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Old 10-11-2013
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Re: Very n00b questions from a prospective sailor.

Therm, you mention being close to NYC. I have one of my trailerable sailboats at Spruce Run Reservoir near Clinton, NJ. It only cost me $295 to keep the boat rigged on the trailer at the boat launch for the sailing season. I can be launched and out on the lake in about 15 or 20 minutes. I have bigger long term goals than my current 16' and 22' boats, but I am just learning how to sail myself. There are some very affordable trailerable sailboats around, and you don't necessarily need a truck to tow and launch them.
As far as lessons go, my wife and I did a 4 day liveaboard ASA 101/103 course on the Chesapeake Bay this summer. It was awesome! Even my wife(who was scared of sailboats) had a great time. It was $750/person for the class and books, we stayed on the boat, and it included breakfast & lunch. It was worth every penny! I probably learned as much in those 4 days than I managed to teach myself by mistake in my entire first season. However, I went into the class with a basic understanding of sailboats that definitely helped. There are some very affordable options out there if you keep looking around.
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