I Purchased a Wind and Human Powered Sailboat for $450

Ever since my first bicycle expedition across Latin America, back in 2001-2002, I’d been dreaming about building or acquiring a wind and human powered sailboat for my next great adventure. Initially, I’d thought about building a multi-hull vessel that incorporated bicycling mechanics for human power to sail from the Chesapeake Bay to the Amazon Rainforest. This is a sailing goal that very very few people have attempted, as documented by a modern day sailor who accomplished the feat himself, Stephen Ladd. In fact, Mr. Ladd and his wife voyaged to a very unusual and remote section of the Amazon that in recorded history, more people have walked on the moon, than have sailed in this particular area.

I let the idea stew for almost two decades, and for the longest time it was just an abstract fantasy, that I would occasionally nurture each year with some reading or research into either canoe trips in exotic places, sailing canoe and sailboat books which I collected, travelogues of people who canoed that kind of distance, etc. I also indulged in pirate literature and research, the Black Sails series, freediving, and in particular, research and writing into Polynesian nautical architecture, lore, and navigation.

Around 2015, a close friend of mine, Dean, invited me to help him refit his 40 foot, Atkins designed, ketch rigged sailboat in Bermuda. I was more than happy to come along and help out. For the next five years, I helped him refit his sailboats, as well as other friend’s sailboats in places like Florida, and I learned a lot about maintaining large boats in the process. I learned how to do bottom paint, repair fiberglass hulls, waterproof fittings, diagnose and repair gas engines, work on diesel engines, and install boat electronics. Along the way, I learned quite a bit about sailboat architecture and Western sailing maritime culture.

But I never learned to sail. All during this time I stewed on my sailing idea, waffling between multi-hulls like Wharram Catamarans and CLC Boats Madness Proa’s, to Michael Storer’s Goat Island Skiff, Kombi Sailing Canoe, and Bedard Designs River of Grass Micro-Expedition Cruiser. I fantasized about competing in the Everglades Challenge, or the Texas 200. In my entire life, I’ve gone sailing maybe five times, twice at Boy Scout Summer Camp where I failed my sailing merit badge sailing a Sunfish, once with a friend at the MIT sailboat club, and twice in Bermuda on a ten foot Trinka sailing dinghy.

For a while, I became enamored with Polynesian Proa’s till I realized that payload capacity is a major factor for expeditions, then I explored largish monohulls, if it weren’t for the fact that most were too large, with too deep a draft to take on the shallow, gunkholes that one would encounter on an expedition of the type that I wanted to embark on. Over the years, I came down something larger than a dinghy, yet not as bloated as a cruiser, with the ability to be human powered like a proa, yet with a large payload than a multihull.

I told my friends over the years about my idea, but it wasn’t until an acquaintance of mine convinced me not to build a boat, but to consider buying one at a charity auction held by a local maritime museum on the Chesapeake Bay. I thought about the idea, and decided to give it a go. I wasn’t convinced that I would find the sailboat that would fit my needs there, but then again, I had no idea what would be at that auction.

My needs regarding a sailboat are based on my personal philosophy that I developed over two epic bicycle expeditions across Latin America about how to execute an adventure. The ethos is keep it simple, keep it light, keep it effective. For a sailboat, that meant it had to be under 20 feet long, trailer-able or car top-able, and it had to have a shallow draft adjustable keel. The amount of work I saw and put in with my friends boats, which were all in excess of 35 feet, was enormous, and I never saw any time sailing them. However, I did want some amenities for the boat. I wanted a cabin to sleep in, a compact galley, and some storage space.

More importantly, besides wind and some motor power, I needed an element of human propulsion. That last requirement is why I kept considering custom made, DIY one off designs.

With that in mind, I went to the charity auction at a local maritime museum with Dean and friends, and I was actually amazed at the sheer variety and selection of boats that were on display.

The first boat I looked at was a Nimble 20. I’m familiar with Nimble’s, since a Nimble Wanderer is one of the boats in Dean’s flotilla that I worked on. This Nimble 20 had a lot of amenities for such a compact cruiser. It was also trailer-able.

Dean tried hard to convince me to put a bid in for that boat. And to be fair, I did lay in one of the bunks with the sounds of Central American jungle birds in my ear, imagining myself waking up in some tropical river, sailing up it from the Gulf of Mexico. I got back out into the cockpit, and sat down, admiring the boat and thinking about it. Dean walked up to the side, looked at the boat, then me.

“Come on Dave, live a little.” Dean said.

He had a point. When I first moved to the D.C. area in 2014, I came with a dream to create a high tech company start up with some technology that I developed as my thesis back in my engineering days. I suffered financially and professionally from 2014 to 2020, often living below the poverty line. Then 2020 happened, the lockdowns happened, and a side job I took at a bike shop suddenly took off because people lost their minds, and bought outdoors equipment like bicycles like crazy.

Now it was September 2022, and my financial and business fortunes had done a complete 180, and here I was, at a boat auction, shopping for a sailboat. The realization of where I was versus where I was in 2019 was stark and surreal. All those years of struggle to survive while trying to get a dream working didn’t feel that distant. Yet here I was, with a budget, and an adventure goal of attaining a sailboat to accomplish some long dormant adventure goals.

“I do need to live a little,” I told myself as I stared at the Nimble 20.

