Imagine standing on the precipice of a vast, cold expanse, preparing to embark on a solo journey that few would ever dare attempt. This isn’t a supported expedition with a crew and a safety net; this is a personal pilgrimage across one of the deepest, most dynamic bodies of water on the planet. For Mike Dillery, a lifelong Santa Cruz surfer and dedicated prone paddleboarder, this was simply the next logical step in a life defined by the ocean. He didn’t just paddle the 25 miles across the Monterey Bay—he turned around, refilled his bottle, and paddled back, completing a grueling 55-mile double crossing alone, unsupported, and fully immersed in the raw, challenging beauty of the Pacific. This incredible feat encapsulates Mike’s dedication to finding the deepest possible connection to the water, a connection that began decades ago on the iconic waves of Northern California.
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Episode #2 – Coming Soon to This Ocean Life Podcast
From Steamer Lane Grom to Ocean Endurance Legend
Mike Dillery’s deep relationship with the ocean began in the heart of Santa Cruz, California, where he was born in 1965, growing up in the thick of a pivotal era for surfing. His formative years were spent navigating the legendary lineup at Steamer Lane, a proving ground that demanded both skill and respect. He was part of what he calls the “last hurrah generation,” witnessing firsthand the rapid evolution of surfing from the late 1970s through the 1980s. This was a time of radical transformation, moving quickly from single-fin boards to the revolutionary twin fin designs that changed how waves were ridden, and Mike was right in the middle of this seismic shift.
Growing up around the established hierarchy of the Lane meant learning profound lessons about ocean etiquette and earning one’s place in the water. Mike absorbed the unspoken rules of the lineup, understanding that respect was paramount, and that any attempt to “post up” without paying dues would be swiftly corrected. This environment instilled in him a deep reverence for the ocean’s power and the community that surrounds it, teaching him how to read not just the waves, but also the dynamics of the water world he inhabited. While he mastered the powerful, rail-focused style of surfing that defined his era, Mike also sought new ways to engage with the cold, powerful waters of the Monterey Bay. This drive led him to prone paddleboarding, a sport that offered a unique blend of physical challenge, solitude, and the ultimate opportunity to achieve an ocean flow state far from the crowded coastline.
55 Miles of Solitude: The Monterey Bay Double Crossing
The idea for the double crossing wasn’t a sudden impulse, but rather an ambition that grew quietly over years of single crossings. Mike had paddled the 25 miles from Santa Cruz to Monterey several times, yet the thought of turning around and immediately heading back represented the ultimate personal challenge. The opportunity presented itself during a rare stretch of “earthquake weather,” where the Monterey Bay lay flat and glassy for days on end. Recognizing the perfect conditions, Mike made the decision: he would go, and he would go alone. He duct-taped his water bottles and food supplies directly to his 17-foot prone paddleboard, accepting the extra weight and the reality of being completely self-sufficient.
Starting before dawn near Santa Cruz, the initial leg was pure bliss, a smooth glide across sheet glass water, accompanied by the stunning sight of the bay lighting up behind him. As he paddled, he was treated to an incredible spectacle of nature, dodging fishing boats and witnessing massive blue whales breaching and feeding around him, a reminder of the raw, untamed ecosystem he was traversing. After five and a half hours, Mike reached the Monterey side, pulling into Lovers Point. He refused to touch land, instead quickly engaging a kind woman at a snack shack to refill his bottles and exchange a few words before turning back toward the open ocean. This moment was the true pivot point of the challenge, transforming an accomplishment into an endurance test, and it was here that the conditions took a dramatic turn.
Finding the Rhythm in the Wind: The Meditative Power of Prone Paddling
As Mike turned north, aiming back toward Santa Cruz, the wind kicked in with brutal force, turning the glassy surface into a churning mass of whitecaps. The wind hit his right shoulder, threatening to push him deep inside the half-moon shape of the bay, away from his destination. This was where the physical challenge transformed into a profound mental crucible, a deep dive into the ocean flow state. Mike was forced to dig deep, pushing against the rising swell and battling the current, often feeling like he was making no visual progress for hours. The struggle was compounded when his music—his primary source of distraction and motivation—died completely, leaving him alone with his thoughts and the relentless rhythm of the paddle stroke.
For two arduous hours, Mike felt stuck over the deep Monterey Trench, fighting the wind and the upwelling, locked in a battle of wills. This period of isolation and extreme effort became profoundly meditative, a place where he processed deep emotions and found unexpected clarity. The intensity of the physical effort demanded total focus, forcing all other concerns to fade away, leaving only the present moment and the necessity of the next stroke. This is the essence of prone paddleboarding as an endurance sport: the sustained, repetitive motion under duress strips away the ego and demands absolute presence. The ultimate relief and inspiration came in the form of his friends, Zach and Matt, who, worried by his lack of tracking signal, found him mid-bay on a boat, delivering cheers and jokes that renewed his spirit for the final push. After nearly 12 hours of continuous paddling, Mike finally landed back in Santa Cruz, having completed one of the most remarkable solo Monterey Bay Paddle challenges ever attempted.
The Ocean Flow State: Where Challenge Meets Clarity
For Mike, prone paddling and surfing are more than just sports; they are essential rituals that anchor his life and provide a necessary counterpoint to the demands of the modern world. The meditative aspect of paddling far out to sea, alone with his thoughts, is his ultimate form of decompression. He describes it as his “D-commute,” a mandatory ritual prescribed even by his wife before he’s allowed back into the house after a long week. The ocean acts as a level-setting force, demanding respect and providing unparalleled fulfillment.
His involvement in the Ghost Riders Waterman Club and the organization of the Davenport Downwinder race further underscores this passion, emphasizing camaraderie and personal challenge over cutthroat competition. Mike finds joy in racing against his own time, striving always for self-improvement and pushing his physical boundaries. His story is a testament to the profound connection that can be forged through intense, immersive ocean experiences. Whether he’s riding the waves at Steamer Lane or battling the winds mid-bay, Mike Dillery’s life illustrates that the greatest rewards come from embracing the challenge, finding the rhythm, and committing fully to the finding flow in the ocean. His current ambition—a solo swim across a portion of the bay—proves that for those who truly love the water, the search for the next great challenge, and the next deep flow state, never truly ends.