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Ever since first stepping on board a sailboat 15 years ago I have longed for the day when I would have the time, energy, courage and stupidity (not to mention the money…) to buy a boat. Over the years I sailed when I could; on charter boats, as crew on various friend’s boats, day sailing and occasional racing.

There is, of course, the well worn expression (recounted to me perhaps a thousand times in the past few months) that the best two days of a boat owners life are the day he buys his boat and the day he sells it. I don’t know about the second part, but I do know about the first and once again conventional wisdom is, at least in my case, rubbish. I have done some ‘out there’ things in my life, but I can pretty much say that the first day of boat ownership for me was not the best day of my life: it was the scariest.
As I stepped on board for the first time as the owner of a big, expensive, and yes, beautiful new yacht, only one thought came to my mind: OH MY GOD…. WHAT HAVE I DONE???!!!! I was, without a doubt, totally overwhelmed and totally petrified. Suddenly it was all on the line: my commitment, my knowledge, my reputation, my money. All right there, sitting in the water. OH MY GOD!!!

For years I told anyone who cared to listen, “Yup, in a few years I’m gonna buy me a big sailboat and cruise around…. maybe even sail around the world!” I went to boat shows, subscribed to a bunch of sailing magazines and cut out ads for boats I wanted, cruised the docks whenever I had the chance, talked with experienced sailors and read endlessly about electric systems, sail plans, cockpit layouts, power options, communications and anything else even remotely associated with boats.

I was on my way to New Zealand to watch the America’s Cup races this winter when I happened across an ad in a boating magazine for the boat of my dreams. The boat, a 42’ Fountaine Pajot (French, of course) catamaran, was in San Diego. Since I had a short layover in L.A. before continuing to Auckland, I decided that a short detour to San Diego would make perfect sense. I landed in L.A., rented a car and drove down to Loews Coronado Bay Marina, a very posh resort/marina on San Diego Bay where I met the owner and had a quick tour of the boat. It was immaculate. It was also $60,000 more than I wanted to spend, and besides that, I was not totally ready to make the leap to major boat ownership yet. Still kicking tires.

The owner had worked as a programmer for Oracle for ten years. In 1990 when he started, the internet was just spooling up to light speed and the sky was the future. Within four years, with stock options and other perks, fresh out of college, he was a millionaire. That was only the beginning. He bought more stock, the company kept flying high, and by 2000 he was worth over $10 million. Life was good. He was spending $40,000 a month on, as he put it, stuff. Fancy clothes and cars and toys of all sorts, an expensive apartment and every meal at the best restaurants. And, in 1998, a brand spanking new $370,000 catamaran. Living large!

Then, as often times is the case, shit happened. His stock portfolio, like everyone else’s, tanked. Big time. Instead of bailing—or even saving a million or so “just in case”—he continued spending, refusing to believe that his life would, or could, ever change. Within three years the party was over. He was down to his last $100,000, an old van, and a beautiful boat which he was now living on.

He had the boat listed with a broker for many months, like so many others in his situation, refusing to believe that it wasn’t worth the $500,000 he had into it. By the time I met him it had been on the market for nine months and he told me that if he didn’t sell it in the next few weeks he was going to pack up and head to the South Pacific, which sounded very strange to me indeed. Sell it or go around the world? I thanked him for the tour, told him I’d think about it (but not at that price), and headed to New Zealand.

A week later I got an email from him asking if I was still interested. Yes, I reiterated (a large knot growing in my stomach at the mere thought of actually spending that much money….on a BOAT!), I was still thinking about it, but at a much lower price than what he wanted. I gave him a ball-park offer and told him to think it over.

A few days later he wrote back and said that he would consider my offer but he’d be taking some of the “stuff” off the boat at that price. No way, I said. I wanted ALL that cool stuff—radar, SSB and VHF radios, watermaker, washer/dryer, dinghy with outboard, dive gear, GPS, spinnaker, safety equipment, etc.—which he had spent tens of thousands of dollars on. Okay, he said, but only if we could do the deal quickly. I gulped. Hard. OH…MY…GOD! What was I thinking?

A boat? A BIG boat! A big EXPENSIVE boat! A big expensive boat berthed in a fancy expensive marina and ready to gobble up every penny I could throw at it. What WAS I thinking???