But something about the boat turned me off. She had a big ass, which is to say she was a chunky, squat boat, and looking at her and getting into her made me think that I couldn’t get her down my driveway. And I didn’t see any way to add a human power element to her.

As the auctioneer got near the Nimble 20, Dean realized he wasn’t going to succeed in getting me to consider bidding on it, so about 15 minutes before the auctioneer got to the Nimble, he pointed me to a boat just before it, and suggested I take a look at that one.

We walked to the boat, and at first, I wasn’t impressed. She was about the same length as the Nimble, definitely slimmer, and she sat low on the trailer. Then I saw she had a bowsprit. What was a boat this size doing with a bowsprit? That caught my attention. All of her parts were piled up on top. So I climbed aboard, looked down, and got in the cockpit. I looked inside, and saw a pair of oars.

That was it. This was the boat for me.

I got out, grabbed my pamphlet guide, and looked her up. She was a Blockley Privateer 20, made in the UK, and apparently stored in a garage since 1994. There wasn’t much else in terms of information about her. And like many of the other boats at the auction, the trailer was included.

The auctioneer got to her, and I walked over to the gathering to start the bidding process. The bid price started at $75. I raised my hand. $80. Another guy raised his hand. $95, I raised my hand again. $100, the same guy raised his hand. It went on like this as a bidding war between me and this other guy until the price hit $450. No one else was bidding on her. Strange. I raised my hand, and I had a sinking feeling that I wouldn’t win the boat, since I figured I was going to be outbid. I wasn’t willing to go past $500. The auctioneer raised the price to $475, and the other guy didn’t raise his hand. Suddenly, I heard the auctioneer say, “$475? Anyone? This boat for $450! Anybody? SOLD to the man in the cool hat!” He pointed at me, declared me the winner of the boat, and at that moment, a state of shock set in.

Did this just happen?! Did I just win this boat, trailer, with everything in it for $450?! I was in shock. I was also a little scared. How was I going to get this thing home? I didn’t have a car. Where was I going to put this? I wasn’t concerned about money, as I budgeted about $5K to build and outfit a boat for myself, but I was concerned about the logistics.

As for the Nimble 20, it sold for about $2100. Which is still an incredible price for that boat.

After the auction, everyone congratulated me, and I went to pay for it. I also had to get the title and the registration. I had a million questions in my head, that could be summarized as, “What did I just get myself into?”

After we left the auction grounds, we went out for pizza in Saint Michael’s, where I sat silent, still in shock, munching on my pizza.

But I didn’t have to be concerned. My friend who suggested I go to the auction let me park the boat in her yard at her cottage, and it was a simple matter to hire a local truck run by some Hispanics of a landscaping company across the street from us to tow it for us to her place where Dean and I could inspect her.

The next day, while we arranged for tow, I went through my new boat to get an idea of what was on it.

I was amazed. The gear on the boat was in immaculate shape. It turns out the previous boat owner kept the boat in a garage since about 1994-1995. The entire sail kit was there, all the rigging, the spars, battens was there. She came with a main sail three jibs – a storm jib, yankee jib, and regular jib – and a topsail. She was a gaff rigged boat. Talk about old school, but that also meant I had a literal Pirate Ship! There was emergency gear, modified hardware, anchors and chains, lots and lots of ropes and lines, and everything was in great shape. There was no outboard motor and no electronics, which was great because I wanted to create a mostly analog system on her. The question I had though was the most important one.

Does she float?

We towed her back to my friend’s place, and two weeks later came back. I purchased a towing hitch for Dean’s SUV, and that weekend, we took the boat into a nearby launch to see if she floated. Which she did. And the oars worked, though rowing her was like rowing a truck. But I managed to get her out of the dock and to one of the pilings!

I literally bought a unique sailboat, with sails and rigging in great condition, emergency gear, charts, most of the accessories, a trailer with replacement bearings, for about a year’s worth of cheap beer.

I bought a freaking sailboat with beer money.

Over the next few weeks, we made multiple trips to the boat to repair the trailer and set it up with turn and stop signals, repaint it to protect against corrosion, setup and test out the sails, test out how she sailed, see if the systems were working, and to see if there were any extensive issues like longer term leaks, hull and deck issues, etc. She sailed through, no pun intended, with no real problems whatsoever, other than sitting in storage for a very very long time and seriously needing a very deep cleaning and re-organization.

I also did a lot of research on the sailboat, and there wasn’t a lot of information about the Blockley Privateer 20 that’s open and in the public, other than some basic sailboat data. I had to find and join a special interest group around the boat which is the Special Interest Group on groups.io. The Privateer 20 is definitely a unique sailboat, and considered a “character boat. For starters, she’s a production gaff rigged sailboat, and ever since the 1940’s, there haven’t been a lot of gaff rigged production sailboats out there.

The other thing is her unusually designed swing keel which is further forward than most sailboats designed with a swing keel. Apparently, this creates some unique sailing characteristics that only a Blockley Privateer can have. It’s still Greek to me at this point in time, but this year in 2023, I will be taking her out a lot more often after some refit work during the summer.

This all happened in 2022. Once we got to take her out a few times to test her sail rigging, to see if a motor worked, and to inventory the items she had on board, it was time to pack her away for the winter and to start planning for 2023.

And boy, have I got plans.

To Be Continued…