The journey begins: Persistence, my 1985 Gozzard 36 Pilot House

Introducing Persistence, nee Dream Catcher, the base of the next big phase of my world travels.

It has now been over 20 years since I first put to sea on the Pacific Ocean, which I crossed in an aircraft carrier, USS Ronald Reagan. I only “lasted” a single deployment, but in that cruise of a little over six months, I got to “see the world” in the form of crossing two oceans, the Equator and the International Date Line, visiting half a dozen foreign ports in Australia, Oceana, and Asia, and ultimately, including my road travel, passing through 17 out of 24 nautical time zones.

When I returned from that trip, it occurred to me that I had a good start on a handful of travel checklists. I did not want to immediately go on traveling just as an end in itself, as I had other concerns at the moment, but when I returned to San Diego and it was time to drive back to New York, I made the simple choice to alter my return route to go through more unique States than necessary. Having crossed westbound through only the “border” states – down the coast to Georgia, then Alabama, Mississippi, Louisiana, Texas, NM, AZ, CA – I decided to “bump up one state” and cross through Utah, Colorado, Kansas, etc on my way home, so that by the time I was back from that journey, I had visited more than half of the 50 states. Then in summer 2007, an old friend convinced me to take a road trip through eastern Canada, “covering” not just half a dozen provinces but also getting one more time zone, putting me at the current 17 time zone count.

By the time of that 2007 trip, I already knew that I was heading pretty intentionally toward a career in law, but I wanted to make sure my travel opportunities didn’t stop. In 2008, I managed, mostly by happenstance, to find a legal job that would “require” (allow, in my head) a lot of travel, and ultimately that job, which transcended law school and existed for me both as an “advanced paralegal” and a licensed attorney, got me to not just visit but work in well over 30 states, getting my state count to 43 before the pandemic ended the mandatory travel aspect of the job. In 2023, I manually finished the “50 state project” by driving my Volvo to Alaska, and now, well, the itch is still there. It’s time to travel again, it’s time to do something new again.

A small part of me feels like I used the 50 state project as an excuse to stay stagnant. From 2007 to 2017, I allowed my passport to expire without a single stamp in it, and even waited a few years to renew it. I still have a pristine book that hasn’t even been shown at the Canadian border. That feels like a personal failure. I want to finish something that I started. What, exactly? Well, let’s start with the oceans. At this point I have crossed two oceans, and visited three. I chose not to visit the Arctic in 2023 in part to “save something big for next time.” So now it stays on the list. I’m not planning to ever “cross” the Arctic or Southern oceans, but yes, I will need to navigate upon them in some fashion at some point. What I do want to accomplish is complete, though across more than 20 years, the “simple circumnavigation.” This means traversing a complete closed loop around the planet, a loop that at some point touches itself. To accomplish this, I basically need to return in some fashion to the Straits of Hormuz, as everything beyond that last time was “a dead end” from which one has no choice but to backtrack unless changing modes from sea to air.

So, there’s a concrete geographic goal here: to finish out the circular path that began in New York, changed from land to sea in San Diego, and terminated at sea in the Persian Gulf. To do that, I need to cover, somehow by land and sea, a path that goes from New York to the Persian Gulf itself.

This journey can be and is routinely completed in a handful of ways, most of which involve oil tankers. I had considered that option: to crew on a tanker or other cargo ship, or even a series of them, to make my way across the Atlantic, and then either through the Med and the Red to get to the Indian Ocean again, or around the Cape of Good Hope the long way and then back up along the eastern coast of Africa to the Middle East again. But, I can’t crew on a cargo ship and still remain focused on other priorities and goals. I have my dog to consider. I have my legal career, which I can work remotely and part-time, but cannot abandon entirely. These and other factors lead me to “it has to be on my own boat,” and both the cost of fuel for such a journey and the environmental considerations mean that a sailboat is really the only practical and suitable option.

The timing is based on a few things but the main two are this: the resolution of my father’s estate, giving me not a fortune but a small amount of financial breathing room, and the fact that, heading into my 45th birthday, I am no closer to, in fact further from, my goal of becoming a father, when compared to twenty years ago. This is either the ultimate expression of freedom for a childless person, or a bet the farm Hail Mary way to give the universe one last chance to connect me with the right partner.

So that’s why I bought a boat.

Why this boat?

Based on the known goals, I knew that I needed a boat that was suitable for extended ocean travel and robust enough for a possible North Atlantic crossing, often described as one of the most challenging passages for a sailboat. I talked to a lot of people and there were some consensus ideas:

• Get something with a full keel, or at least a “modified” full keel for stability and tracking in heavy seas
• Get something practically bulletproof in materials, design, and construction technique
• Spend less on the boat itself to leave more in the budget for refitting to suit my goals
• Get something soon so that I can start preparation in advance of finishing the estate process and getting the business to a good spot for a break

So, it ultimately came down to, now is the time. What, where, and how remained to be figured out in the usual fashion. In early October, I started calling around to set up sailing classes, something I would have done much earlier if finances hadn’t been uncomfortable for most of 2024 and 2025. It turned out there was a “101/103” class being offered that very weekend, so I gave them my credit card and packed the car for the five day class in Annapolis. Visiting Annapolis for the second time was a whole other story in itself, but along the way I met a yacht broker, because she just happened to be the instructor of the class. During our second day of sailing, a small fitting that served an important role on the boat broke, which led me to a bit of an infodump explaining to the instructor how I would respond to a problem like that on my own boat. I could see that old “light bulb” expression on the instructor’s face, and she said “I think I have the boat for you.”

She told me about this old Gozzard that she “rescued from sinking.” It was an interesting old boat with a classic “pirate ship” design but a few years of neglect. It was built heavy, overbuilt really, as many early fiberglass layups were, and was designed for ocean cruising in comfort. But it was an estate sale situation, with an owner who had become disabled due to an unfortunate geriatric health condition, and the boat was in bad enough shape that most brokers refused it and the family was looking to just get rid of it. I went back a few weeks after the class to take a look and it was kind of like love at first sight. It reminded me of how I felt when I met Jackson and knew right away that he was “my dog.” I made an offer for about half what I was told they were asking, and it was accepted quickly. I then had a survey done, a bit of a story in itself, and the survey found what I expected: a handful of pretty minor problems that were all within the realm of “deferred maintenance” but nothing that would prevent the boat from being seaworthy at least for coastal cruising, and yet a long enough list of minor repairs to get the appropriate value very close to zero. I rounded up to a figure I felt would at least cover the expenses of sale and leave the family without taking an immediate loss on disposal, and they accepted. So now it’s mine.

This is already a pretty lengthy post, but it’s kind of a catch up as I haven’t been writing here about this particular journey yet. If you’re reading this later on, it may look excessive after I circle back and move posts here from Facebook retelling other pieces of the story.

I’m going to create a new section of this site and it’s quite possible I’ll add a whole new site just for the sailing blog. But stay tuned as any of that will all be posted here first.