Aaron here. I trace my interest in sailing to almost 3 years ago when I found the SV Seeker YouTube channel. This is a guy named Doug that is building a 74-foot steel sailboat in his front yard in Tulsa, OK. I think at the time I was more interested in the spirit and scale of what he was doing than the fact that it was a sailboat. He lets people come help him and teaches them any skills they may need for the work--often welding and grinding.
I mentioned this to my dad that summer (2016) and in October we went down there on our motorcycles to help him for a weekend. When we arrived Friday night we spent a couple hours grinding the edges of the portholes. On Saturday we started manufacturing the floorplates that do double duty as the tops of the diesel tanks in the bottom of the boat. I ran a CNC machine with a plasma cutter to cut out the shapes of the floorplates and hatch covers, and my dad drilled and tapped hundreds of bolt holes for joining the two together. On Sunday we worked on welding a cast iron threaded fitting into each hatch cover. The SV Seeker video that includes our time in Tulsa can be found here (https://www.youtube.com/watch?v=Td707cC8UW8); my dad and I are introduced at the 5-minute mark.
Then other sailing videos kept being suggested to me on YouTube. I watched a few and soon those were all I was watching, trying to learn as much as possible. Sailing books started arriving in the mail. Probably during the spring of 2017 I began to think that going cruising was something I was actually interested in doing (Anna wasn't opposed, but maybe didn't think it would actually progress this far!). I figured that I should probably get some sailing experience so drove to Bismarck to buy an 18' 1976 Chrysler Buccaneer for $800.
We took out the Buccaneer on Lake Patterson near Dickinson, ND and had a pretty stressful first sail. At one point the side of the boat dipped under the water…very exciting. Hear me yelling "bail faster!" to Anna in this video we made of the event: https://www.youtube.com/watch?v=g9CH3XI5skc The Buccaneer went out three other times that summer, once me by my self, once Anna, Daniel, and myself, and one time I took my sister out. Small "dingy" sailboats are very unstable since they don't have weighted keels, and there is a definite risk of tipping it over and then struggling to right it again. So I can't say that I really enjoyed sailing that little boat. I didn't take it out this past summer and sold it to a guy who lives on Lake Patterson in July.
In February 2018 we went to Florida for sailing school. We went through Blue Water Sailing School in Fort Lauderdale for a week-long course that gives you the American Sailing Association 101, 103, and 104 certifications on completion. Those respectively are Basic Keelboat Sailing, Basic Coastal Cruising, and Bareboat Cruising. In theory with these certifications a rental company would let you take out one of their sailboats on a charter for a week or so without a captain (making it a "bareboat"). Also a boat insurance company typically requires experience or certifications like these.
The school sent us three textbooks to study ahead of time. Then when we arrived we spent most of our time learning the hands-on skills and then taking written and practical tests. We spent 6 nights on board the 43' Dufour Gib'Sea named Third Wish. We both learned a lot that week and passed all of the tests!
Our most recent sailing was in the early summer when we went to check out a Tashiba 36 on Lake Sakakawea. We spent an hour or so examining the internals of the vessel and then went out for a short cruise along the lake shore. Ultimately it was more expensive than what we want to spend and not a great interior layout, but it was a beautiful day to go out for a sail.