Adventurer's Bucket List: Swim to Alcatraz

Duncan Penn of MTV's "The Buried Life" suggests a swim in the treacherous San Francisco Bay.
Duncan Penn's Bucket List Swim to Alcatraz
Duncan Penn takes no prisoners © Courtesy of Duncan Penn
By Kitt Doucette

Duncan Penn knows a thing or two about bucket lists. Along with his younger brother and a couple of childhood friends, they set off on a quest to cross as many items off their bucket lists as possible. Not content with just achieving their own goals, the four friends vowed that every time they crossed something off their lists they'd help a stranger cross something off theirs as well. The ensuing adventures became a show on MTV called “The Buried Life,” which launched the boys from Victoria, British Columbia, into stardom.

Penn and the Buried Life crew are still at it, ticking off bucket list items on every continent. "My bucket list is always growing," explains Penn, who's played basketball with President Obama and skydived wearing a suit. "There are so many amazing things to do, places to go and people to meet. The more I get to see and do, the more I want to help others follow and realize their dreams."

What you should do:

Swim to Alcatraz without a wetsuit.

“It was one of the hardest things I've done, largely because I didn't train, which was a big mistake,” Penn says. “It was 54 degrees but I didn't notice the temp after the first five minutes. The toughest part is the open water — the waves throw off your timing and your stroke. You get waves in the face and swallow water. It was hard but also incredibly rewarding.”

Duncan Penn's Bucket List Swim to Alcatraz
Bad place for a cramp © Courtesy of Duncan Penn

How you can do it:

“Find someone who has done it or has experience overseeing it,” Penn advises. “Talk to people, get advice — there's lots of info online. There are groups that do it, so it would be good to team up with them. You need to do it when the current is right or it's almost impossible.

“It's best to do it with a boat to protect you from other boats and in case something goes wrong. There are sharks on the other side of the bridge but they don't come through, apparently. There's never been an attack inside the Bay. That's what I kept telling myself, at least.”

Duncan Penn's Bucket List Swim to Alcatraz
Always swim with a buddy © Courtesy of Duncan Penn

Planning resources:

Roots Rated has an article that answers a lot of questions and doles out some good advice.

Make the journey in the Alcatraz Sharkfest Swim or the Escape from the Rock Duathlon.

Water World Swim organizes training and Alcatraz swims every month.

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