First, are the teak rails over a cored section of the deck.
If so, then I would drill each screw hole oversized and fill it with thickened epoxy and let it set. Then re-drill for the screws. That way, the thickened epoxy will protect the core and give the screws something a bit more substantial to bite into. However, it would be better would be through-bolting the rails than screw them.
In any case, I would drill a small countersink into each of the screw holes in the deck. This will allow the sealant to form an "o-ring" at each spot. As for the sealant, I would use 3M 101 or BoatLife Life Calk. They're both really good for use on oily woods like teak.
I hope this helps.
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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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