& How did we learn how to sail?
Let's back up a bit and talk about our sailing background (and lack thereof), while answering the question of how Jimmy and I took up sailing. The short answer is that we were looking for a hobby to take on as a couple. When we decided to try out sailing, we had no clue how impactful that hobby was going to be.
Early 2006 Jimmy suggested that we learn to sail as a hobby for us to do together. Apparently, he had lightly dreamed of sailing, although he had never been on a sailboat. In the late 80's I once dated a guy whose parents sailed a lot, and I had the opportunity to go out with them and their friends on two occasions. The first was a day sail on a one of their friend's boats that departed the dock on a sporty day after gorging on a massive Easter morning breakfast. I never lost my breakfast, but I sure was feeling quite queasy. Someone said that the large meal before a sail was probably the culprit. That summer his parents invited me to join the family on a multiday trip to Santa Cruz Island from the Ventura Yacht Club. This time it was a fabulous trip where we anchored out at a different cove each night, explored the area by dinghy after dropping anchor each day, swimming in the water and hiking where we could find spots to land the dinghy. That same summer I moved to Alabama and never got onto a sailboat again until Jimmy suggested we learn how to sail, seventeen years later.
Jimmy did some research and signed us for sailing lessons with a school over in Pensacola that offered courses certified with the American Sailing Association (ASA). It took a few weekends of classroom and time on a 22' Capri for us to complete the ASA 101 course and earn our Basic Keelboat Sailing Certifications.
Armed with courage we jumped in the figurative deep end and purchased a 25' Hunter in Shell Point, located about 40 minutes south of our home in Tallahassee. Hindsight has revealed that we should have started out with a smaller boat, but we were excited to put our new skills to use. As we handed the check over to the very happy boat seller, he explained that we will need to carefully watch the tides in order to get out of the marina. I do not recall if he ever explained the channels to us or not but we began to learn those channels well after getting stuck hard aground at least twice on the few times we took the boat out. When we did take the boat out, I never docked the boat, and I rarely took the helm. It was my job to run around and do magic tricks with the lines (rope) of the boat. Later I learned that Jimmy hated how stressful docking was. Between the finding good tides to take the boat out, lack of navigation lights and our other life commitments, it turns out that we only took the boat out about every six weeks that first year, then even less during the second year. It became apparent that we needed to sell the boat and say goodbye to sailing.
Fast forward seven years to 2014. We are now empty nesters, and the sailing bug has come back to bite us. Once again, we jumped in the deep end, but this time with a safety tether by moving to Shell Point, joining the yacht club, and by not buying a boat. We worked on our sailing skills by going out for day sails with other members, and eventually by crewing in
races. In 2016 we had the opportunity to participate in a Pro-Am race week in the British Virgin Islands. In addition, I started to dabble in dinghy racing where the first year or two I would finish last or near last, but sticking with it, I started to move up in the pack. Other people's boats are a great way to improve your sailing skills!
However, this could lead to the desire to buy another boat. Two years after moving to Shell Point, we purchased an even bigger boat, About Time, a 32' Sabre, and docked her behind our house. Some big changes for us with this boat was that we had the time to dedicate to take her out to further develop our skills, and I took on more roles on the boat, spending more time at the helm, learning the boat's systems and eventually docking the boat. We even started racing with the Sabre taking on crew regardless of their sailing ability. Over the years with that boat, we honed our skills and took several multiday trips in her.
Eventually Jimmy and I decided that we both want to cruise full time but felt that a larger boat would be preferred for the two of us, our cat and the occasional guest. In order to avoid owning two boats at once, we sold the Sabre to begin shopping for the cruising boat. During the break between owning About Time and Utopia in 2021, we signed up for the ASA 103/104 courses. We went back to the same school that we took the 101 course fifteen years earlier, now renamed to Pensacola Sailing Academy. This time we spent a full week on a 39' Beneteau learning more about coasting cruising and what is needed for bareboat charters. Once again, we receive another confidence booster.
All of this background has been very helpful for us now that we have Utopia, a Caliber 40 LRC. I think stepping up in boat sizes is the way to go for boat ownership. Getting onto other people’s boats, dinghy sailing, and taking classes all have aided us along in this journey. There will be a lot more still to learn, but that is part of the adventure.
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