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Kimo Winterbottom’s obsession is to win Transpac. Safely.
Kimo Winterbottom has sailed all his life—at times at the highest levels of the sport. Olympic trials in the Soling, three times in the J/24 Worlds, racing the Maxi circuit in the Mediterranean, the Caribbean, Australia and San Francisco Bay. But it wasn’t until his father passed away in 2023 that his compass needle pointed offshore.
“Frankly, I was terrified of bluewater sailing when I was growing up,” he says. But his dad was really into it, crossing the Pacific 15 times in various campaigns. His father’s passing inspired Winterbottom to buy an Andrews 56 and sign up for his first offshore race—the 2024 Pac Cup. As Halawa crossed the finish line, he and his brothers, Michael and Jesse Winterbottom, spread their father’s ashes in a tribute to the legacy of bluewater sailing he’d newly inspired in them.
In what his dad may find an even more fitting tribute: “I now have an obsession to win Transpac,” says Winterbottom. After two Pac Cups and the 2025 Transpac, as he looks ahead to the 2027 race, his goal is clear: “I’m looking to win.”
What he’s learned is that at this level of offshore racing, cutting corners on the prep is not a winning strategy. “I discovered that ocean racing is a game of preparation. The more prepared boats have a tendency to perform better out on the open ocean. Safety is super important, which is why we have AIS transmitters and Spinlock PFDs for all the crew. We spend a lot of time talking about how we’re going to improve our performance in the Pac Cup and Transpac and other races. We’ve done everything from putting a new keel on the boat, new sails, new mast….You name it, we’ve done it in an effort to get lighter and faster.”
But that intense focus on improvements and performance can fall apart quickly without a proper insurance policy—something that has kept many skippers with bluewater dreams stuck at anchor. Finding adequate coverage has stymied Winterbottom, so he’s combined his sailing experiences with his 40 years of expertise in the insurance industry to create a new insurance product for sailors.
“We want to insure the boats that are better prepared with people who have resumés that reflect that preparation. These are safe risks over the years,” he says of Transpac competitors who fit the bill for policies underwritten by Bridger Marine Insurance, where Winterbottom is CEO. “I don’t think there are many CEOs that do what I do, so I decided that I could meet a need amongst my constituency.”
His development of an offshore insurance product was inspired by his own frustrations with fickle, inadequate coverage and his time offshore where unpredictability reigns. For example, he hit a whale on the way to Hawaii this year. The whale and Halawa both survived the encounter, but those are the types of unplanned events that insurance should cover when one ventures beyond the breakwater.
“We spent a tremendous amount of time constructing our policy form, engaging legal counsel, digging into our own experiences to make sure we had a policy form that we could be proud of and that responds to the needs of sailors,” he says.
What’s missing from most boat insurance policies? Mast coverage, international coverage if you wander beyond the territorial waters of the United States or cross the border in a race to Ensenada or Cabo.
“California Race Week will take you more than 12 miles offshore into international waters—these are the things we cover,” he points out. “Bridger Marine provides mast coverage of 50% of agreed value and subject to a rigging survey, and up to $1 million of liability coverage. We do not exclude any offshore races regardless of the length or position in international waters.”
Halawa is currently berthed at Waikiki Yacht Club while Winterbottom makes plans to compete in the 2026 Lahaina Return Race, and he’s locking in his 2027 Transpac crew, including navigator Mark D’Arcy, engineer Conrad Holbrook, his brothers Michael and Jesse Winterbottom, and David Rogers and his wife Taylor Joosten. “We’re a Corinthian program, no pros on the boat and I’m proud of that and we’ll continue that.” Corinthian doesn’t mean they don’t take the game seriously and try to elevate everyone’s skills to the highest levels.
“If your crew members on your boat haven’t taken Safety at Sea, I’d strongly urge you to do that regardless of whether Transpac requires it of every competitor on the boat. It’s just good practice and it’s a good investment of your time and your crew. If you think you’re prepared for the worst things that could happen on the boat, ask yourself: Do you know exactly where your life raft is?”
“Invest some time and money in safety. You’re your best insurance policy.”
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UPCOMING SEMINAR ON BOAT INSURANCE
Stay tuned for an announcement about an upcoming informational seminar with Bridger Marine, covering the issues to consider before heading offshore and the insurance products that might be available for you and your vessel.
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