On Sept. 9, a UC Santa Cruz student battled darkness and doubt to become the second person to ever paddle back and forth across the Monterey Bay.
At 12:56 a.m. on Wednesday, Sept. 9, 21-year-old UC Santa Cruz student Oliver Levine pushed off from Cowells Beach to begin an epic 48-mile, 12-hour paddle to Pacific Grove and back again.
He was alone on a 12-foot board with no support boat—just a barely functioning VHF radio for emergencies.
“When I started out, it was pitch black. About a mile offshore, the bioluminescence [from light- producing plankton] appeared in the water around me. It lights up everything that moves, so your imagination runs wild,” he says. “Your mind processes every little thing as a threat. Paddling alone at night out there…it’s not fun.”
It was only the second time a paddleboarder has completed a full lap in the Monterey Bay, which sits over a 2.5-mile-deep trench larger than the Grand Canyon. The first was in 2014 when Mike Dilloughery of Santa Cruz completed the journey on an 18-foot board. “If I’m being honest, part of me wanted to take the challenge a step further by doing it on a stock (12-foot) board,” says Levine. “The shorter board requires a lot more energy to paddle.”
Levine grew up in Santa Barbara and started paddling at 16. Early adventures included paddling out to the oil platforms off Santa Barbara and from Hollister Ranch to Point Conception and back.
“I love being out in the open water. The isolation is intense and really peaceful,” he says. “It’s the same as being alone in the mountains or something.”
In the fall of 2023, Levine moved north to attend university. Views of Monterey Bay from the UC Santa Cruz campus captured his imagination and planted a seed. What would it be like to paddle over that enormous, cold, deep trench?
In the summer of 2024, he learned about Dilloughery’s legendary 2014 paddle and decided he wanted to replicate it. He just had to wait for the right conditions.
“I needed a good, predictable weather window. Mike [Dilloughery] got caught in prevailing northwest winds on the way back and the chop was a nightmare. It took him an extra six hours or something like that,” Levine says. “I began looking for days when the bay was flat with no wind and no fog. When I saw those conditions, I’d look at the charts and check the models and see what conditions were creating that.”
Over the next two years, he started to visualize a predictable weather pattern. The key, Levine says, was hurricanes.
“I started watching for hurricanes moving up the coast. Those tropical systems can create windows when the tropical weather pattern briefly overtakes Monterey Bay’s normal conditions,” he says.
To avoid any risk of running headlong in northwest winds, which usually pick up in the afternoon, Levine decided to leave from Santa Cruz at 1 a.m. Yet when he started the paddle, he couldn’t see any lights on the other side. Fog, Levine says, is the most dangerous element of weather possible because it’s easy to lose one’s bearings and boat traffic won’t see a lone paddleboarder until it’s too late.
“I was 95 percent sure that it was just haze from [Hurricane] Marie or maybe even a little smoke from the Big Sur fires. I’d set my compass bearing the night before so I just decided to trust it,” he says. “The first 10 miles I was just paddling into pitch black, but slowly a bit of a glow appeared from the direction of the Monterey harbor.”
So what’s it like to paddle alone over the Monterey Canyon at 3 a.m.?
“It’s an experience like no other. There are these weird banging sounds out there. Like deep metal booms. I don’t know what that is,” he says. “And you’re on edge because you can’t really see anything other than spooky bioluminescence when something moves beneath you.”
At one point in the night, a whale swam directly under Levine’s board. He held his breath as the glowing outline of this giant slowly disappeared back into the depths.
When Levine landed on the beach at Lovers Point in Pacific Grove, he felt completely used up and wasn’t sure if he had it in him to make the return trip. But after locating his stash of food and water and using the bathroom, his optimism returned.
“The sun was rising through the clouds. It was really beautiful and re-energizing. On the way back, the conditions were sheet glass until the last mile or so. Just perfect,” he says. “I tell you what, it’s a lot more fun to paddle across [the bay] during the day.”
NEXT: Catch up on the latest news with NEWS BRIEFS
