Re: CAULKING
Can you post a picture?
Best thing to do is go to the manufacturers websites and read about their products. Then order from iboats. 3M and Boat Life are two very popular marine sealant manufacturers that make various sealants for various applications.
Do not under any circomstances use siicone. Even the blue stuff. Unless you want to be cleaning up the mess next season and doing the job over again.
Is the transom wood by any chance?