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OP here. Hopefully some inspiration for dudes who want to learn how to sail. Had to come to terms with the fact that I couldnt actually learn to sail from just reading about it soon after I posted this thread. Tried launching out of a my local marina and ended up stuck on a barrier and had to flounder for a bit while a bunch of people watched. It was very embarrassing, but one old guy told me to come down there on Thursdays and volunteer to race. Did what he told me and for a month I raced under the same skipper. Taught me a lot of stuff. Because I stuck with it I just accomplished my goal of taking my boat from one marina to the next town over's pier last weekend. On the way back I sailed back into the same marina I couldnt even get out of a month a go wing and wing, jib over the portside and main over the starboard. As I slowly made my way to the pier and the nearby Navy base began to play colors in the distance I felt like a real salt and swelled with pride. Dont let failure deter you. This is a tough sport to get into, especially if you never did it growing up. Network a bit and see if you can get an in with your local sailing community. From what I've seen most racing leagues are always in need of a few spare deckhands.