if you don't know where to start, begin with some books from guys that have been around for a while. Vigor, Roth, Hiscock, Neale, Calder, etc will all be very informative and will likely have either a big bibliography at the back or frequent reference of other books based on subject within the text.
They will lead you in other directions based on need/interest and you should start to get comfortable with where you need to go once you spend some time on board.
Don't be afraid to join an organization like RYA, Sail Canada
or US Sail for the access to more infomation and other sailors for the same reason.
I'm not too familiar with US or Sail Canada
, but RYA has an extensive library of their own.
Canadian and US Power and Sail Squadrons are another good source of information.
If your after historic context that can still be useful, start with Slocum and expand from there.
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