Shopping for a Boat

A journey along the Eastern Seaboard looking for the perfect sailboat

Inspired to write after selling the farm in 2022, I headed to California for a retreat. I also started looking for properties online as I was still itching to initiate another land-based community project.

I logged into Yacht World one day, out of curiosity, and immediately got transfixed by sailboats, and how much my money could buy. I did not indulge for too long, not wanting to get distracted, or caught in a fantasy. Strangely, ever since I stopped commercial fishing in 1988, I never thought of going back to sea, my five years on the ocean having somehow cured my dreams of sailing the world.

Back in Santa Fe a couple months later, with no inspiration on my radar, I caught the boat fever again, some of it prompted by a friend refitting his sailboat in New Orleans. I started researching about affordable ocean-capable boats, took copious notes, and soon was headed to Louisiana to help my friend get his boat ready.

After working for a few days in the overwhelming humidity of the gulf coast, I began my boat search, driving through Mississippi, Alabama and then Florida. Having never visited the gulf coast, I relished some of the old marinas and pristine white beaches until I reached the Sunshine State, which was a bit difficult for me to bare. Being the bohemian that I am, traveling in a 1999 Tacoma with a camper top, I felt quite out of place, as well as out of fashion!

My morning routine consisted of researching boat listings in the area, checking their reputation and known issues, and making appointments with brokers. I soon identified boats between thirty and forty feet that fitted my budget and needs.

Sailboat Data lists the characteristics of production sailboats; displacement (weight), draft, capsize coefficient, hull speed, sail surface, engine type that the boats originally came with, water, fuel and waste water capacity, comfort ratio, production years and number of hulls made.

After looking at a few boats in Tampa and St. Petersburg, I visited my first boatyard in Placida. During Hurricane Ian, many boats that were stored there fell over, and people were busy repairing the damage.

I crossed over to Lake Okeechobee to visit the Indiantown Marina where a couple hundred boats were on the hard, some being worked on, or stored during the off season, and others just weathering away, seemingly abandoned by their owners, whose passion to be at sea, or financial fortune, had faded away.

I started to get familiarized with the different brands of boats, and quickly discovered how friendly the boating community was, people often willing to share their knowledge and experience.

Driving all the way to the northern part of Maine, I stopped at every boatyard I could find. Some of them, like Bert Jarbin Yacht Yard, or Herrington Harbor near Annapolis, Maryland, cover dozens of acres. Besides looking at boats within my budget, I also got to see outrageous multi-million dollars super yachts.

My boat search yielded some interesting encounters. In Florida, I befriended a long-time captain who worked for the UN, and owned a sixty foot ketch. I stayed in touch with him along my journey, often asking his opinion regarding boats I was interested in.

In Beaufort, South Carolina, I met an older Danish seaman fixing his boat. A friendly and talkative fellow, I though I would pick his brain and invited him to dinner. He showed up drunk, was obnoxious with the waitress, and talked nonstop about his days in the merchant marine. In kind of a sneaky way, he offered to sell me his boat for an amount within my budget. That was, after telling me in the morning that he was planning to cross the Atlantic, and cruise the Mediterranean once his boat was finished! Curious to check the configuration of his classic Southern Cross 35, I visited his boat the next day. It was a mess and the fellow was disappointed that I wasn’t naive enough to fall for his offer!

In Deltaville, a lovely boat haven located on the Chesapeake Bay, forty miles from the Atlantic Ocean, I looked at a Pearson 40, also known as the Whale Body, designed by naval architect William Shaw, a centerboard boat well suited for the Bahamas with its shallow draft.

The boat was in extraordinary shape and was loaded with tons of equipment like a life raft, watermaker, diesel generator, new sails and more. I was very impressed and, of course, very tempted! Compared to other boats I had so far looked at, it was a lot for forty thousand dollars! I read a favorable review in Sailing Magazine, by famed sailor and writer John Kretschmer, and spent two more days in Deltaville, doing further research. After speaking with the owner again, he confessed that it was the perfect Bahamas’ boat, but not the best for sailing around the world. I had money burning a hole in my pocket and was eager to buy a boat, so my two days checking that Pearson were a bit torturous.

