Doctor Fun's 20,000 Leagues Over the Sea

The 14 sailors aboard Van Ki Pass, a 65-foot Vic Carpenter design, get ready in Newport to race to Bermuda

Newport, Rhode Island, is synonymous with sailing. Everything about the place reeks of colonial American history and seafaring adventurers combined with nuevo-riche yachties sporting LaCoste shirts and silver BMWs. In 1906 some bored rich guy decided that a sailing race to Bermuda would tickle his fancy and thus one of the classic yacht races in America was born.

I arrive in Newport at 10 p.m. after a long day on planes, buses, and taxis. Liza greets me at her local watering hole and we eat, drink and talk until midnight before heading back to her condo. Finally I crash and sleep in until 8 a.m., which really isn't sleeping in much since it's still 5 a.m. Hood River time. After a quick bagel and cappuccino at the very Gucci Dockside Cafe, I head for the boat. I'm here to go racing, after all.

Van Ki Pass is a stunning piece of work that was completed in 1992. Built over a six year period by marine designer/builder Vic Carpenter as his personal racer/cruiser, she was launched from Canada on Lake Huron and sailed there until 1999, when Vic had a stroke and could no longer sail. When it became apparent that Vic wouldn't be sailing any more, she was moved to Newport to be sold, and there she sat under wraps for the next six years, with only her 90-foot spruce spar visible to the world until a curious yard worker looked under the covers and-Holy woodwork, Batboy!

Everything on the boat was perfectly preserved, from the incredible woodwork and finish to the brand-new suit of Vectran sails and lines. There were no shortcuts in the woodworking: The inlay work on the counters, tables, and even the transom, all done by Vic himself, is worthy of any art gallery.

The design is of a moderately spartan racer/cruiser (small galley and dinette; 12 pipe berths but no opulent master suite; two small heads without showers; no watermaker, autopilot, genset, or other cruiser benefits; small water and fuel tanks; and a flush, utilitarian deck plan with no comfy seats or shade). This is in stark contrast to the incredible finish work that abounds inside and out. The hull is 1.5 inches thick with several thousand laborious coats of varnish. I sure don't want to be around when it's time to refinish her.

Liza Baldwin is one of a family of seven all born and raised in Newport, the self-proclaimed sailing center of the universe. Apart from a 25 year stint in New York, where she worked as a commodities trader, she's lived here all her life. She knows everyone.

A veteran daysailor, Liza has always wanted to do the Newport-Bermuda Race, considered--with the Fastnet, the Transpac, and the Sydney-Hobart--as one of the must-do events for every serious yacht racer. She's watched the fleet leave Newport harbor for 50 years: some day, I'm going to do that!

When Randy West, a veteran race and charter skipper who's sailed extensively with Liza, heard about Van Ki Pass (which was actually christened with the incredibly tacky name of Passing Wind), he got in touch with Liza. You want to race to Bermuda? Well, this is your boat.

One look convinced her that this boat was a true gem in the rough. Although not really that rough. She arranged to have a full survey, and if the boat passed inspection (she did), Liza planned to charter her to do Newport-Bermuda. She hired a crew, and for the next two months they worked full time to get the boat ready. Although Liza had never been offshore before, this was her chance. Trial by fire. Spin the wheel, and hang on.

Liza is a gambler. She gets up early each day sits and down in front of her computer, where she logs in and begins her daily session of trading S&P 500 futures. This is a dangerous game indeed, but Liza is good at it. Good enough that she's now able to buy a 65-foot sailboat and hire a crew to race with her in Newport and in the Caribbean all next winter. As she sits at her computer making bets on minuscule movements in the world economy, the crew is busy getting the boat ready at the dock just outside her waterfront condo. She glances out the window and smiles, perhaps oblivious that the crew is spending money on last-minute parts every bit as fast as she's making it. The daily haul from the local chandleries includes piles of $400 snatchblocks, spools of high-tech line, new sails, safety gear, four new sails, and other assorted necessities for offshore racing. This is the real deal.

