A Sailor Plans an Arctic Expedition Via SUP

“After I did the Race to Alaska, people would often throw that word at me,” says Kruger. “They’d say, ‘Did you always know that you’d be doing extreme stuff like this?’ It took me a long time to find the words to explain why that pissed me off so much.”

Extreme or not, this sailor and consummate waterman of Orcas Island, Washington, is at the apex of the SUP world. Kruger drew international interest in 2017 when he was the first, and to date the only, person to complete the entire Race to Alaska, or R2AK, on a standup paddleboard. For the uninitiated, the competition is a 750-mile race from Port Townsend, Washington, to Ketchikan, Alaska, primarily through British Columbia’s Inside Passage. The only rules are no engines, no privately arranged support and two mandatory waypoints.

Simply completing the R2AK is an epic accomplishment for skippers of some hotshot racing sailboats, as roughly a third of the teams flunk out due to a myriad of factors, including log strikes, busted rigs and shot nerves. To attempt to do it in a SUP is like taking a pogo stick up Mount Rainier. But Kruger completed the race, and he placed 17th out of 27 teams.

Kruger feels his long-distance paddling is a form of communion with with nature. He doesn’t understand why what should be seen as a return to normal is instead viewed as radical. And he doesn’t want to be perceived as an Olympian on a pedestal. Instead, he hopes others will reestablish their relationship with nature and recognize their own latent power.

“For the R2AK, I just went out with a carbon fiber sled, good training and a GPS. There is nothing extreme about that. It was just dipping into a little corner of my humanity.”

To run the race well, preparation was key, as was a mastery of flow state. “I talk about flow state a lot,” says Kruger. “Paddling is based on breath. It’s yoga. It’s meditation. It’s qigong and tai chi. It’s what all those traditions and disciplines are trying to get at. I can think back and tell you something about every mile of that paddle. It was like this dual state of being switched on—you’re not missing anything and you’re everywhere at once. You’re a radio tower for information. The floodgates are open, and it just comes pouring in. So much data. It’s amazing.”.

These days, Kruger is almost inseparable from his sailboat and home, Raven, a Bruce Roberts design built in Havre de Grace, Maryland. He acquired the 68-footer shortly after his historic R2AK paddle. He has interesting plans for her, but for now, he is hosting artist-in-residence programs aboard the steel boat with the help of his fiancé Elyn Oliver. I joined the couple aboard Raven recently, to catch up with the Kruger and learn more about what he’s been up to since his historic paddle.

As it turns out, just five years after the R2AK, he set his sights even farther north. In 2022, he began his Arctic Project, a multiseason, unsupported, 1,900-mile Northwest Passage SUP expedition “I’ve done two seasons up there,” says Kruger, who paddled 420 miles in the summer of 2022, making it from Tuktoyatuk in the Northwest territories of Canada to Paulatuk. Weeks passed during which he never encountered a single person. Kruger returned to the Arctic in the summer of 2023 for the next leg. He put in at Paulatuk and ended in Kugluktuk in Nunavut, Canada. logging 487 miles.

When Kruger describes those Arctic summers, he sounds like he experienced a sort of spiritual rebirth. The competitive, stopwatch-driven athlete motivated by winning events underwent a dramatic change. The realization struck him within the first 300 miles.

“Post R2AK, I got up there and I realized that the only thing that mattered to me was learning about the place,” explains Kruger. “I didn’t want to go fast. I wanted to slow down. I wanted to spend more time. I wanted to dive into the place and sink my teeth into it.”

In addition, a surprising reaction swept over him. “Then came the shame of going up there, gunning after a title,” says Kruger. “There’s no honor in going into someone’s backyard claiming to be the first to do something. When you go up there you see all the signs of all the people who have lived there for millennia. The old camps. The tools. Obviously, the people who still live there. You hit the beach up in the Arctic and it’s all bones,” he adds with reverence.

The epiphanies he experienced during those Arctic summers prompted him to think about his future aboard Raven.

