How we got into sailing

What started as one wind powered hobby of flying planes in 2015 evolved into numerous boats and now, 10 years later, into living aboard our 4th boat, SIRI.

Ever wonder how the heck we, two people who were most recently living in South Dakota and working in agriculture, got into sailing and are now living on a boat full-time in Canada preparing to head offshore in 2026? Here's the full story...

The beginning of wind-powered hobbies

I primarily flew this Cessna 172 and another very similar to it, while getting my license .

I moved to South Dakota in April of 2015 to begin working for a livestock supplements manufacturer handling technical support services while Danielle wrapped up the last year of her graduate studies in ag marketing & comms in Kansas. As is apt to happen when left unsupervised (and now armed with an income), I decided it was a great time to take up flying small planes and to get a pilot license.

While working to get my license, I got to the step where I could fly without an instructor (solo) but still with limitations, one of which being wind speed/angle to the runway. Now needing something to do with my spare time on days it was too windy to fly, and armed with a high-speed internet connection, I knew that sailboats take wind; the only logical thing to do was to visit Craigslist, at which point a search for "sailboat" turned up a reasonably priced Hobie 16.

Hobie 16

Pointy end up and above the water.

Now the proud owner of a 1970's era catamaran, and no earthly idea how any of it worked, another internet visit was in order. This time it was a foray down a YouTube rabbit hole where you can find a video on how to set up (rig) a Hobie 16 and what parts do what. Logically, you do this in your driveway so that nobody can laugh at you as you inevitably take three times longer than you should and must do each part twice (incorrectly first, of course). Having successfully got the pointy end up and the sails on, a maiden voyage was in order. Following a quick safety stop to pick up a life jacket (you're welcome, Mom) the drive to Bear Butte Lake commenced.

Bear Butte was strategically selected for numerous reasons; firstly, it is small enough that there wouldn't be too many people at the boat ramp to get a free comedy show while setting up the (hopefully) floating bananas, and secondly there was a reasonably high probability that when the boat inevitably capsized in the middle of the lake, a swim to shore was very achievable. At this point, Danielle was now living in South Dakota. However, instead of joining the maiden voyage, she made the logical (and boring) choice to stay ashore and photograph (for life insurance purposes, probably).

Catalina 22

Boat #2 moved into what was boat #1's parking space.

Having successfully not sunk the Hobie after a couple of outings, and realizing it was a bit too small (and fast) for our likings, an upgrade was in order. Enter Facebook Marketplace (circa 2017) and a slightly newer 1970's Catalina 22. Once again, hello YouTube for a search: "How to setup a Catalina 22".

Now being experienced sailors (at least twice), it was time to broaden our horizons and explore Pactola Reservoir. An admittedly far more scenic location than our previous sailing forays on Bear Butte Lake, and caught in a moment of weakness, Danielle agreed to be aboard the boat's maiden voyage to better see the views.

Taking in the sights at Pactola Reservoir (shortly before the gooseneck broke off the boom).

Boat successfully off the trailer, into the water, and a mostly operational outboard (again, 1970's vintage) propelled us away from the docks and into the deep blue. After getting up both sails, and while lackadaisically meandering around the lake going generally in the direction we wanted to, we gybed to return to the docks, at which point our gooseneck decided to give up the ghost and come apart. The gooseneck is what holds the boom (horizontal stick) to the mast (vertical stick) and keeps the main sail doing what it's supposed to.

Fortunately, the winds were light and we managed to drop the whole lot onto the deck before having a long conversation with the outboard motor on why now would be a particularly good time to run.

Lots of South Dakota sunsets from the cockpit of that Catalina. Even the dogs joined in on the sailing fun a few times.

It was also around this time that we discovered there is a sailing club in western South Dakota (who knew), and, even better they do a sailing course as part of the community education programs.We quickly enrolled.

After attending the Black Hills Community Ed sailing course, and joining our first yacht club (Angostura Yacht Club), we sailed the Catalina at different lakes in the area (Pactola Reservoir, Angostura Reservoir, and Orman Dam) a number of times.

