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Enabling a Low-budget Boat Flipper

The author’s happy client makes a phone call from aboard her new purchase

The author’s happy client makes a phone call from aboard her new purchase

It was a simple craigslist ad that started all the rumpus. A guy named Milo in Belfast, Maine listed a well-worn 1969 Tripp 29 sloop for sale for $6,000. A young acquaintance of mine, Emily Greenberg, who maintains an intriguing sailing blog at and sometimes writes for SAIL, was on it like a dog on a squirrel. Grabbing it by the neck and shaking for all she was worth.

First, she sent Milo several e-mails, to which he didn’t respond. Then she called me up and ordered me to send Milo an e-mail saying I wanted to buy the boat. Her thinking was that maybe he’d respond to me since I’m a rich-and-famous whatever it is I am.

Sure enough, he did. He explained he was overwhelmed with responses to his ad and hadn’t had time to separate “the wheat from the chaff,” but since he’d recently read my book (The Sea Is Not Full, Seapoint Books, 2017) I automatically rated as wheat.

When I told Emily this, she said that meant Milo must be an old guy like me, since obviously, no young people would ever read my book. The following day I drove up to Belfast with a checkbook in my pocket and was pleased to find Milo was, in fact, still pretty young. Ka-ching! Score one for the geezers.

Emily, who was on a boat she already owned in Florida at the time, insisted she wanted to buy this one sight-unseen and urged me to hand Milo a check ASAP before some other opportunist swooped in and tried to grab it (as, indeed, another aspirant already had, preemptively offering $7,000 and making this the new asking price). Being the traditionalist that I am, though, I insisted on inspecting the boat and asking Milo some questions about it first.

It was actually a pretty cool boat, with a solid, hand-laid glass deck and hull, so no soggy-core worries anywhere. The standing rigging and chainplates had recently been replaced, and there was a fresh roller-furling unit on the headstay, a fully functional windvane on the transom and bronze hardware everywhere. Most intriguingly, a custom 48-volt electric motor had taken the place of the old Atomic 4. The only downside was the boat was downright filthy. Having already received over two-dozen answers to his ad in less than 48 hours, I assumed Milo had decided he needn’t clean the boat up to show it.

After answering my questions, Milo had a question of his own: why the heck was I interested in his boat? Busted! I came clean and admitted I was, in fact, acting as an agent for a friend, who Milo immediately guessed must be Emily. He still took a check from me, though, and handed back a handwritten receipt. That same night Emily reimbursed me via Paypal. The deal was done.

The thing is, this is the fourth cruising sailboat Emily has purchased in five years. Her previous yachts were a Bristol 24, a Pearson Ariel 26 and a Great Dane 28, all of which she has lived and cruised on full-time. It may seem crazy, but this latest transaction, exchanging the Great Dane for the Tripp 29, actually made good sense economically. Emily had purchased the Great Dane for $4,000, sold off its engine and wanted to upgrade it with a windvane and roller-furling. It was much cheaper, though, to buy the Tripp, which already had those things, than it was to install them in her existing boat.

I have to say, the volatility of the super-low-budget cruising boat market has surprised me. I noted with interest, for example, when finalizing our paperwork, that Milo had made a tidy profit of $2,000, even though he’d owned the boat for only a year. Emily also had no trouble getting what she paid for her Great Dane, plus $200, even though it now has no engine. In part, I am sure this has something to do with the Covid-19 pandemic, which has sent people everywhere searching for escape vehicles. I also think, though, there is a growing market of young folk looking to go cruising in ultra-affordable boats, an encouraging trend. As for Emily, I reckon she’ll eventually flip her way up to a superyacht. If she wants me to represent her in that sort of a deal, though, I’m asking for a commission. 

July 221



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