds and fish and coral reefs down there that are thriving. It was incredible; I’ve never seen anything like it in my life,” Florence says.
After a few days of touring Palmyra with scientists from the Nature Conservancy, Vela weighed anchor and traveled farther down the Northern Line Islands chain to the atoll of Washington Island, part of the nation of Kiribati. “It’s an interesting contrast to show up to somewhere like Washington, where you’ve never been before, and you don’t know anyone from there…these people had no idea that we were coming. They’re just in the middle of nowhere, kind of out there by themselves. You all of a sudden
have this sense of exploration that you feel like people probably had hundreds of years ago,” Florence says.
A unique atoll that has the largest freshwater lake of any atoll on Earth and no navigable reef pass, it provided Vela anchorage outside the reef in favorable surfing conditions. An A-frame wave broke both left and right, so the boys spent some time surfing and exploring the outer reefs before moving on to the larger and more-populated Fanning Island.
After a quick passage to Fanning, Vela anchored just inside the pass before meeting with the locals—many sailing traditional outrigger canoes—and exploring the island. Just outside the channel lies a renowned left-hand-breaking wave that is the stuff of legend to those in the know. Unlike the waves in Hawaii and other more-populated surfing destinations, the crowd at a place such as Fanning Island is simply nonexistent. The crew of Vela did, however, encounter one young local surfer during their stay. Imagine being a youngster on Fanning and surfing your home wave on an old hand-me-down board that some foreigner had left, only to have a two-time world-champion surfer and his friends rock up and share a fun-filled session with you. It’s equally the stuff of legend and the kind of experience that can transcend language and culture in a way that only sport, friendship and camaraderie can. Such exchanges are oftentimes what cruising is all about.
“I’ve done a lot of sailing trips with Kona and Erik and my brother. For us to all be that far from home, in the middle of nowhere, it’s a surreal feeling. I think I’ll continue searching for that feeling for the rest of my life,” Florence says, regarding this first offshore cruising mission on his new catamaran. Needless to say, it sounds as though Florence is hooked on the cruising lifestyle—and his maiden bluewater voyage on Vela certainly won’t be his last.
Stoked on Sailing
It’s safe to say, though, that Florence isn’t hooked on cruising alone; he is stoked about every aspect of sailing. As a young man who has dedicated his very existence to pushing the performance envelope in his given sport, it’s only natural that Florence would find himself deeply drawn to the foiling revolution that is currently taking place in both sailing and surfing. Which is why he’s added another catamaran to his quiver: Flying Phantom, an 18-foot foiling cat. Whether foiling on a surfboard or on Flying Phantom, Florence is constantly trying to take his game to the next level.
When flying around Kaneohe Bay, Oahu, at more than 20 knots wasn’t adventurous enough and he had additional time at home due to the pandemic, Florence teamed up with famed Maui waterman and foiling guru Kai Lenny to sail the 18-foot foiler across Hawaii’s longest channel. Kauai Channel is a run of about 100 miles in a straight line, and Florence and Lenny zipped across it from Oahu’s windward side to Kauai’s Hanalei Bay. A few days later, the duo sailed back to Oahu, again finding some epic foiling conditions in between. It’s not quite your conventional “cruising” boat or adventure, but it’s sailing, which Florence has come to love.
With lightning-quick reflexes, supreme athletic abilities, celebrity status, and a constant desire to push and progress, Florence has found himself in a unique position to continue landing berths on awesome boats. One of these unique opportunities that presented itself—and a sign of his meteoric rise in the sailing world—was getting invited on board top-tier Australian racing yacht Winning
Appliances, and then sailing it to a fourthplace overall finish in the 2018 Sydney to Hobart race. Just days later, Florence was hitting ultrahigh speeds just above Sydney Harbour with the likes of Aussie America’s Cup veteran Tom Slingsby and the Australian Sail GP crew on training sessions on a foiling F50 catamaran.
“I think for me in the future, I have some big thoughts and dreams about doing some big trips on the Gunboat,” Florence tells me. As an avid surfer and sailor, it seems he’s already found the ideal platform to combine his two passions. With an open ocean that seemingly has no end, it’s almost a certainty that Florence and Vela will continue exploring new places to sail and new waves to surf. Unless your name is Kelly Slater, surfing at a championship-tour level has a rather limited shelf life. With Florence’s penchant for constant progression and the thrill of competition constantly enticing him to reach new heights, it seems inevitablea that Gunboat voyaging is only the tip of the iceberg in his sailing career.
“I’m very inspired by the Vendée Globe competitors and the guys sailing the giant foiling offshore trimarans. Those boats are just crazy. That’s another thing I love about sailing: the design and the constant innovation. Like, how can we be faster in the open ocean?” he asks rhetorically.
“I don’t know where I see myself on the racing side of it, but I would definitely love to be a part of some races in the next few years. My experience in the Hobart was invaluable. I love learning and gaining those experiences and getting inspired and being excited.” World-champion athlete or not, isn’t learning and getting inspired and excited the whole point of sailing and cruising? I don’t know where sailing will take Florence in the years to come, but I can’t wait to find out, and I’ll be rooting for him the whole way. Aloha, John John, and best of luck.
After several years roaming the Pacific himself, sailor, surfer and CW contributing editor Ronnie Simpson is once again based in Hawaii.