Seaward 25

Feeling more confident in our sailing abilities, we decided that an upgrade was (again) in order. This began the side passion of every sailor and armchair sailor around: an infatuation with YachtWorld. YachtWorld, for those non-addicts who didn't immediately begin salivating at the word like a fat-kid does for chocolate cake, is an online brokerage of all manner of floating craft around the world. Like all good drug dealers, it has something for everyone's tastes from mild to wild.

The listing photo of the Seaward 25.

Our trailer-based limitation helped to keep the price tags in the low 5-digit range although you can find trailer-able sailboats in the low to mid 6-digit range without a challenge. Through numerous online forays, we decided that a Seaward 25 would be the ideal new boat for us. It is a trailer able, shallow-draft vessel made in Florida with a very high-quality reputation, and most importantly if we looked at vessels in the 15–25-year-old category was within the budget. We soon found the ideal boat, although, naturally, it was across the country in Anacortes, Washington.

Enter a quick flight deviation from a work trip to do an initial inspection, followed by a road trip a month later to collect and bring back to South Dakota which began one of the more comical (in hindsight) cross-country trips we've ever taken.

Initial inspection and sea trials completed to satisfaction, we arranged a four-day weekend over Easter to drive from South Dakota to the U.S.-Canada border in North Washington, a mere 2,400 miles round trip across seven mountain passes each direction…shouldn’t be an issue.

First time seeing the Seaward when I made a trip up to check her out and see how she sails.

The boat was resting in Anacortes, Washington, (about halfway between Seattle and the Canadian border) but was owned and registered in Canada so collection involved having to cross the border to complete the sale and then import the boat into the U.S.

The then current owner kindly arranged for the trailer to be fully serviced before our arrival with new wiring, lights, and brake and bearings so that we would have peace of mind towing a fairly large trailer halfway across the country. However, the yard manager where the boat was parked on its trailer was kind enough to undo much of this work by picking up the tongue of the trailer on a forklift and dragging it perpendicular, completely separating the bearings in the axle, which we discovered approximately 10 miles south of the Canada border as we were following the boat up the interstate (towed by the current owner) while watching a large volume of smoke and bright colors precariously coming from one of the wheels on the trailer.

We were able to pull off in Blaine at the last U.S. exit northbound where we discovered that, with very little effort, we could take the wheel (including the hub) off the axle spindle utilizing no tools. Fortunately, our exit also happened to be a marina with a small boat ramp so removing the boat from the trailer made it significantly easier to repair the trailer… which would have to wait a few days until the coming Monday when stores reopened from the holiday. On a plus side, we got to spend a couple nights on our new boat in the Blaine Harbor Marina while we waited.

Monday afternoon and trailer bearings replaced (again), we were back on track to do an out and back across the border to complete the sale only two days behind schedule. With the Seaward firmly attached to the back of our own vehicle, I made the U-turn headed back to the U.S. to complete the import papers and collect Danielle and the two dogs who had stayed behind at the boat ramp from lack of vet paperwork. It turns out, self-importing a sailboat from Canada to the U.S. is not standard practice at the land border crossing, but fortunately a kind customs agent took pity on this nimwit and helped expedite the wheels of bureaucracy to move at the accelerated pace of only four hours.

Bearings fixed, border crossed, boat officially in our ownership, and ready to get back to South Dakota. What else could go wrong?

Back into the states, I made a quick pitstop to load the remaining passengers, and then we were off down I-5 like a herd of turtles headed for rush hour traffic in Seattle. Somewhere between Everrett and Seattle there was an odd wobble coming from the trailer that wouldn’t go away, so we made a quick stop into the nearest interstate rest stop to inspect. It turned out that since the wheels were still attached to the hubs at the mechanic shop in Blaine, and perhaps in haste of trying to get us on our way as quick as possible, they neglected to tighten the lug nuts after installing the new bearings, which ended up removing all the wheel studs, which allowed us to, once again, remove a wheel from the trailer without the use of tools. Thankfully, we were parked when the wheel separated from the trailer.

Wait... where are the bolts?

Realizing we were in a sub-optimal location, we Googled the nearest service station that was still open and loaded Danielle into an Uber along with the hub to head to Les Schwab for a new hub, wheel, and tire while Ethan stayed with the pickup, boat, and dogs. After arriving at Les Schwab Danielle explained to the owner “I need another one of these, but with all the pieces not broken” (or something like that) and told the story of where we were and what had happened. Upon realizing where we were broken down at, the kind owner launched into a fit of helpfulness pronouncing not only that we were in a terrible location and that there is no way he is letting us do the work there, but that he would drive Danielle back himself and get us jury rigged to make it to back to his shop to repair everything correctly the next day.