"You know," says Liza with a mischievous smile and sparkling eyes, "we could win this thing. We really could."

And she's serious. She doesn't just want to play the game--she wants to win. Toss the dice, take a chance, go big or go home. Woohoo!

As the days wind down before the schedule race start, we get the first weather forecast. Oh, great, just great. The very first hurricane of the year has just formed in the Gulf of Mexico and is headed right smack into us. Not an inch off. With sustained winds of 75 mph, it isn't a whopper, but Hurricane Alberto is just enough of an issue that it could severely impact the fleet. If the race leaves as scheduled and the storm continues north, it will just leave ugly, choppy seas and light winds in its wake. If it grows, slows down, or turns around, it will hammer the fleet. We track its course as we busily ready the boat.

Our crew of 14 includes nine professional sailors; three French girls, who are the cooks; Liza; and me. While I've been offshore a few times, I've never done any racing other than some casual beer-can afternoons scooting around the buoys in the sunshine. I'm glad to have a bunch of veterans on board, but I'm worried that my extremely light sailing resume will quickly become apparent. Which side is starboard again?

The last few days on shore are spent doing all the last-minute chores and tweaks inherent in such an undertaking. Looking around the boat, and remembering how it took me two long years to finally get my boat outfitted as I wanted, I find it hard to conceive how we can possibly be ready in just three more days. My mental list of necessities quickly runs into adding a few more weeks of preparation. And we haven't even been out sailing yet as a team.

On my second day, we finally head out later in the afternoon for sailing. I look around at the incredible rat's nest of lines and hardware, not to mention the winch farm of--no exaggeration--25 winches scattered around the small cockpit. At least a dozen lines lead back into the pit, where I'm stationed doing a variety of jobs depending on the need. Since I'm surrounded by a crew of sailing pros who've spent the last two months getting the boat ready, it's assumed I know what the hell I'm doing. Fat chance. Listening to the discussion of the intended plan of attack for our first spinnaker set, I'm immediately aware that I have absolutely no business whatsoever being in charge of anything at all having to do with control or responsibility for a 50,000-pound boat worth $2 million.

We spend three aerobic hours zinging around the bay. As soon as I'm comfortable with one set of instructions, I'm given another significantly more complicated and confusing set to master, replete with all those arcane and bewildering nautical expressions: spinnaker guy (is this a male spinnaker?), lazy sheet (what I sleep on when I've avoided work?) and topping lift (some sort of chocolate-flavored speed?). I simply put my head down, shut my trap, and do what I'm told. For once in my life.

Every single yachtie on the planet has his own way of coiling a rope (oops, I mean a line), and this group is no exception. I try three of my favorite techniques and am admonished by someone for each and every one. I give up and just let the lines stack up in a pile. I watch as one person makes a coil, then two minutes later, someone else will pick it up, glance around in mild indignation, and recoil the entire line. Sailors, I've learned, are staunch individualists.

And macho. did I mention macho? There's more strutting around here than the gorilla cage at the zoo. Everyone is someone, or at least they want to be. Everyone knows someone, or at least they can drop names like I drop popcorn at the movies. During a race like this, everyone talks sailing, even if they don't have the slightest idea at all what they're talking about (like me). I talked to one woman who had no idea where Oregon was (somewhere near Colorado, right?) but insisted that she was a good friend of "Dennis Conners." I told her I was his nephew, and did she know that he was actually gay?

Every night is a big party. Newport is abuzz with yacht-racing activity, and it's growing into a frenzy with this race. The crews of big and small boats rush to do last-minute preparations, and sailors cut loose at night before they're on the alcohol-free program for a few days. I think there's enough residual booze in our crew to certainly last through the race. We're all trying to properly hydrate, you know.

