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Most people do anything to avoid prison. I longed for it. I trained for it. And not a run-of-the-mill county jail, not even some barb-wired penitentiary surrounded by cornfields. Gimme legendary. Gimme Alcatraz. The conventional way to experience the notorious prison perched on an island in the San Francisco Bay is to board a ferry crammed with passengers looking forward to taking selfies within one of the more than three hundred cells. Lining up to get an Instagrammable shot beside a rudimentary toilet would have had me screaming, “Let me out!” But then escape had been on my mind from the outset. From 1934 to 1963, when Alcatraz operated as a federal prison, there were fourteen escape attempts involving thirty-six prisoners. All were caught, killed or presumed to have drowned, including Frank Morris and brothers John and Clarence Anglin whose bodies were never found after their famous attempt in June 1962. An escape requires careful planning. I was a regular indoor pool swimmer, submerged Band-aids and run-ins with the lane rope my only threats. I hadn’t been more than ankle deep in the ocean in two decades. Fish freaked me out. I feared getting tangled in sea kelp. I tried an open swim near home in British Columbia, lasting fifteen minutes before panic and the shivers sent me beach bound. The next day I bought a wet suit, a splurge for a one-time event and an admitted advantage over fleeing convicts. At dawn on an overcast September morning, I traipsed from my hotel down to Fisherman’s Wharf, staring down Alcatraz, the expanse of water between us a murky brown rather than ocean blue, a bit choppy but no whitecaps. Did I need to do this? Wouldn’t a plate of sourdough French toast be an adequate San Francisco memory? I walked off jitters, gazing at the sea lion colony at Pier 39, their movements kept to a minimum. Take it easy, they barked. If only. An hour later, I stood among three dozen chipper souls aboard Chucky’s Pride, each of us engaging in excited—or, in my case, nervous—chatter. “Is this your first time?” served as an easy conversation starter. It also helped me figure out who to follow. If that was even possible. “Keep the two apartment towers in view,” Coach Pedro from Water World Swim said. I eyed the Ghiradelli building by the towers. Prisoners had freedom dangling as a reward; I had chocolate. We came within a hundred feet of Alcatraz, as close as permitted by the National Park Service due to sensitive bird colonies. Coach Pedro reminded us that, pursuant to U.S. Coast Guard rules, if anyone struggled too much, they’d have to abide by any order to abort the swim and board a vessel. One by one, my pod of green-capped comrades made splashy exits from our boat. I jumped in after Len, a habitual escapee forsaking the wet suit for a Speedo. Show-off. On the periphery, kayakers and paddleboarders lurked, our would-be rescuers should the journey prove too much. The “Theme from Rocky” sounded our send-off. My arms smacked feet and torsos of other swimmers until there was distance between us. After five minutes, I looked back. I’d put no distance between the island and me. I swam on, swallowing salty water as I navigated swells. A kayaker shouted that I was drifting too far left; currents I could not detect. Ten minutes. Still no shaking Alcatraz from my wake. At one point, I considered waving for a rescue. No boaters were in sight, no Len, one green cap far ahead of me. I swam on, fifty strokes at a time before popping my head up to get my bearings. Eventually The Rock shrank. I trudged on, kicking harder as I imagined the skeletons of doomed escapees below me. “Jaws” and “Sharknado” whirled in my mind. Every so often, I spotted a green cap, bobbing in the water. You are not alone. At last, I swam between two piers, the water calming and my form becoming cleaner as I passed a pirate ship. I stroked until my right hand hit sand. Land ho! I did it. I escaped Alcatraz.