Meanwhile, I was learning why the owner of Les Schwab was reacting how he did when told where we were parked. The first telling incident was a middle-aged man in a yellow rain slicker who came up to my window to ask for a ride (I’m not sure how the jack holding up the trailer that he walked by didn’t give him the hint I wasn’t moving far). With nothing on but a rain slicker, and offering me an uncomfortable wink, I kindly passed on his company, and he prowled onward to check with other motorists for who could give him a “ride”. Next up arrived the Breaking Bad-style motorhome complete with tinfoil over the windows. Out pops the stereotypical pot-bellied, shirtless, neck-tattoo guy walking an overweight pitbull complete with his lady friend in lockstep who also fit the stereotype. A quick walk about, then back into the motorhome, up pops the roof fans and out rolls smoke (smelling more of chemical than skunk). Moments later, a car pulls up. The driver gets out, looks around, and proceeds to nervously knock on the door of the motorhome. Mr. Neck Tattoo sticks his head out and does the same nervous look before they both retreat inside. Couple minutes later, while the ensuing smoke continues to roll out the vent fan, the car driver saunters out of the RV and goes back to his car. The cycle continued.

Note the detached wheel behind us next to a school bus and the nose of an older RV, aka the rolling meth lab of interest to numerous visitors of this particular rest stop.

Not wanting to get shot, shanked, or robbed, I opted to mind my own business, but made sure that there was a large crescent wrench in my door pocket and a very loud Malinois in the back seat ready to go if needed. Meanwhile, rain slicker man found himself a ride in a vehicle parked in front of the men’s room…curiously, they never left the parking lot before he got out of the car. After about 30 minutes, a school bus pulls in. The driver gets out and heads to the restrooms. On his return, he doesn’t go back to the bus but instead heads to the motorhome. This reached my limit of “to each their own” as I’m fairly certain that combination doesn’t bode well while driving busloads of children. I call into the local non-emergency number and explain where I was currently parked and that there is a rolling meth lab straight out of Breaking Bad next to me where a school bus driver had just entered, and by all appearances, partook, and that the bus number and license plate is yada-yada. The dispatcher informs be that they’d send someone out soon to check on it.

Another half-hour goes by, and I called my friendly dispatcher back to ask if they were sending anyone, to which I learned there was a “minor” shooting and homicide just down the street so they were a little tied-up, but somebody would be by when they were available. Soon thereafter, highway patrol shows up and our neighbors end in the back of the car (shocking, I know). At the same time, Danielle and the Les Schwab owner arrived (he may have been wearing a cape complete with a red S) where he quickly fit a new spindle, hub, and wheel, and led us back to his garage. After dropping the boat and trailer at the shop, and locking it in their storage yard, he told us he’d change his schedule first thing in the morning, and that they would have the trailer axles rebuilt (again) and new wheels and tires as soon as possible the next day. At the recommendation of the Les Schwab owner, we were off to a hotel some distance down the road for the night (a new methadone clinic had opened across the street and apparently the clientele was not always friendly).

The next morning, we arrived early to collect the boat and trailer that had been repaired as quickly as promised to impeccable standards (at this point, impeccable standards equaled wheels staying on without blowing up bearings) and thus begin day six of a four-day trip with only a mere 1,000 some miles to go back to South Dakota. Fortunately, that leg was as boring as we could have hoped for.

Safely back in South Dakota as the proud new owners of a Seaward 25, we immediately started planning for the upcoming 2019 sailing season. We were lucky to land a slip at the Angostura Reservoir Marina, which saves nearly 3-4 hours of setup time and each time we wanted to use the boat. Most weekends were spent at the lake during the summer given that the boat was more or less a small floating RV, complete with bed, kitchenette, sink, stove, and bathroom. The previous owner had also spent a considerable sum on a full cockpit enclosure (essentially a tent that fit over the outside seating/steering area) that allowed us more covered space even during the infrequent rains.

