Our Sailing Story

    We took something of a round-about path to the sailing lifestyle. I remember very well the first time I had the idea that this would be the kind of life I'd be interested in. It was Wednesday May 28, 2008 and I was playing online poker one evening, as was my standard habit back then.  The game was very easy to beat and I was reading an online poker forum while I played.  Someone had written a post there entitled "ask me anything about sailing around the world" where he spent the past week telling many tales about life at sea in a 41' monohull.  At the time, I had no idea this was a thing that people did.  I eagerly devoured everything he said, all the stories, all the tales of drama and adventure and thought this seemed like an absolutely incredible life.  I asked him to estimate how much it cost to live a life like that (a question I have since fielded a number of times myself).  Of course, he responded that one could do it for next to nothing or spend a fortune.  It all depended on what you wanted to do.  So far, we are trending more towards the spend a fortune end of the spectrum.

    I had another friend on that forum who started working as a crew member on sailboats and sailed around the world.  He was kind enough to meet up with me at the World Series of Poker one year and answer all my questions.  By then, I had discovered that there were some people on YouTube documenting their adventures in the same life.  We watched a lot of these YouTube videos together but I think it was Gone With the Wynns that eventually convinced us that this was definitely an attainable vision.  The Wynns didn't spend an exorbitant amount of money and they didn't seem to possess any skills that we didn't have (other than being beautiful and able to shoot awesome videos).  They bought a boat with more or less no experience at all and took a few classes and ended up sailing in the South Pacific and as of the time I write this, they haven't died.  We decided if they could do it, so could we. They seem mostly quite happy.  We've made some small financial contributions to their channel and have met them and talked about how one would do this thing.

    Lisa and I aren't the buy a boat with no experience and figure it out kind of people.  We are children of librarians, so we filled our house with books on sailing, watched all the videos, joined all the websites.  We started the process of getting an education by taking sailing classes and going to boat shows.  We worked our way through the ASA sailing classes and took every boat show seminar you can take.  In 2018, we had enough classes to qualify to charter our own boat, so we flew to Grenada and spent a week on a Leopard 40 with some close friends.  Our first big sail was across to Carriacou in pretty sporty conditions against a head wind.  This is not the kind of thing that a sensible person on their first charter.  It is the kind of thing we do, however.  That poor little Leopard was absolutely not cut out for any kind upwind component.  Lots of stuff broke, we looked like we might get stranded without any chartplotter and have to do everything manually, but we still had an absolute blast.  A year later we did a charter in Antigua on a 45' Lagoon (the same boat that is having all the bulkhead problems right now) which followed a similar pattern -- lots of stuff broke but we still had a blast.  

   We were now getting pretty serious about wanting to buy our own boat, so we wanted to figure out what the worst part of the life was.  We decided a long ocean crossing would probably be about as unpleasant as it got, so we found someone who needed help getting across the Atlantic and we offered to join as crew for the voyage, taking shifts at the helm and figuring out how it all worked.  It was a long and crooked path, but we made it across in the summer of 2019 to Portugal intact, with stops in Aruba, St Martin, Bermuda and the Azores along the way.  Some of it was difficult, but we were undeterred.  By this time, we were shopping in earnest.

  Our shopping reached a fever pitch in 2020, when we were really fed up with the state of the world with COVID and everything else.  Unfortunately, every other dreamer in the world had the same idea.  We had I think 3 different boats fall through over the course of 2020 for one reason or another.  In 2021, we got a good lead on a Privilege 495.  Prior to that, we were quite sure we were going to buy a boat that was only a few years old, manufactured by one of the big names like Leopard.  Once in a while, we thought we might end up with a Knysna which is a beautiful boat, but they make so few of them that finding one was nearly impossible and Lisa was holding out when I proposed buying a new one, because one of us has to have some sense and it certainly isn't going to be me.  We ran across a Privilege 495 that was older than what we had been looking at, which is good because they are very expensive boats and a new one would have required me to sell internal organs.  It looked pretty good and we made an offer that was accepted.  Now it was time to schedule a survey and make our final decision.  In a mad panic, we reached out to a bunch of people for opinions on the boat.  

    One of the people we reached out to was Jamie & Behan Gifford of www.sailingtotem.com fame.  In a weird coincidence, they knew someone who was selling the same model of boat.  Except the one they knew about was a year newer, slightly cheaper and looked to me much better equipped.  In his characteristic no-nonsense style, Jamie more or less said we'd be foolish to buy the boat we were looing at when this other boat was an option. It was a for sale by owner transaction, so there were no brokers to hold our hands and we did all the negotiating with the previous owners by email because they (and the boat) were in Panama.  We were incredibly fortunate that these folks turned out to be very nice and helpful and generous with their time and we eventually fell in love with the boat.  Our surveyor didn't find anything too serious and we were able to finalize the deal without anyone getting angry.  Probably they found us a bit annoying, but they've done a good job of hiding it and we still chat from time to time.  On May 27, 2021 we officially became the new owners of Dragonfly!

    We needed to get some work done so that our insurance company wouldn't be too obnoxious, which dragged on and on and in the end they didn't get everything done we wanted anyhow.  But we got the boat back on October 21.  We started making mad preparation for a winter in the Bahamas and headed south on November 28.  Hopefully, the rest of our story on Dragonfly will be here on the blog.