Sailing for the [Dog]Smiles

Nonprofit founder and crew compete in 750-mile engineless boat race to Alaska

By Christian Weaner

Shortly after Jon Totten moved back to North Idaho in the spring of 2020, while he and his friend Gabe Mills were sailing on Lake Pend Oreille under the full moon one evening, Gabe asked Jon if he had ever heard of the Race to Alaska (R2AK), a 750-mile engineless boat race considered something like the Iditarod on a sailboat. "And I was like, 'Oh yeah, man, I'm a big fan,'" Jon recalled. "[Gabe asked], 'Would you ever want to do that?'"

"And I was like, 'Are you kidding? I'll go tomorrow. I'm in.'"

This past June, nearly three years later, Jon, Gabe and fellow crewmates Jay Taft and David Kilmer finally embarked on the marathon boat race, representing Team Dogsmile Adventures in the 2023 R2AK.

Despite challenges along the way and an unexpected finish, Jon and his team learned some lessons, made meaningful memories together and spread the word about Jon's nonprofit sailing business, Dogsmile Adventures.

Jon grew up on a farm in Wisconsin before moving to Idaho when he was 18 to attend the University of Idaho. After graduating, Jon moved to Coeur d'Alene, where he took a job at North Idaho College, shortly thereafter learning to sail for the first time.

Jon quickly developed a passion for sailing, which eventually led him to a full-time career working on boats, first on the Pacific Coast and later in the Caribbean. He spent five years as a sailing instructor and starter captain, living primarily on the island of Grenada. The work was good, but it wore on Jon over time. In 2019, feeling burned out and ready to give up, Jon made the decision to check into a drug and alcohol rehabilitation center and get sober.

"I decided to find a new direction in life at that point," Jon recalled. "I wasn't going to go back to work in the Caribbean, but I had a sailboat that I had purchased—the boat's name is 'Dogsmile'—and it was down there, and so I had to figure out what to do with it. That's what led me on this whole journey to what I'm doing now."

Jon had initially planned to bring his boat back to the U.S. to try and sell it in March 2020, but when the pandemic began his plans fell through. Ultimately, he decided to keep the boat and bring it back to North Idaho, embarking on a three-month journey of a lifetime.

"I traveled 24,000 miles by land, air and sea in the spring of 2020 while most people I knew were locked in their homes," Jon recounted. "I brought the boat up here and then launched a nonprofit."

Dogsmile Adventures is named for the light-hearted, toothy grin that Jon's childhood dog used to exhibit, and the organization's mission is to "create powerful opportunities for people to discover healing and potential through sailing adventures.”

When Gabe approached Jon about participating in the R2AK shortly after he had moved back to North Idaho, Jon saw it as an opportunity to not only compete in the world-class boating competition he had always dreamed of but also as an opportunity to share the Dogsmile story with a wider audience. So, Team Dogsmile Adventures was born.

Because of the pandemic, the 2021 R2AK was modified to become the Washington 360, a shortened 360-mile version of the engineless boat race that ventured through the Puget Sound. Although Jon, Gabe and their fellow crewmates were bummed not to go to Alaska, they made the most of the WA360 and realized just how competitive they all could be, finishing third place out of 65 boats.

Equipped with the skills and experience from the WA360, the Team Dogsmile crew spent the next two years training and entered the 2023 R2AK confident in their ability to compete.

Team Dogsmile finished the first leg of the R2AK—a short 40-mile jaunt from Port Townsend, Washington, up to Victoria, British Columbia—in under six hours. Beginning the much longer second leg of the trip, which stretches 710 miles from Victoria to Ketchikan, Alaska, the team felt prepared and ready to go.

But Jon, Gabe, Jay and David quickly realized that the further north they went, fewer boats surrounded them, all cell phone reception was lost, and the race became increasingly treacherous. "Once you get out there a way, it just gets wilder," Jon described. "It gets colder, and the weather gets gnarlier the further you [travel]."

Then, on day six of the race and holding fast to second place, Team Dogsmile tragically experienced a catastrophic boat failure that caused them to abandon the competition and turn around. Jon and the rest of the crew were devastated, and they spent several "soul-crushing" days figuring out the logistics of how to get themselves, and their boat, back home.

Ultimately, however, as Jon reflected on the overall R2AK experience, he expressed his gratitude for the opportunity to learn and grow from the disappointment of not finishing and acknowledged the positive publicity that Dogsmile Adventures has received from the event.

Jon said he and the Dogsmile crew are determined to run it back, hoping to compete in the 2025 R2AK.

"Now being able to look back at it, it was awesome,” Jon explained.

“Jason said it best, 'We signed up for an adventure, and we got one.'

"It was full on, man," he continued. "And the story goes on."