Sailing Off Into the Sunset 

The Ups and Downs of Becoming a Liveaboard Cruiser 

I didn't wake up one day and say, "I'm going to be a liveaboard cruiser." Instead, I entered the lifestyle in phases, over the course of nearly a decade. The process involved a certain amount of luck—it just as easily might never have happened. It also required so much work and so many lifestyle changes that I'm amazed I pulled it off. But looking back five years later, I can say it was well worth the effort.

First Taste of Cruising

My first taste of cruising was in the spring of 1989 when I crewed aboard a friend's boat in Mexico. I spent a two-week vacation aboard the small Hunter sailboat, cruising up the Baja coast on the Sea of Cortez. It reminded me a lot of camping, since we didn't have all the comforts of home and we spent a lot of time outdoors (we also spent a lot of time trying to fix the engine). I liked the adventure of seeing new things every day, of being close to nature, and the challenge of traveling by boat. Living on the boat was a great stress-reducer, and I pretty much forgot about the outside world. When my vacation ended and I returned to the "real world," life was quite jarring and fast-paced until I re-adapted.

I enjoyed my first cruising experience, but for the time being, I just mentally filed it away as an interesting diversion. My lifestyle revolved around my job: computer software design. I liked working with computers, and I was good at it. My career was advancing, and I was making plenty of bucks. Plus, I already had all kinds of hobbies, and didn't need another one.

Starting to Dream

Fast-forward a few years: I was caught up in the rat race. The computer projects were getting bigger and the schedules were getting tighter. A few things came together at this point to get me thinking about the possibilities of buying a boat and going cruising. I had a stressful job and had an unhappy end to a house-building project. I also turned 40 years old, and had a bit of a mid-life crisis: Did I want to spend the rest of my life sitting behind a desk pounding out computer code? Where was the adventure in my life? I started to think about doing something else. I had some money in the bank, and had a modest paid-for house as equity. I started to dream.

To feed my dream, I subscribed to sailing and cruising magazines and strip-mined the library and used-bookstores for cruising books. I read to acquire "book learning" about technical details, and to vicariously experience other people's adventures. During this phase, I spent a lot of time staring at tiny photographs in the boats-for-sale listings, thinking about what it would be like to own this boat or that boat. But so far, it was just book learning, vicarious experience, and dreaming. But I was still interested.

Getting Real

By the mid-90's, I had been dreaming for a few years, and it wasn't getting me anywhere. I decided to take some active steps to make things happen. I started going to boat shows, not to buy, but to look at real boats and study their gear and accommodations. Also, I have not been a lifelong sailor, and didn't know much about it (other than being good crew by doing what I was told). In August of 1995, I took a beginning sailing course to learn the basics. It was too short to help much, but I enjoyed getting out on the water. I needed a more formal cruising experience, especially on a bigger boat to see if I could handle it. I also needed to make sure cruising still had a powerful appeal.

In April of 1996, I took a liveaboard cruising course at Offshore Sailing School. This was my biggest cruising adventure so far. The course was held at the Moorings charter base at Marigot Bay, St. Lucia, so it required travel to an exotic location (which added some spice). For a week, we cruised around St. Lucia and Martinique on a 45-foot Beneteau, anchoring out and visiting the shoreside towns. The course instructor was an old hand at sailing and cruising, and was an excellent teacher. I thought the whole adventure was terrific, plus I learned a lot through first-hand experience. I came away convinced that I could handle a bigger boat and that I would enjoy the cruising lifestyle. In retrospect, of course, I only experienced the "fun" side of cruising—later on I would encounter other less enjoyable sides of cruising.

Going For It

[Sailboat masts at marina]  
"Do you think they take sailing seriously here?" A forest of sailboat masts crowds Bert Jabin's Yacht Yard, Annapolis, and the waters of Back Creek, beyond.  

Now that I had decided to go cruising, I had to disentangle myself from my shoreside existence. It took a year to wrap up various commitments, then in November 1997, I quit my job as a computer engineer. I thought that transitioning to cruising would be a full-time job in itself. If I still held a "day job," I was afraid it would take so long to transition to cruising that I might never get there. I also worried that as long as I had a comfortable and reassuring income stream, it would be very hard to break all ties and sail off into the sunset. I told my coworkers I would be living on a boat and going cruising, although in truth I still didn't know if it would all work out. I also started educating my mother. She was worried that this whole boat thing would be dangerous—why was I quitting a good job to sail off into the unknown?

Luckily, I lived only 90 minutes from one of the biggest concentrations of sailboats in the country: Annapolis, Maryland. I wrote up a set of boat requirements, engaged a broker, and started looking at boats. The broker did a good job of filtering the computerized listings and only showed me boats that were real possibilities. I looked at maybe a dozen boats, and wound up buying one in January 1998. It was actually the second boat I looked at, a 1982 Fast Passage 39 cutter. I liked it as soon as I saw it, and it felt like home as soon as I went aboard.

The survey found a few problems that had to be corrected, so I made up a schedule that went like this: Do all the repairs and refitting in the spring of 1998, take a Chesapeake Bay shakedown cruise in the summer, then leave for Florida in the fall. Well, I did leave for Florida in the fall, but instead of fall 1998, it was fall 1999. In retrospect, my refitting schedule was wildly optimistic. I recently looked at it again, and it was hilarious. Things that wound up taking a week, I had scheduled for a morning, with some other refitting project in the afternoon!