During this time, we also became more engaged with the local sailing club (Angostura Yacht Club) and accidentally became contributing members. What I can only assume was a total lapse in judgement by the adults in the room (not us), we somehow came to assist with the sailing ed classes and were responsible for helping teach the newbies (which we still were, and are). Having not heard of any major travesties from the fresh South Dakota sailors, I can only assume they completely ignored every word that come from my mouth.

A key selling point of the Seaward was the fact that it was trailerable. This may have been somewhat exaggerated in order to sway the decision of one person…who is to say. But, in only a few short hours (3-4) you could go from the boat being on the trailer to in the water and moving, and at the end of the day it took only 2-3 more hours to get it tucked back onto the same trailer to mosey down the highway. The idea being that we could load up the boat, head to a different body of water for a few days to go sailing/camping and then load back up and head home. The only caveat to this was, with the boat already being in a slip at Angostura we needed to double our time: One weekend would be spent collecting it from its home slip, with the next weekend hauling it somewhere to use, and then reverse the process. Being an inherently lazy person, why go to the effort of taking down, hauling, setting up, taking down, hauling, and re-setting up when instead you could just load the cooler and stay in one spot? Or better yet, what if the boat was already somewhere new and we just travelled there…

Thus began the discussion of, “Should we moor (park) the boat somewhere new? And if so, where?” One area of interest was actually where we bought the Seaward from: the Pacific Northwest. It fit well in our life in that the season to be there is summer (which was typically slower work wise), has lots to see within a short sailing distance, good services, safe and easy sailing in protected waters, and “reasonably” accessible flight from South Dakota. The next, and really only, logical progression of thought soon evolved… “What if the boat moored there was maybe slightly bigger…like with standing headroom…  And if it’s already in the area, there is no need to be trailerable…”

Enter the relapse of the addiction that is YachtWorld.

Waterline 47 (SIRI)

Ethan's first time seeing SIRI, escorted by our buyers broker, Max Shaw.

By fall 2021, the “big” boat shopping endeavors (read: addictive YachtWorld scrolling) was in full swing.

The search criteria progressed what is normal: start by looking for things way outside the budget and then wrangle down the compromises. In the yachting world, on the spectrum of champagne to beer budget, we fall fairly close to the “fighting a raccoon for a half empty dumpster beer” end of the spectrum. Since we did not in fact win the lottery (I hear that buying a ticket would have helped the odds, although only marginally) and that we were fairly certain in the general location we wanted to be, we enlisted professional help in the form of an experienced sailor/teacher, John Neal (Mahina Offshore Services), who had a boat purchase consultation service and helped to direct us to a few boats we hadn’t considered along with recommending a buyers broker in the area with real world sailing experience (special thanks to Max Shaw and Yacht Sales West).

Through this process I ended up rerouting a work flight home in February 2022 to go through Vancouver Island, B.C., Canada, to look at 2 of the boats John recommended, one being a total bust (way more project than we wanted) and one being SIRI. We eventually put in an offer and, in April, went back with Danielle in tow to do sea trials, pre-purchase survey, mechanical inspection, haul out, and ultrasounding (common for metal hulled boats). After a bit more back-and-forth, we signed on the dotted line and began to throw burning money into our own little hole in the ocean (this is what a boat is). Thankfully, this Canadian boat purchase went far smoother than the previous one.

One of our first outings on SIRI as her new owners in 2022 was a trip to her former owner's dock and boat house in Montague Harbor to collect additional items they had stored and thought we might find of use. We had a nice time getting to know the former owners, and have stayed in touch ever since.

Moored in front of the iconic Empress Hotel in downtown Victoria, B.C. on Dec. 3, 2025.

The boat search started as, “a slightly bigger boat that we could go vacation on to get away from work”. As anyone who has owned a boat knows, if you rearrange the letters in boat it spells "work". The more time we spent working on the boat, and sporadically enjoying it in the PNW, the more we thought about the “someday” where we could retire and sail to other places (to work on the boat).

Over the span of an undisclosed amount of time, one unnamed spouse cajoled the other into considering that “someday retirement” could be a mid-life pre-tirement…And this is how we find ourselves today, living aboard full-time, moored in Victoria, B.C.’s, inner harbor to watch the harbor Christmas lights event as a few day respite from a winter of boat projects before a spring departure for an indeterminate length cruise to places less seen.

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