Swell Adventure

But this latest front door is my favorite. Maybe it's the harbor seals that pop their heads out of the murky green on my way in, or the view of the huge San Francisco skyline. But I think it's the fact that the door to my sailboat, Dulce, is so damn difficult to open, especially if you've had a few drinks. You have to disassemble three awkwardly fitting wooden planks and climb down a ladder, fireman style, into the cabin. From the moment you set foot on Dulce, you're on an adventure.

By renting this boat, my plan is to realize my life-long dream of becoming an expert seaman, a Jack Sparrow-meets-Jacques Cousteau type character, a man who shies away from no storm, no wave, no complicated front door.

Before taking to the water, I need to learn a little about San Francisco's sailing culture. So I've been strolling the Marina docks, striking up awkward conversations with guys who all seem to be part of elite yacht clubs and want to discuss Larry Ellison's sailing lawsuits. 

I try to shift the conversations to strictly sailing, only to realize I can't begin to hold one. Sloop, jibe, bearing off? Why don't they speak English? Plus, with my ripped Vans and shaggy hair, I don't quite fit these sailors just-stepped-out-of-a-J.Crew catalogue look. 

Fortunately I'm not the first to feel like an outsider. I'm reading Richard Henry Dana Jr.'s sailing classic, Two Years Before the Mast, in which Dana writes that "while I thought myself to be looking as salt as Neptune himself, I was, no doubt, known for a landsman by everyone on board.... A sailor has a particular cut to his clothes, and a way of wearing them which a green hand can never get." 

From the look of the guys on the Marina docks, sailor styles have changed from what Dana calls "trousers‚ long and loose round the feet‚ and superabundance of a checkered shirt," to Ray Bans, designer jeans, and slip-on canvas Clarks. But I figured Dana's assessment that "there is not so helpless and pitiable an object in this world than a landsman beginning a sailor's life" hadn't changed. 

I was definitely helpless and pitiable. So I drove over to West Marine, the premier boating shop in the Bay Area, to see if I could get some advice on where to start this sailing venture, and maybe some new shoes too

"I want to learn all about sailing," I told a West Marine manager with a tan to make a Hawaiian Tropic model jealous.

"Well, there are plenty of schools in the area," he said, continuing to rearrange products.

"Yeah, but which is the best?"

He shot me a suspicious look, but then scanned my torn shoes and waved me over to the other side of the store. "This is Adam," the manager said, introducing me to a young employee who was also sporting torn Vans and shaggy hair. "He'll tell you what you need to know. And by the way, this is how sailors look. Torn up shoes. We're poor. We spend everything on our boats and have nothing left."

I suddenly liked this manager. Apparently there is a bit of a rift between the working-class sailors who live on their boats and the yacht club set I'd been trying to schmooze with. And according to this manager, those guys looked less like the real deal than I did. Ha! Things were looking up. I didn't need any new clothes, and Adam was cool: a surfer who also lived on his boat and who recently qualified to race to Hawaii single-hand, meaning alone.

He was instantly my hero. We talked breezily for 30 minutes comparing surfing to sailing. Suddenly I was in. And even better, Adam had only learned to sail four years ago, which made me think my inner Jack Sparrow might just take over at any minute, without warning.

"How'd you learn?" I asked eagerly.

"I just went out," Adam said, as if sailing around San Francisco, known, with its super rough currents, to be one of the most difficult sailing locations in the world, was like going for a jog. "I just did it. I volunteered on a crew and then bought a boat."

"Nice."

"I'll take you sailing," he said. "We'll just need to find the right day."

"Sweet."

Since all guys with shaggy hair and torn Vans are flakes, I wasn't shocked when Adam got sick on the day of our sailing lesson, then, when we rescheduled, weaseled out again by saying he had to get his boat ready for that whole solo sail to Hawaii thing (oh, I'm sure that really takes a lot of preparation, Adam!).

I could just do it too. I called the Bay Area sailing schools until one really leapt out at me: a private class with Captain John Yalda of The Temptation, a beautiful 37-foot sailboat docked right in the Marina. John told me he grew up sailing in Siberia (and who knew the ocean isn't just a frozen block up there?), contracted for the U.S. Coast Guard and Homeland Security, and in his spare time volunteered helping locate dead bodies in the Bay. Could you get any more hardcore?

I arrived at the Marina on a sunny fall day proudly wearing my ripped shoes. John didn't look at them. He seemed to favor the J.Crew look. Oh well. John was friendly. He'd just come back from taking a couple out for an "engagement" sail and fortunately the woman had said yes. "Sometimes they don't," John said straight-faced, "Which is really awkward because you're stuck out there for a while."

I laughed, but I was only half present. Something about Temptation's big shiny steering wheel was giving me visions of grabbing it and barking orders like "Lower the starboard bow you dogs!"

"Where would you like to go?" John asked.

"Under the bridge," I said with surety.

"Bridge it is."

I was getting all psyched thinking about leaping around Temptation, throwing lines and screaming. But as we motored out, I realized that most of this lesson was going to be memorizing vocabulary that sounded like a Moby Dick user's guide.

I remembered the ones with little tricks: Portside meant left because "there's never any port left in the bottle," and Starboard meant right because "the stars are always right". Also, the three sides are called the leach,  the foot, and the luff, and the corners are called the head, the clew, and the tack. "So imagine your sail is Robin Leach from Lifestyles of the Rich and Famous," said John. "But those British guys have big heads, even though they don't have a clew. And if you tickle, or tack, their foot, they will luff."

"How'd you come up with that?" I asked.

"Oh, you know, I just smoked a joint and it came to me. Just kidding, I don't know."

Sailors rock. Even the Siberian ones are laid back.

Once we were under the Golden Gate‚ that grand steel underbelly shadowing us like some Art Deco god, John let me take the helm and "come about" all by myself, which meant making Temptation do a full 180. Yell "coming about," John shouted as the boom swung from one side to the other. 

"COM-ING ABOUT!," I screamed with obvious pride.

Lord knows I couldn't have kept Temptation afloat without my Siberian captain instructing me in every detail. But behind the wheel I was definitely feeling my inner pirate. I let out a muffled call while John seemed out of hearing range: "Scrub the decks you scallywags!"

"What's that?" asked John.

"Oh nothing," I said.

He looked perplexed, but I didn't care. I was freaking sailing. And this was just the beginning.

DO IT YOURSELF
Craving to find your own inner pirate? Unless you’ve got a boat of your own, you’ll need to join one of the many sailing schools. At $125 per-hour Captain John Yalda ’s classes are on the pricey end, but you get the Siberian expert’s total personal attention (plus his creative memorization techniques) and Temptation is about as state of the art as it gets.