Am I a sailor yet?
The first time I sailed was about 12 years ago while I was living in Pittsburgh. A friend casually mentioned that a woman in his office was planning a sailing trip on the Chesapeake. I always wanted to learn how to sail, so I suggested that he ask her if we could go. Having planned vacations, I was familiar with the difficulty of getting people to commit with money. As I suspected, there was space available for us!
The sailing trip began at a marina on Solomon’s Island in Maryland. We made the five hour drive after work. The crew was to meet at the Tiki Bar the night before our sail. We only knew Sue the organizer, so we looked forward to meeting our new friends and our Captain.
I’ll never forget meeting Captain Dave. As luck would have it, he turned out to be the salty dog character at the Tiki Bar, with a gruff beard and dark tussled hair, that had one too many MaiTai’s. I of course avoided eye contact and ignored whatever words he slurred when he sat in the chair next to me that my friend temporarily vacated for a trip to the restroom. We had no idea he was our Captain at the time because we had not yet met any of the crew. You can imagine our surprise when we were introduced. Ultimately, Dave was harmless, but he was definitely a character with many stories. I heard he has since retired from his civilian Navy job (Physicist iirc), sold his boat and is doing well playing poker tournaments in Vegas.
Captain Dave was used to racing and winning on Krugerrand (a Morgan 36), so my introduction to sailing involved him yelling a bunch of commands that I did not understand. I barely knew the difference between Port and Starboard. He didn’t yell out of anger or frustration, it’s just what was he was used to from his competitive racing days. Nothing personal. Just urgency. I learned a few new things about sailing and the boat on each trip, but I admit we weren’t a hard working crew. To this day, I still enjoy sitting at the bow or under the main if I not at the helm. 
Over the years, I sailed the Chesapeake a few times each summer with the same group of people that I met on that initial sailing trip. I also made two trips to the Caribbean. During the first trip, we sailed around the BVI on a Beneteau 50 which is a common charter boat. On the second next trip, we sailed around the lessor Antilles including St Bart’s and Saint Martin on a catamaran. By the way, it’s worth noting that I had the best dinner ever at the Fish Pot. Well, up to that point in my life anyway.
I thoroughly enjoyed both sailing trips, and I could write detailed blogs about each. Ah, ok. Just a few short notes. Snorkeling is better in the BVI. I suspect this is because there are more moorings and the coral reefs are protected from anchors, but what do I know. Painkillers at the Soggy Dollar on Jost Van Dyke. The Baths. The Caves. Willie T’s. Enough said. St. Bart’s is exactly what you expect it to be except even more colorful.
I moved to Boston in 2002, and I’ve since spent many summer weekends on a boat in Newport, the sailing capital of the world and former home of America’s Cup. You want to sail? This town is drenched with experienced sailors, beautiful boats, and captivating views. It’s a small town, yet it is surprisingly international.
Fortunately, many of my friends are experienced sailors, and I have learned quite a bit from them over the years. They are very patient teachers. I’ve learned about navigation, maintenance, tide charts, safety, troubleshooting, and of course knots. I am grateful for all they have shared with me over the years. Last summer, I started racing on my friend’s 1926 Herreshoff S Class boat. On a classic yacht with a wooden mast, you don’t want to screw up. I was essentially ballast for the first race or two, but now I’m considered to be experienced crew. Progress! 🙂
I’ve learned quite a bit since my first sailing trip, yet when asked if I am a sailor, I always hesitate to answer. Compared to most of my friends and the sailors I meet? No. Learning about sailing is endless, but in my heart I know the answer is yes. Most sailors would tell you there is always something new to learn.
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