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The Day You Sell Your Boat

How does the saying go? “The best days of a boatowner’s life are the day you buy the boat, and the day you sell it.”

But how do you know when it’s time to sell the boat? When does the fun-and-freedom-to-dollar ratio become unacceptably skewed and dig too deeply into your wallet? How hard — or easy — was it for you to cut ties and put your boat in the Classifieds?

We’re really asking, Latitude Nation. Please comment below, or email us here, about the agony — or ecstasy — of selling your boat.

Singlehanding my Columbia Challenger — as I was here in late summer 2018 — has been a surprisingly rewarding experience.
© 2019 Latitude 38 Media LLC / Tim

I find the ‘day you sell your boat’ aphorism to be ridiculous. I have had several life-changing days on my Columbia Challenger Esprit to which I could ascribe no price.  Any sail, simply any sail, wind or no, crew or no, has been worth every penny in slip fees. But still, the time has come to make some tough choices.

Well, maybe.

To be fair, I put Esprit up for sale once back in 2017, but then started sailing and falling in love with the boat, and with San Rafael Canal and Bay, and China Camp. Being the first boat that I owned, the little 24-footer has been a learning experience in singlehanding, anchoring, basic maintenance, teaching friends how to sail, and generally getting comfortable on San Francisco Bay.

Why sell it?

I simply cannot justify that fun- and freedom-to-dollar ratio anymore. To be fair, my slip fees are incredibly reasonable in my part of the San Rafael Canal. Still, if I sail Esprit three times a month — which would be a lot, for me — that still comes out to a hefty per-sail monthly total. As it is, I sail roughly once a month at the most.

The totally decent Esprit.
© 2019 Latitude 38 Media LLC / Tim

Here’s what I would prefer:

Is there anyone who might be interested in a partnership? I would love to stay involved with the boat, and find a few people that love her as much as I do.

I’m not going to lie — she needs work; she needs to come out of the water and get a fresh coat of paint from top to bottom. And then the ‘might-as-well’ jobs begin: Might as well drop the mast, inspect the rigging and replace a few old blocks. Might as well run a new main halyard, as the wire section of the current one has a few meat hooks. Might as well throw a coat of paint on the interior. Might as well, might as well.

And so it may go.

San Rafael Bay has been a gift that has kept giving.
© 2019 Latitude 38 Media LLC /

It is this regular but necessary maintenance that has proven a last straw of sorts — justifying slip fees for minimal use was one thing; justifying a trip to the yard for 10 to 12 sails a year is another.

The boat has many pluses — Esprit is a solid vessel that’s bone dry in the bilge; I’ve had her out in 30-plus knots bashing into the ebb without a second thought. She has an outstanding Honda eight-horse motor. If money were not a factor, I would restore her to like-new condition. In Webb Chiles’ spirit, I would (seriously) make her bluewater ready and sail her to Hawaii.

So, if you’re interested in ‘coming aboard’, please let me know at [email protected]. Otherwise, look for Esprit in the Classy Classifieds in the coming months.

7 Comments

  1. Malcolm Milliron 4 years ago

    A very nice piece. Well written and points out almost all the pros / cons of keeping or selling.

    We keep our MacGregor 26-X right outside our living quarters and several times a week we go sit in the cabin
    and relax, read, watch TV, sometimes cook and stay aboard overnight. That way we can enjoy it all year long.

    I do hope that someone comes forward and says ” I want to be a part of this boat, and enjoy it”.

    MM

  2. Jim Gossman 4 years ago

    Tim, I totally get the whole “happiest days thing” in spades…since our previous boat took almost three years to sell (with never ending ads in your cc’s (and other mags). It was a fine Fisher 30 which I’d spent six years putting my heart and $$$ restoring/repowering, but seemed to attract only dreamers. We still used her far more than average, but once we decided to sell, the mixed emotions were painful. We’ve since found our forever boat, which I’ve told you about before, and her
    trailerabilty has already lessened the sting of expenses and worries in the off-season. I just singlehanded her home to the Benicia launch ramp, and it was a fabulous finale to a great season. I appreciate your printing several of my previous comments, and hope your boat finds a new caretaker. Beware, another vessel will seek you out!! Happy holidays.Regards, Goose

  3. John and Debby Dye 4 years ago

    The day of reality came to sell Lovely Reta during this past summer. After Debby’s 2 back surgeries resulting from putting Lovely Reta away for Hurricane season we realized after 40+ years of cruising it was time to find another way to spend time on the water. She is currently for sale and advertised in Latitude 38.

