I guess it's fitting that a police boat is following us. I'm not sure why they're here, but every time I pop my head up to see how far we are from the island, those black-suited men with guns are staring at us like we're crazy. And they're probably right.

I’m attempting to swim out and back from Alcatraz with Jamie Patrick, one of the world’s elite ultra-swimmers, a man who, among many great races, has finished a triple Ironman Triathlon (that’s a 7.2 mile swim, a 336 mile bike ride and a 78.6 mile run) without stopping, and who is now training to swim the length of Tahoe three times this August, which will set a new world record for lake swimming at 66 miles. (He’s doing it to raise money to keep Tahoe clean.) I think just by hanging out with this man, I’m crazy by association. The police should be involved.

This is how you start thinking anyway when you have an ice cream headache the size of a frozen watermelon and you’re swimming toward an island that’s legendary for being surrounded by 20-foot Great White sharks. The sharks were actually a myth designed to scare prisoners, but Great Whites do come in the bay occasionally to feed, and ocean myths have a way of becoming especially eerie when you’re a mile from shore.

We’re definitely crazy, all five of us in our fluorescent pink swim caps, a crew that also includes Greg Larson, a dentist who was formerly on the US Olympic swim team, Mark Lukach, a school teacher and swim coach with a penchant for bodysurfing waves three times his height, and Kelly English, a competitive runner who is in a kayak making sure we don’t drown. (Thank you Kelly!)

But we’re not just crazy. We’re poorly organized. Jamie, who has done this swim more than 20 times asked his dad, a seasoned sailor, what the ideal tides would be to swim to and from Alcatraz on a Sunday. The verdict was 8:45 am. We’d enter at slack tide, Jamie said, with a minor current pulling us toward the Golden Gate Bridge, then return as the tide began coming in and get pushed into shore.

Only problem is, Jamie’s dad accidentally got the tides mixed up —or that little tsunami that passed through the day before screwed everything up. So as we were leaving Aquatic Park just 15 minutes ago, the tide surge was clearly pushing us back toward the beach, away from Alcatraz.

Jamie asked one of the Dolphin Club members in his skiff if it was a good time to go for the island. “Sure, if you want to end up at The Bay Bridge,” the man replied, adding “there’s a full flood right now,” meaning that the tide was roaring in through the Gate so fast it would push us practically to Berkeley.

Lovely.

We swim another 10 minutes out, sinking into a meditative rhythm, when a wooden skiff pulls up next to us. “Hey guys,” says the same guy from the Dolphin Club. “So what do you guys plan on doing if a freighter comes through?”

We all look at each other, embarrassed, waiting for someone to pipe up.

“Cause I’m just saying,” he goes on, “we work really hard let the Coast Guard know anytime we’re doing a swim. Those freighters can’t stop and they can’t see you. We also have radios to communicate with them. You guys have a radio?”

“Don’t we have a radio, Jamie?” I ask.

“No, we don’t have a radio,” Jamie says.

So now we all have an image of a thousand-foot, gagillion pound mass of steel running us over and chewing us up in its planet-sized propellers.

“Whatever you decide, have a good swim and be safe,” says the man, turning around, which is basically like saying to some hikers in the mountains of Afghanistan, “Keep going if you like torture, beheadings and YouTube videos.”

“Yeah, that’s pretty serious,” Greg says to Jamie. “He’s probably right.”

Jamie agrees and we cheerfully decide to turn back. We aim back for Aquatic only to realize that in the five minutes we stopped swimming to deliberate we’ve been sucked at least a few hundred meters east.

“Really?” says Jamie, genuinely surprised. In all his swims he has never heard this and there aren’t exactly signs posted.

I think it’s a bit odd. You can swim out into the middle of the San Francisco beaches in surf the size of four story buildings. But try to swim in the Bay and you need to practically get a permission slip from the mayor.

“Well, I’m not going to say anything,” laughs Greg as the cops leave, “because you wouldn’t believe the stuff Jamie and I have planned to get Jamie ready for the Tahoe triple.” As one example of many, they’re planning on swimming the entire length of Clear Lake for the first time in history, a distance of 19 miles, just short of the English Channel distance. You know, fun stuff like that.

I used to hear about people running across countries or biking a thousand miles and think, Why – do you just like pain? But after today, I might be beginning to get it. In a world where everyone is saying no — in a world where you need a permit to swim in your own Bay — there’s power in defiance. In that kind of world (and sorry for using the Nike phrase here) just doing it is a service, a work of art that says, You know what? Watch me.

If you don’t want to be chopped up by a freighter or yelled at by the police but you do want to swim from Alcatraz, the Dolphin Club accepts new members once a month at their board meeting and they swim from Alcatraz frequently, and safely – as safe as swimming in the Bay can be anyway. Just show up at 6:30 p.m. on the third Wednesday of the month. Bring a check for $326 to cover the first six months' dues, a refundable key deposit, and a nonrefundable initiation fee. You’ll sign your life away – sorry, no lawsuits for elephant seal or shark encounters – but at least they have radios. And post-swim hot tubs.