Join Date: Mar 2006
Location: New England
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A good book to start with would be John Vigor's 20 Small Sailboats to Take You Anywhere.
Yes, you can buy a bluewater capable boat for the budget you've got in mind, but it might have compromises you wouldn't need to make on a larger budget. All boats are compromises and finding one that has the compromises you can live with is the key.
I'd point out that if you're looking to just cruise the Caribbean, you may not need a full bluewater cruiser, as many people have cruised the Caribbean in coastal cruising designs, by picking their weather windows rather carefully.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.