At the same marina, I met a young woman who had bought a Fast Passage 39. While sailing the Chesapeake Bay, she experienced engine trouble and hauled out the boat for repairs. She went back to California for work, and during her absence, the cockpit drains got clogged by leaves, resulting in rains flooding the cabin, ruining the wood work and electrical wiring. She had been rebuilding the damaged interior for the past three years and, when I visited her upon my return from Maine a month later, she had pulled the engine out, and was rebuilding it, with new pistons, rings, valves and crankshaft. I was blown away by her determination to rebuild her boat.

In New Jersey, I looked at a Contest 36 that was on my list since I left Santa Fe. A one owner, immaculately maintained vessel, I got very close to making an offer, but got cold feet because the boat needed new sails and navigation instruments, and the engine needed to be rebuilt.

It’s easy to get mesmerized by the beauty of a boat that forty-thousand dollars can buy, but it’s humbling to learn how much it takes to refit it before undertaking any long passage. A boat must be hauled out at a yard for weeks or months, while everything gets checked, repaired or replaced; engine, standing rigging (cables holding the mast), running rigging (ropes to trim sails), chainplates (the steel plates joining the standing rigging to the hull), rudder, etc. In most older boats, navigation instruments should be upgraded, as well as sails and electrical wiring replaced.

In essence, it is not uncommon to spend twenty to thirty-thousand dollars on a refit after purchasing a thirty year-old boat for forty-thousand dollars. Without refitting a boat, one risks to encounter serious breakdowns during rough seas. Loosing engine power, dismasting, or an electrical failure near shore is dramatic enough, but when it happens on the open ocean, it can be catastrophic.

From knowing very little about sailboats, I began an education into which boats I should look at, what to check when inspecting a boat, and what questions to ask. Unfortunately, yacht brokers, just like car salespeople, usually know very little about a boat’s history, I found out. Even when speaking with boat owners, I was often leery of their answers regarding engine hours and rigging maintenance.

I came close to buying a boat a few times, with reputable brands like Cape Dorie, Contesa, Seasprite, Hallberg-Rassy, Tayana and Contest.

All along that journey, I kept imagining myself on a thirty-five foot boat. What would I do all day? Visit exotic places? Knowing how I’ve never liked being a tourist, I began questioning my desire to buy a boat. Was I trying to escape the land of enchantment (they call it the land of entrapment), feeling like my time in New Mexico had come to an end?

Upon returning to Florida, where I had planned to visit a few more boats, my intuition told me that I wasn’t ready to buy a sailboat. That maybe, I should go cruising on other people’s boat for a while, and discover whether boat life was really for me.

So I beelined from Jacksonville to Santa Fe.

That two-months, eleven-hundred miles journey was just the beginning of a deep dive into the cruising world. Back in Santa Fe, I signed up on a crew finder website, and within a month, received an offer to sail from Seattle to Los Angeles on a beautiful yacht. I’ve now logged over 6,000 miles on four different boats, recently sailing from Panama to French Polynesia, then Fiji, and I will soon be heading to New Zealand.

I’ve been lucky to find crew positions, some of them paid, on gorgeous boats, with great captains and crew mates. It’s given me a good taste of boat life, including cruising with young kids for three months, staying at fun marinas and quaint tropical anchorages, and doing long passages. The boats I’ve crewed on have been in the fifty to sixty-foot range, and quite luxurious. Needless to say that I’ve been getting a bit spoiled!

I’m really glad I did not buy a boat! This boat search, and cruising the South Pacific for six months, has confirmed what everyone says-sailing is an expensive hobby!

For the time being, I will most likely continue to seek crew positions on interesting boats, while also doing work trades in far away places, like I have been doing in Tahiti, Huahine and Fiji. During these stays on land, mingling with the local population, I let myself be inspired by a different way of life.

Sometimes, I long for a homestead, where I can have a garden and animals, and be able to sleep in my own bed.

Nothing wrong with dreaming, right?