Join Date: Feb 2010
Location: Narragansett Bay
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If you take more than just the basic keelboat course and move up to coastal cruising and bareboating, you should find yourself comfortable handling a boat up the mid 30 ft range. People's aptitudes differ, so you could be more or less.
There are many things you might not realize are not standard on sailboats, such as refrigeration. If you will live aboard, you will want electric refrigeration, some may have ice boxes.
Also, for livability, you will want freshwater holding and you will also want to check the quality of it on the boat you buy. Many will not take good care of the freshwater tanks, unless they ordinarily stay aboard for lengths of time. If neglected, your only real solution may be to replace the tank and hoses.
This can be stretch in smaller boats, but having a separate shower stall is very nice if you are spending any time aboard. Otherwise, the head typically doubles as the shower and you have to dry it in order to have a usable head again. No big deal, but I find (used to find) having to do so every day for a long time to be tough.
A holding tank for blackwater (sewage) is probably going to be required.
You don't mention whether you are sailing alone or have a crew. The fewer people you are going to have to sail her, the more important it is to have every line return to the cockpit.
Good luck and welcome aboard.......
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.