On the positive side, I am a dedicated do-it-yourselfer. I love poring over gear catalogs to pick out equipment and supplies. I am good with technical details, and did a good job planning and executing the various refitting projects. Plus, I have eight toolboxes full of tools, and am quite competent using them.

Hitting the Wall

But I wasn't prepared for the magnitude of the job! In my book learning, I had read about people spending spectacular amounts of time and money refitting a boat, and I remember being puzzled. How was it possible to spend so much time and money on a presumably straightforward possession? Well, now I was finding out that refitting a cruising sailboat is anything but straightforward.

First of all, a boat is not like a house. I had done lots of work on my house, including finishing off the basement and remodeling the main floor. House work is relatively simple. You usually have lots of space in which to work, and the materials and tools are widely available, easy to use, and relatively inexpensive. By comparison, boatwork can be downright ornery. You have to work in cramped odd-shaped quarters, sometimes suffering pain and bruises. Materials and tools are frequently hard to find and very expensive.

To get an idea what boat work is like, imagine doing extensive equipment installation and repair with wiring, plumbing, and carpentry, inside a small odd-shaped kitchen cabinet in your house. Imagine rebuilding your bathroom, but first shrink it down to the size of a phone booth. Imagine working on your car's engine with the hood closed, by removing the grille and radiator and crawling in through the front. Then there was the neverending-ness of it all. I completely filled one notebook with diagrams of AC and DC wiring, plumbing and hoses (for five water systems plus fuel and propane), standing rigging, running rigging, steering, ground tackle, refrigeration, engine and propulsion, dinghy and outboard, hardware and brackets, gizmos and gadgets, ad infinitum. As a former computer engineer, I like technical details, and I like everything to be "just so." But when I printed out my big to-do list for the boat, it was 31 pages long! My initial joy and optimism gave way to frustration and disillusionment—the honeymoon with the boat was over.

After months of work, I had barely made a dent in the huge to-do list. I found more work everywhere I looked, and new items got added to the list almost as fast as old items were crossed-off. Time was flying and my cruising funds were dwindling, yet there was no end in sight. I reached a low point filled with anguish and extreme frustration.

Initially I thought I would do boat work to the exclusion of all else; I abandoned other hobbies and activities. That way, I reasoned, I would get "done" as soon as possible. But I discovered something that every other boat owner has discovered: the boat work is never done! Maintaining and upgrading a cruising sailboat is a never-ending process. I also came to realize I couldn't do boat work exclusively—that's a recipe for burnout in any discipline. I wound up re-prioritizing tasks and reducing the workload. All nonessential items would have to be deferred, but at least I would have a life besides boat, boat, boat.

The Pieces Come Together

[Bridges on the Elizabeth River]  
Looking aft just after passing under the Jordan Lift Bridge on the Elizabeth River in Norfolk, VA.  

In the fall of 1998, I fixed up my house and sold it, moving on to the boat full-time. With only one residence occupying my time and with a stripped-down to-do list, progress was much more apparent. I worked through the winter and into the summer: rebuild the propane system, build shelves, install a regulation bell, rig up a bilge high-water alarm, do woodworking and wiring for the stereo system, rebuild the toilet and the waste system, replace the broken traveler, install safety pad eyes on-deck, service and repair the Max-Prop, improve the topping lift, install the GPS, service the seacocks, service the winches, grind out blisters and paint the bottom, install new electronics and wiring (charger, regulator, energy monitor), repack the stuffing box. Each item became a separate little project, and I became very good at multi-tasking—designing project "A" while waiting for parts for project "B", interleaved with installing gear for project "C" and finishing-up project "D".

In late summer, I reached a major milestone: after a year and a half of work, the boat was finally "ready." I checked-out of the Annapolis marina and went on a planned shakedown cruise on Chesapeake Bay. It was an enjoyable cruise and I learned a lot every day, but I discovered more problems right away. I added a dozen problems to the list; the worst ones: the house bank batteries were shot, the depth sounder barely worked, and the new anchor rodes overfilled the chain locker and jammed the windlass. I also ran into trouble with a couple of guys named Dennis and Floyd—a pair of hurricanes that blew through the area.

The shakedown cruise was a valuable experience, but as a novice cruiser traveling by myself, I found it to be stressful. To be sure, the hurricanes generated a lot of anxiety, but my lack of experience caused additional stress, plus there were the boat problems. I went back into the marina to rework the boat and rethink my plans.

After reading so many exciting cruising tales, I had become attached to the concept of single-handed sailing. But after experiencing it first-hand, stripped of its romance, I came to realize that it was more than I could handle. At my current experience level, single-handing was just too much work and too risky. I decided I needed a crewperson, so I posted a crew notice on the marina bulletin board. A few days later, I got a phone call from Brent, a power-boater who said he was interested. We got together and went over the details, and it looked like a good match—I might actually have crew!

After six more weeks of boat work, the boat was as ready as it would ever get. Brent, my crewperson, had signed-up to go. I had charts, provisions, spare parts, an envelope full of expense money, and a good weather window. All the pieces were in place; it was finally time to go cruising!

[Locking through at Great Bridge, VA]   [Motoring down the ICW]
Locking-through at Great Bridge. My crewperson Brent tends Sunspot's lines as we transit the U.S. Army Corps of Engineers lock at Great Bridge, VA.   Motoring down the ICW through a cypress swamp, on the Alligator River - Pungo River Canal in North Carolina.

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