On Wednesday, five of us go to an all-day Safety-at-Sea seminar that covers everything from seasickness to helicopter-rescue techniques. According to the seminar leader, only two boats have been lost and only one person has died in the 100-year history of the race. And it's only been postponed twice because of weather. I passively consider the hurricane storm track that's coming our way as we learn about storm survival, onboard fires, and other pleasant topics.

That evening, we attend the Dark and Stormy party, which consists of 1,400 sailors getting ready to head to sea interspersed with a few hundred hangers-on, including a veritable flock of local ladies dressed to the absolute hilt looking for rich sailor boys to hustle. The party is located in one of the local boatyards. Now, when I think of a "boatyard," I think of dirty machinery, crumbling buildings, and junk everywhere. But we're in Newport, and the nearest thing to junk here is a crooked street sign carved from Antiguan teak. The docks of this "boatyard" are filled with $10 million yachts, and right smack in the middle of the party, up on stands, is a 160-foot sailboat that has to be worth at least $20 million. It won't be in the race since it's getting its biannual refit (probably costing another $1 million). The prop on this boat probably costs more than my entire boat. It's a somewhat humbling experience just to walk among this forest of carbon fiber and Kevlar.

The 120-foot racing cat Orange II is sitting at the dock, getting ready to head across the Atlantic for a record-breaking attempt whenever the conditions look right. Orange II, the size of a small city, will do 40 knots with a crew of just eight. I wanna go on that boat!

There are another dozen high-tech boats, termed so because they have all the latest high-tech innovations, including canting keels, variable hydraulic water-ballast systems, for and aft rudders, wing masts, and other assorted engineering novelties that one day might find their way into the average mom-and-pop boat (which, by that time, will cost as much as a house does now).

One more day of prep, and then we jockey for the start with 260 other boats on Friday morning. I sure hope it's a big starting line. That evening, Marco arrives. Who's Marco? Yet another super-experienced yacht racer? No, Marco is our personal hair stylist, and Liza has flown him in from St. Barts to give us all a nice trim so that we look good at the start. Marco used to cut the Clintons' hair when they lived in that big house in Washington (although he still visits Hillary in New York occasionally when she flies him in for a quick buzz cut). So Marco sits each of us down on the dock and goes to work, scissors blazing and hair flying. The other crews look on with a combination of awe, jealousy, and indignation. I only want to know one thing: Where the hell was Marco-the-barber-of-the-rich-and-famous when I still had hair? Now all he can do is cut an inch off my fading ponytail. Hell, I could do that myself! Nevertheless, we look marvelous!

Our captain is Randy West, a veteran of over 100,000 miles of ocean cruising and racing over the past 30 years, including six transatlantic crossings. We're divided into two watches of six crew, with six hours on and six off. Every day. Until we get there. The other watch captain is Tom Perry, who skippered both Endeavor (120 feet LOA) and Shamrock V (129 feet LOA), two of the largest classic J boats. Tom has over 250,000 miles of open-ocean experience. Between them, we seem to be well covered.

On race morning, the harbor is alive with boats and crew. We're all issued our crew uniforms, which consist of more clothes than I've brought with me: two fleece shirts, long- and short-sleeve T-shirts, polo shirts, shorts, caps, and, yes, wool berets (presumably for throwing in the air, graduation style, as we cross the finish line). Everything is embroidered with our boat's name--so when my soggy body is found floating in a few months, they'll know where I came from, I suppose. The biggest decision of the day may not be what headsail to raise but what shirt to wear. We all must look quite dapper, you know.

Sleek ULDB racing boats slip past us at the dock, their crews also nattily dressed in matching uniforms. "Don't hit us!" I yell. "You'll get splinters!" Ha ha, I'm a real crack up. Get it? "Crack up?" Ah, never mind.

Finally, we get last-minute shore leave (sailor talk for standing on dry land wondering what the hell you've gotten yourself into) for updating wills and eating something quite colorful--so when it comes back up in a few hours, at least it will look pretty. I leave everything I own to my dog, then eat a jar of yellow curry chutney washed down with a Dr. Pepper. I'm ready!