Join Date: Mar 2010
Location: San Francisco bay
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Re: My dream has always been to live on a sailboat. Tips please
I would begin with a membership to a sail club. Or if you can't find one, get a cheap dinghy. You can find some that are cheaper than the price of the resin you would need for a 30 foot fixer-upper.
Sailing a dinghy is more useful to learn wind and sails. Dinghies are also more forgiving and easy to repair if you misuse them.
Sailing on a dinghy is much more pleasant and will give you more satisfaction. You can use them to backpack around if your lake is large enough and can easily pull them on the beach. They are usually responsive and fun. The only thing that is important is that you know how to right yours if (when) it capsizes.
When you're ready and you know you enjoy sailing, sell it or give it away. Or maybe keep it and sail it while you work on your bigger boat.