I’ve owned six boats in the past 40 years. I’ve cruised and raced them, crewed in countless regattas on other people’s boats and more. I can and do talk boats forever. I love them all: sail and power, dinghies and superyachts.
So, people often ask me what type of boat they should buy. My unequivocally firm answer is that you should buy the boat you can afford. And by “afford,” I do not mean the biggest boat that you have enough cash on hand to purchase. I mean the boat that you can afford to purchase and then properly maintain, without being shocked by the size of the invoices from the boat yard.
“If you buy a used boat in anything less than showroom condition, count on 15 to 20 percent of the purchase price annually for at least three years,” says David Doody, general manager of Safe Harbor Capri in Port Washington, New York. “After that, it could be between 10 and 15 percent. If you can’t afford it, buy a less-expensive boat.”

Far too many people fail to realize just how big of a maintenance budget needs to be factored into any purchase decision, Doody says. “When we send a yearly yard bill, they are shocked. A $400,000 fishing boat can easily have a yard bill of $40,000,” he says. “Things break, systems need replacing, electronics go bad. Sometimes it is even a safety issue. The last thing you want to do is head out with compromised engines or propulsion.
And the reality is that unless you’re willing to pay top dollar, you’re likely going to be buying a boat that needs work. Finding a reasonably priced option on the brokerage market that’s in showroom condition can be challenging, as I learned a year ago while trying to help my brother and his 20-year-old son upgrade from a 22-foot Catalina to something in the 28- to 30-foot range. Their price range was $14,000 to $23,000. The search with that pricing parameter was downright depressing. The majority of boats we looked at were not just neglected, they had been abused. If they had been animals, someone would have called the ASPCA.
We saw boats that had been left to fend for themselves every winter, pulled from the water and uncovered, leading to cracked fiberglass decks, portlights crazed and leaking, wood trim checked and split, canvas faded and rotted, stained exterior cabin sides, hatch lenses smoky and opaque.
We saw pitted standing aluminum rigging, unpainted masts and booms, worn and tired running rigging, and shafts and props that looked like they would have to do battle just to turn. Unvarnished cabin soles were gray and brittle. Accent trim was left to fade. Cushions were faded and stained. The bedding looked as inviting as a fleabag hotel’s.
None of these boat owners could afford the boats they purchased, at least not when “afford” includes regular maintenance and occasional upgrades.
I own a 1993 Sabre 38 sloop called Sachem, which I purchased 15 years ago. My yard bills are equal to the cost of an annual state college education. I can afford that expense to keep her in good condition. What I can’t afford would be to keep a 70-footer in good condition. I accept my financial limitations, and I focus on making the boat I can afford the best that she can be.

Over the years, I have redone everything on Sachem. She got new hull paint; received new canvas (twice); had her underbody sanded down and new barrier coatings applied. I wooded all the exterior brightwork and revarnished it; installed new hatches and portlights; completed an interior refurbish of all the wood surfaces including the cabin sole; upgraded all the electronics and added an interior GPS monitor, as well as a VHF radio with AIS; and refurbished the interior cushions with new foam. I also had to replace the rudder and rudder post; that alone was an $11,000 expense.
Yearly motor, shaft and prop maintenance is on a carte blanche basis. If the yard’s mechanics even think it is worn or could be less than perfect, it is replaced. The last thing I want is to be cruising offshore when something breaks that was flagged as iffy.
My brother and nephew took my advice about the true meaning of “affordable.” In the end, they chose a vintage Pearson 303 sloop. She was in near-perfect condition. The spars were painted, the gelcoat gleamed, the canvas was good enough, and the interior was even better than new, as the owner was a carpenter and customized it. Only the sails needed to be replaced.
The boat was at the high end of their price range, compared to others they considered, but they would save way more than $10,000 by not having to repair and replace everything on board. Their desired upgrades could be done over a few years.
My brother and nephew now have a proper little yacht they can be really proud of, and one they can really afford to care for properly.
This article was originally published in the September 2021 issue.