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A grieving mother, a lost daughter, and a 30-mile bike ride into the Pacific

To keep a promise to her daughter, a bereaved mother attempted a treacherous trip from Sausalito to the Devil's Teeth.

A person rides a water bike on a calm sea during sunset, with a cloudy sky and hills in the background, creating a peaceful and scenic view.
Jessica Schiller sets off on a 60-mile voyage to the Farallon Islands and back aboard a waterbike. | Source: Thompson and Homonnay

Just before dawn, under a sky full of stars, Jessica Schiller waded into the dark waters of Richardson Bay. Dressed in cycling shorts and a light windbreaker, she climbed onto a waterbike — essentially a bike perched between two large pontoons — and began pedaling.

After a few practice loops around the marina as the sun rose Friday, she waved to supporters on the shoreline and set off for what would be a daylong trek, with the Golden Gate Bridge twinkling above her.

Her goal? The Farallon Islands, also known as The Devil’s Teeth. A remote, rocky outcrop 30 miles west of San Francisco, it’s a place off-limits to all but biologists due to its abundance of biodiversity. 

Rare seabirds nest there and the area is famous for its great white sharks, some as large as 20 feet.

“Last year they saw a record 78 adult great whites,” Schiller said. “I have someone who will be solely on shark watch as we get closer to the islands.”

October is prime time for sharks, drawn by their favorite prey: northern elephant seals. There are so many fins in the water that people sign up for shark-viewing tours across the same waters she’d be in.

Schiller was nervous, but undeterred.

“There are lots of things that are riskier,” she said.

Two years ago, her 20-year-old daughter Naomi died of a fentanyl overdose in Marin County, after years of struggling with addiction. 

“Losing my beautiful, kind, daughter really put me in a dark place,” Schiller said. “It was devastating. …  Losing a child takes all the light and purpose out of living.”

A person rides a water bike under the Golden Gate Bridge at sunset, with dark hills in the background and gentle waves on the water.
Jessica Schiller departs for her 60-mile waterbike ride to the Farallones. | Source: Thompson and Homonnay

Determined to save others from similar heartbreak, Schiller has committed herself to raising awareness about opioid addiction.

“I don’t want to see another kid or adult dying from a substance,” she said.

Naomi had struggled since she was a sophomore, but there had been few resources.

“We need to encourage people to talk more with their kids, to take the shame out of it,” she said.

Just about a decade ago, Schiller founded the eponymous Schiller Bikes as a way to circumvent bridge traffic by biking over water.

“Everyone laughed at me,” she said. “Some called it the dumbest idea ever.”

A person rides a pedal-powered watercraft on the blue sea, with rocky islands in the background under a clear blue sky.
Jessica Schiller approaches the Farallon Islands atop a Schiller Water Bike. | Source: Thompson and Homonnay

But her children believed in her vision. In fact, it was Naomi who suggested the daring trip to the Farallones.

“She thought it would be awesome,” Schiller recalled.

Though she promised Naomi she’d make the trip, life got in the way — until now.

“This ride is centered around the promise that I made to my daughter,” she said.

To honor Naomi’s memory, and raise awareness for Shatterproof, a nonprofit focused on treating and reducing stigma around substance abuse, it was time to fulfill that pledge.

The first few hours went smoothly, she said, but then rough seas set in, with 10-foot swells tossing her bike around like piñata.

“At times it was like riding a bucking bronco in a rodeo,” she recounted. 

At one point, a pod of silvery dolphins raced alongside her, their fins shimmering as the sun hit them. She passed through swarms of deadly, diaphanous jellyfish lurking in the water. Occasionally, a whale breached, its huge form stirring the water as it took a breath before diving down again.

When she finally reached the Farallones, Schiller took a moment to remember Naomi, honoring her memory by taking a few snapshots with her daughter’s old Minolta camera.

She returned to Sausalito around 6 pm, exhausted from her twelve-hour journey. “I’m glad I could keep my promise to her,” Schiller said. “This is a story about hope, and finding the courage to persevere and thrive—even in the face of the unthinkable.”

A person is pedaling a water bike on the ocean, wearing a light blue shirt, black and purple shorts, and sunglasses, with land faintly visible in the background.
Schiller is the CEO of Schiller Bikes, maker of durable, floatable waterbikes. | Source: Thompson and Homonnay