“One of the things I’ve always wanted to do is a Figure 8,” he says. That’s a sailing route that combines an around the Americas loop—to include the Northwest Passage and Cape Horn—with an Antarctica circumnavigation. The route is synonymous with modern solo sailing legend Randall Reeves. The San Francisco native and former restaurant industry professional first did the route in 2018 with the 43-foot aluminum double-headsail sloop Moli. “I’ve got a boat that can do it, so I feel like it should be fun,” says Kruger.

There is some urgency to his mission. “Everywhere I go people want to talk about their changing relationship with where they live. With this Figure 8 project, I want to tell the stories of the sixth-generation trolling family out of Craig, Alaska,” he says. “I want to talk about the young guy that I met in Paulatuk who is learning how to spear hunt seals instead of going out with a rifle. I want to tell the stories about the fish that are showing up in the Arctic that have never been seen there before.”

Kruger’s goal is to fill the boat with creatives who can help him distill these experiences and put their stories out there. “Then we’ll be reaching that many more people,” he says. “At the very least, we can touch ‘em in the feels. I think a lot of people have forgotten the fact that we live on Earth.” He invokes Cousteau, recalling the effect that those adventures and programs had on his childhood. “That work was needed then, but it’s needed even more now.”

To make the Figure 8 happen, Kruger will need to get a couple of big pieces into place, including financial support. He’s working on a few of the pieces now, which is why he had to abandon the Arctic Project in summer 2024. But he plans to return in 2025 to run another 1,000 miles to Pond Inlet. This time, though, he’ll do it a different way. He’ll deploy a 24-foot freighter canoe with support crew.

“I’ve been alone and unsupported for 900 miles. For the final 1,000, I’m using an Inuit freighter canoe, a design that’s been in use up there for 100 years.” The final 1,000 miles could be the most challenging for this SUP adventurer. “Some of the crossings are weighing on my mind,” he says. “Doing them alone may not be the way to go, for a lot of reasons, including the availability of water, the serious nature of the crossings, the amount of ice and of course the large mammals.”

He’s in the off-season now, but he continues to prepare for next summer. There are physical training sessions with Chuck Silva, an Orcas Island mixed martial artist. Kruger’s prep also includes time spent monitoring weather. “I’m storm watching all winter long,” he says. “Every one of these blows that comes through I’m out in it.” The foul-weather paddles provide excellent cardio, strength and balance training.

But the winter of 2025 is not just for Arctic paddle preparation. Kruger recently launched artist-in-residence weekends aboard Raven, which could provide insight for the Figure 8 Project.

During my visit with Kruger and Oliver, a local painter and surfer poet were aboard for a weekend in the San Juan Islands. The couple had picked up their charter guests at the Orcas Island Ferry Landing and then run to the west end of Harney Channel before dipping through Pole Pass and into Deer Harbor. After a transit through Spring Pass, the anchor was dropped in Reid Harbor at Stuart Island, where they spent a few hours walking the winding trails and gravel roads.

Kruger and Oliver’s charter skills are evident in the charcuterie boards, cocktails and Kruger-hunted venison stew they serve. Talks about good books and artistic processes go late into the night. The next morning, they run to Gossip Island—an idyllic islet that looks like a manicured Japanese garden with trim moss carpeting and windswept trees with twisted trunks. From there, the sail to the night’s anchorage at Jones Island is spirited as a consistent 20- to 25-knot east-southeast breeze kicks Raven right along. Kruger diligently handles the trim through 30-knot gusts. Raven is a rock, offering a secure and smooth ride throughout. Her destiny is ice fields, not regattas.

The anchor is dropped at Jones Island and the crew heads out for a trail hike among the bright red trunks of Madrone trees and lichen beds. Kruger enthusiastically caws at the ravens encountered. The night sets in. A polar plunge with the painter and poet is in order.

That night, sitting in Raven’s warmly lit salon with Kruger, there are so many questions and concerns about the Arctic trial and Figure 8 Project that we could talk through. But our minds are clear and we’re all relaxed. I recall what Kruger said about his endeavors, and how they are not extreme but more like a return to our roots. Dip the paddle and have a real chat with a stranger. Take a painter and a poet sailing. Freeze in and just be. That doesn’t seem so extreme to me. 

January 2025