There’s an old saying among sailors: “The two happiest days in a boat owner’s life are the day they buy their boat and the day they sell it.” While my husband, Chris, and I can confirm the unbridled joy of buying our beloved 1979 Cheoy Lee 41, Avocet, we’re not quite ready to test the second half of that theory. After years of pouring sweat, love and bottom paint into her, we’ve promised to keep her for the long haul.
That said, we’ve been crew on the emotional roller coaster of friends preparing to sell their boats. Trust me: It’s a ride with plenty of ups, downs and the occasional splash of regret.
To demystify the process and help sailors prepare for what can feel like the nautical equivalent of sending your child off to college, I turned to two experts: yacht broker and sailor Josh Hannigan, as well as our pal and long-range cruiser Peter Metcalfe. They shared their wisdom, and a healthy dose of reality, on how to sell your boat while (mostly) keeping your sanity.
The Right Timing
Let’s rip off the bandage: The right time is now. “If you’re ready to let go, just do it,” Hannigan says. “Boats aren’t like real estate. They’re not investments that appreciate. Every day your boat isn’t on the market is a day the perfect buyer isn’t seeing it.”
Hannigan is more than a longtime yacht broker. He’s also a captain involved with yacht surveying, sailing instruction, and providing specialized services for watermaker systems and custom sails. He offers insights as an active sailor, instructor and liveaboard boat owner. He’s also an associate surveyor with the Society of Accredited Marine Surveyors and an instructor with NauticEd, making him a trusted adviser on boat ownership, maintenance and sales.
For Hannigan, boats are less like houses and more like relationships: There’s someone out there who will love your boat just as much as you do. But timing, he says, is everything: “The right buyer might be waiting for a promotion, selling their property or finally retiring. If your boat is out there when they’re looking—and it’s the best option—it’s game on.”
The trick, as with most relationships, is patience. Boats can take time to sell, and the seasons of the sailing world often dictate when interest peaks. But Hannigan says a well-prepared boat can sell at any time of year, provided it’s priced competitively and presented at its best.
First Impressions
If you’re picturing buyers strolling onto your boat and falling in love at first sight, you’d better make sure it’s worth swooning over.
“Think of it like staging a home,” says Metcalfe, who is in the process of selling his boat, the 38-foot Hans Christian Kessel, after completing a singlehanded voyage across the Pacific. “A clean, fresh-smelling boat with shiny brightwork makes it easy for buyers to imagine themselves living their dream on board.”
To prepare Kessel, Metcalfe embarked on a top-to-bottom makeover. “I revarnished the cabin sole, repainted the interior, refinished the teak, and even spruced up the deck paint. It was a labor of love—and a little heartbreak—but it made all the difference.”
Hannigan agrees, but with a sharper edge: “Every scratch, chip and stain is a negotiation chip that you don’t want to hand over. Fix it now, or be prepared to lose money later.”
His advice? Paint the bilge, tighten the hose clamps, and make the engine shine like you’re prepping it for a yacht show. “Every small detail adds up to one big impression: This boat is cared for,” he says. “Buyers can sniff out neglect faster than you can say ‘osmosis blister.’”
Keep It Functional
Boats are also like pets: They don’t do well sitting idle. Hannigan says systems left untouched for months will almost certainly revolt when you need them most. “Flush the heads, check the furlers, and make sure your wind instruments actually display wind,” he says. “Buyers will forgive quirks, but they won’t forgive neglect.”
Metcalfe adds that honesty goes a long way: “If you can’t fix every issue, be upfront about it. Disclosing known problems shows you know your boat and aren’t trying to pull a fast one. Buyers appreciate transparency, and it builds trust.”
I remember when we were buying Avocet. She wasn’t neglected, but she was definitely left untouched for months because the seller was in poor health. Luckily, we had a survey to support our concerns and could whittle the price down to a number that reflected the state she was in.
The Right Price
Hannigan’s pricing philosophy is refreshingly straightforward: Price your boat fairly based on its condition and market comps.
“Set a no-nonsense price that reflects a boat in good working order,” he says. “If everything works, buyers will pay for their preferences rather than penalizing you for deferred maintenance.”
The Broker
Selling privately can save you brokerage fees, but the process is not for everyone. Hannigan recommends asking, “Do I have the time, patience and knowledge to handle this myself?”
A broker can take care of marketing, showings and paperwork, making the process smoother—especially if you’re emotionally attached to your boat. (And let’s face it, who isn’t?)
When choosing a broker, Metcalfe suggests going with your gut. Ask yourself: Would I buy a boat from this person? “If the answer is no, keep looking,” he says. “A good broker should be approachable, knowledgeable and genuinely interested in finding the right buyer for your boat, not just making a quick sale.”
Patience Is a Virtue
Selling a boat takes time. Hannigan likens it to getting out of a gang: “It’s not going to be easy, and it’s not going to be quick.”
When it came to buying a boat, Chris and I took a whole year and put in two offers on two boats before Avocet fell into our laps. It took time, heartbreak and research to find the right boat. I can only imagine how Avocet’s sellers felt with the boat sitting on their hands for twice that amount of time.
Budget for the time it takes to sell your boat and for the expenses involved in keeping it in show-ready condition. Whether it’s in a slip or dry storage, a well-maintained boat is far more likely to attract buyers than one that looks like it’s been left to fend for itself.
Moving On
For Metcalfe, selling Kessel is bittersweet. “This boat carried me through some of my toughest times, but life has seasons. It’s time for me to move on.”
He expects tears when he hands over the keys, but also joy, knowing that the boat he loved is ready for its next adventure. We can’t wait to buddy-boat with him again someday. We are confident he will be on the buyer’s side of thingssoon.
What he’s going through right now, though, is what so many sailors endure. It’s more than a transaction. It’s a rite of passage. Whether your boat has been a faithful partner, a dream realized or a character-building challenge, preparing it for sale is your chance to honor its story while helping a new owner begin theirs.
So, give it your best. Varnish the teak, clean the bilge, and light a candle in the galley for good measure. And when the right buyer comes along, hand over the keys with a smile, a handshake and maybe a little tear.
After all, it’s not just a boat—it’s a piece of your life, setting sail for a new horizon.