  4. Sam 4 years ago

    What a familiar dilemma. I have mulled over two ways of quantifying the costs and benefits myself:
    1. The “price per sail” measure: Annual cost of ownership / sails per year. This one never makes me feel good, no matter how often I get out on the water. I don’t recommend this metric, because I don’t think anyone would ever see the numbers come out in their favor.
    2. The “how long does this delay retirement” measure: considering if I saved what I spend on the boat over the next 20 years or so, how far out would this push my retirement? Based on my estimates, this comes out to something like 2-3 years. Can I work 2-3 more years in exchange for the joys and satisfaction of boat ownership for the rest of my life? In my case, the answer is yes, so I happily keep the boat, even when it doesn’t feel like I use it enough. How many more life changing trips in and out of the Bay will I have because the boat is mine, free and clear to use whenever I want? And if I don’t have a boat, how the heck am I gonna fill my time otherwise?

    In the end, owning a boat is pure privilege and luxury; the costs only make sense if you can afford everything else you need in life. And then the only question that matters is: is this how you want to get your thrills?

  5. larry long 4 years ago

    With your connections, you might consider joining a club and sailing a variety of boats when you have the time. Then when the time comes again for ownership, you will have had allot of different experiences with different boats, and can report those to us here reading the “Great Latitude 38”.

  6. Steve Zevanove 4 years ago

    Good article. The decision to sell is always a tough one. The truth is owning a keel boat is expensive. Generally, you can buy a nice boat for the price of a Honda Civic, but the maintenance and other reoccurring costs can be substantial. It depends on how you use the boat, but even for folks that aren’t serious racers, you can generally figure on spending 2 times berthing as your annual expense. My Islander 36 berthing is ~$425 per month in Alameda, so I figure the total cost of ownership (berthing, insurance, Maintance, etc..) is about $850/month or $10,000 per year. Even if I owned a smaller boat (I used to have a Merit 25), it is difficult to berth and maintain a vessel for less than $500 per month or $6,000 per year. Bottom-line: not a cheap recreational activity.

    On the other hand, we have had experiences on the boat that will be with us for the rest of our lives. These are precious memories like: weekends buddy boating with friends and our kids, racing in our local club series, making friends in our active association, taking my son’s college friends sailing under the GG Bridge, watching the Blue Angles fly,…the list goes on and on. There is really nothing so special as taking people new to sailing on their first outing on SF Bay. You really get in touch with how special the experience is when you see it through others.

    One last point. While owning a sailboat is expensive, almost all special experiences are going to be costly. Take a family of four to a Pro football game, and you will easily drop a grand for one game. Take a family of four skiing for the weekend and you will easily drop two grand. When my son was traveling for college baseball recruiting tournaments, we would spend a few grand on fees, lodging, food, and transportation for a week long tournament. Do an overseas Backroads Bike Tour and you will spend five grand per person double occupancy, without airfare. Considering all of this, our boat feels like a pretty good value to me.

  7. Jerry Shell 4 years ago

    Tim my vessel owned me over 30 years. I’m a musician, and for 13 of those years, almost every weekend I sailed 13 miles from my marina on the east side of Charlotte Harbor to an inn and restaurant on an island in Pine Island Sound, FL 1984-1997. I was “required” (I loved it!) to live aboard as a condition of my employment. No road there. So I was able to deduct all of my expenses-slip fee, gas for the outboard, supplies, hauling and maintenance-everything. Sailing and being around my vessel, living aboard her when I was there-was my life-my soul. Extremely grateful for those years. As editor of an excellent major sailing magazine, you could find a way-you already use her in your business-maybe transfer title to the business. Check with your accountant. Fair winds and following seas. Jerry Shell

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