What ever possessed us to buy a boat, anyway?

Let me start by saying that Theresa and I aren't liveaboards, and we don't know if or when we'll ever adopt the liveaboard lifestyle. This gives our logs a somewhat different flavor from those on many of the other cruising websites maintained by dedicated liveaboards. Our cruising endeavors do, however, have their roots in the liveaboard dream.
I grew up in a family of sailing enthusiasts. My uncle Ernie got involved in sailing when he was young, and won lots of races in iceboats on the Great Lakes and Y-Flyers on the east coast. Eventually, he got his Coast Guard Captain's license, and spent several years as a freelance delivery captain, hanging around in Florida, the Bahamas, and the Virgin Islands.

My uncle's interest in sailing sparked an interest in his two brothers, and my parents joined Lake Norman Yacht Club northwest of Charlotte when I was still in grade school. The Lake Norman Yacht Club attracted some really good sailors, and it soon developed one of the best junior programs on the east coast. I went to sailing camp every summer, and was very active in junior racing for most of each year through junior-high. While still in high school, I raced Sunfish, Lasers, 420's, Hobies, Y-Flyers, and Thistles, taking trophies in most of them.

My sailing hobby hit the skids when I went off to college. Lake Norman was too far away to visit regularly, and I had to work in the summers anyway to pay for college. During some of this time, my uncle Ernie actually lived on a beautiful Swan in Baltimore Harbor, and he continued to talk about the trials and tribulations of the liveaboard lifestyle, both as it pertained to his current situation and to his earlier years in the Caribbean. Before I graduated, he abandoned the liveaboard life for a family and house in Fredricksburg.

As fate would have it, my first job out of college was in Baltimore at Alex Brown & Sons. Near the end of my first year there, one of the analysts (a young fellow named Chris Ruth) bought a decent-sized sailboat and announced that he was going to sail around the world. He had almost zero sailing experience, but his determination was unshakeable, and he was doing tons of research. I spent some time learning about his plans and his boat in the months just before his departure. I was inspired by his resolve. If he could do it with so little experience (and cash), surely I could do it with my sailing experience and a similar amount of cash!

By the time my first year's lease was up in Baltimore, I was completely enamored of the liveaboard dream. Work at Alex Brown was incredibly stressful; I was on call every other week, 24x7, and I regularly worked 70-hour weeks with occasional 100-hour weeks. The liveaboard lifestyle represented a means of escape from this workaholic existance. I started seriously researching the notion of buying a sailboat as my primary residence. I didn't have a lot of money, but as a computer guy, I needed a decent amount of space. After several weeks of searching, I put an offer down on a beat-up 46-foot Morgan, but I couldn't get financing, and the deal fell through. Three months later, I got a job offer in St. Louis and moved out to the Midwest (where no one really sails anyway).

I lived in St. Louis for a year and a half, and only managed to sail once the entire time (on a Sunfish at the beach). I met my future wife in St. Louis, and in 1995, we moved back east to Alexandria, VA, where I started a company called Interactive Financial Services with the help of some friends. We were bought out a year later by Intuit (the makers of Quicken and TurboTax) for a sizeable amount of Intuit stock.

I had talked with Theresa about my dream of buying a sailboat, and now that we both lived near water and had the money, I was excited to act on it. We went shopping for the "perfect" sailboat in the summer of 1996, and we found it pretty quickly: a beautiful Swan 46. We were sitting on the boat with our broker, listening to the rain patter on the deck, when I suddenly realized that it wasn't really the boat that I wanted, but the lifestyle that I associated with it... and that the lifestyle was quite a bit costlier than the boat!

Unfortunately, Intuit's stock was in a steady decline that took it from $54/share to less than $18/share. I wasn't willing to sell it at such a deflated value, so I worked at Intuit for another 2 1/2 years -- hoarding cash and waiting for Intuit's stock to recover -- but all the time growing more and more dissatisfied with the whole "work thing". (Starting and growing a company is a lot of work, and an Internet startup is like a 300-pound monkey on your back, pounding espresso as fast as you can brew it!)

Theresa and I got married in September 1998, and by January 1999, Intuit's stock had recovered and most of my options had vested, so I quit. By this time, I was more focused on improving my lifestyle than pursuing the liveaboard dream, per se. I soon got involved part-time with another Internet startup, and Theresa continued to work, but under increasingly adverse conditions. By the summer, she was ready to quit too.

Sometime in May 1999, I got a call from a friend of mine in Hong Kong regarding a job opportunity there. Theresa and I flew to Hong Kong, where I interviewed for and landed the most lucrative offer of my life. This posed a major dilemna: If I were going to work, this was definitely the best job offer I was going to get. But did I quit Intuit just to take another job? Theresa and I talked about what we wanted to do with our lives, and decided that this would probably be the best -- and perhaps only -- time to pursue the liveaboard dream. Theresa had even begun to buy into the notion that it might be fun to take a break from work and sail about the world for a few years, even if it meant being "stuck on a boat in the middle of the ocean" with me. Theresa's only wish was that we could make her dream trip to Italy before we moved onto the boat, so we agreed to plan a trip for September 1999, to correspond with our one-year anniversary.

We started looking for a sailboat in June 1999 -- a used boat in the 44'-46' range, with shallow draft (to get into shallow harbors), but with good performance characteristics (so we don't wallow into every harbor like a pregnant sow). We planned to buy the boat sometime that month, and to take until October to get her outfitted. We intended to put most of our stuff in a storage warehouse in Annapolis, sell our townhouse in Alexandria, and move onto the boat. We planned to sail south along the US coast in October, taking it easy and learning how to handle the boat. We intended to explore the Florida/Bahamas area until January 2001, then sail south, through the Panama Canal, and over to the Galapagos. After that, we considered heading back north up the US coast, and spending the summer in Maine, Nova Scotia, and Newfoundland before heading east across the Atlantic to the Mediterranean.

At least, that was the plan...

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