Agree with almost everything posted...
be very careful to use a sealant, NOT an adhesive. An adhesive will make doing this down the road (either for you or for the next owner) extremely difficult. Besides, most adhesives, even if they also proport to be great sealants, are not as pliable. And you want the sealant to be pliable. Toward that end, read through Don Casey's book, "Sailboat Hull and Deck Repair". Everything Rob put in his post is in Casey's book, and then some with drawings and fairly detailed How-To instructions.I do respectfully disagree with Ross' post, provided that I have read it correctly. Countersinking your deck will weaken the gel coat, and bring the edge of the hole closer to the edge of the hardware. It will ultimately leak. No problem with countersinking the deck hardware or teak handrails (most of it already is). My preference would be to use a bolt with a flat surface mated to the flat surface of the deck/boat. By example, using a bolt to secure a new piece of acrylic window. Instead of counter sinking the acrylic, I used a flat headed bolt with a finish washer; it was neater and I had more mating surface (joint between underside of bolt head and acrylic) for the sealant to bond. Most of this is covered in Casey's book.