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I noticed that all of the teak pieces that I removed to refinish ( i.e. cooler cleats, bimini anchors, etc) were caulked in each screw hole. Not sure if whaler did this originally or was the idea of the last owner?

Is this something that others recommend to keep water out and if so does any one have a specific product they recommend?

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It is highly recommended you dab some marine sealant on the shank of the screw just below the head.

Any marine sealant will do. One of the many brands is Boat Life. I do not recommend 3m 4200 or 5200 since they are a combination adhesive and sealants and overkill.

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Varnish works well also. I just dip the screw in a small container of varnish and run the screw in. Just wipe away any excess. It does a good job and releases easily when the screw has to come out. Also solves the problem of the white ring around the screw head.

Another approach is to drill out the hole to about 3/8 inch and twice as deep as the screw. Fill the hole with epoxy and let it set up, until it's not quite hard. Drill a pilot hole and run the screw in. This forms a water tight threaded hole which can be used again and again and is stronger than a screw just run into fiberglass.

The really Bristol method of dealing with screws through or into teak or other wood, of course, is to use plugs of the same wood to cover the screw head. In that case ALWAYS use varnish to seal the plug. the grain in the plug should run the same direction as the grain in the larger piece. Done properly the plugs almost disappear.

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although marine sealant is recommended it gets a bit expensive. When you just have a screw or two to do. I have used tub and tile caulking made for use around water and it seems to work okay for me. It's a little less expensive than the marine caulking and seems to do the job.