For me, the Newport Bermuda Race has always been about family. Over the years, my children, grandchildren, my brother Peter’s children, and even their grandchildren have joined me aboard my J/46 Breezing Up. Together, we’ve earned podium finishes in all but one race and have been honored with the William Glenn Family Participation Trophy several times.

Winning the Glenn Family Trophy means as much to me as any silver — because it celebrates the spirit of sailing together across generations.

Now, with 20 Bermuda Races under my belt, I take the plane while my daughter Tori skippers the boat and my son Ben serves as navigator and strategist. Last year, eight family members were aboard, proudly carrying on the tradition. Nothing gives me more pride than watching the next generation embrace the race with the same enthusiasm and teamwork.

Our crew is a true mix of ages and experience. The younger sailors know the systems inside and out and jump eagerly into every sail change, while I bring decades of confidence in Breezing Up’s capabilities — honed from living aboard through five winters in the Caribbean. Everyone brings something important to the table: we share the helm every 30 minutes and take turns cooking. Good driving and good food keep morale high — the secret to a happy ship.

The name Breezing Up honors my great-grand uncle Winslow Homer’s famous painting, which hangs in the National Gallery of Art. To me, it’s more than a name — it’s a reminder that the essence of this race has always been the same: seamanship, family, and joy in the challenge of the sea.

Most important of all is being out on the ocean with family. It’s an honor every time. That’s what makes the Newport Bermuda Race special, and why I’m proud to serve as President of the Bermuda Race Foundation. My wish is to ensure that this offshore tradition continues to inspire generations of sailors — just as it has inspired ours.