High School Highs to Annapolis and Back

If there is one takeaway for San Francisco Bay’s high school sailors after racing in Annapolis, it’s a wish: more, please. Rhett Krawitt said, “It’s hugely valuable for a local team to get into the national scene. I learned so much, and it’s a win for the foundations that supported us, that supported the whole community.”

We might add, a win for the people who support the foundations, but we’ll come back to that. Northern California high school teams aren’t used to traveling farther than Los Angeles or San Diego. However, in April, Redwood High won the inaugural Northern League Championship title and a trip to the Phebe King Memorial Regatta on June 1-2. The regatta was sailed in Annapolis YC’s favored waters for dinghy racing, between the Severn Sailing Center and the US Naval Academy across the way.

The best thing about going to the East Coast, Krawitt said, “was sailing against a new group of people. I would love to go back for another chance to win.” His teammate Henry Vare added, “I was curious about the East Coast competition. It’s tough, but getting to know new people was the best.”

Yes, this sailing thing is about water and boats, but if you listen closely, it’s always about the people. Redwood placed sixth among 18 teams (including the 2024 national champions, Severn School). Redwood had top finishes, plus a few to make you wish that high school sailing would drop worst scores. (It doesn’t.) It’s not making excuses to recognize that Redwood’s sailors were new to the class they were sailing, suddenly new to a patch of water “blessed” with peculiarities, and not fully rested from a red-eye flight and a day of touring the Maryland State House and the Naval Academy. Back home, Redwood High was still in session. The travel window was short. But no regrets, just, “more, please.”

Easier wished than done, but you gotta start somewhere. The racing kicked off in 3-4 knots, but a lot of 8-10 followed, with highs of 12 knots. “When it fills there, it’s solid,” Vare said. But there was one wacky episode, as Krawitt described, “when the breeze was coming across Annapolis, so it was shifty, and then it split and was coming from the left of the peninsula that Severn sits on, and it was also coming from the right.” So, do you put it all on Red Four, or Black Five? Welcome to Annapolis.

There is no way to experience that except to go. High school travel regattas, however, are hard to come by. The Phebe King is a rare invitational. Otherwise, California high school teams have to place at the top of the Pacific Coast Championship to earn a place at the Nationals, and those top places are dominated by Southern California schools that proudly pump money and extra coaching into their teams. Placing top 10 at the PCCs is a frequent achievement for NorCal schools. Top five is a brick wall. It starts with the culture.

Sailing is not even an official sport on Doherty Drive in Larkspur, where Redwood shares a swath of the flats with four other schools. Official sport or not, the powers that be at Redwood High have seen fit to place the Northern League Championship trophy on display. We’ll call that a win.

It’s a special trophy, historic, repurposed for a new life. Five foundations joined forces to fund the travel regatta as a bonus, to inject a dose of energy into our youth sailing. This was a community effort that rallied all points of San Francisco Bay. The Richmond Yacht Club Foundation was quick to say yes to a proposal to send the Northern League Champions to Annapolis, no matter who that turned out to be. The Encinal Yacht Club Sailing Foundation was a solid supporter from the get-go in 2019, when we floated the concept, little imagining that 2020 would set us back four years. Peninsula Youth Sailing Foundation, which hosted the Northern League Championship, got into the game along with the robust St. Francis Sailing Foundation and Belvedere Cove. The San Francisco Yacht Club is home to Redwood’s team and to Belvedere Cove, and like all the foundations, they were unwavering even when we were swimming in unknowns.

For supporters of youth sailing, this was a thing of beauty, and it goes without saying, but it can never be said enough, that it is the people who support the foundations who are the “foundation” of it all.

So, 2025? It’s back to unknowns. We’re testing the breeze.

Listen to a conversation with Kimball Livingston on our Good Jibes podcast #143.