Best time of Year to Caulk

[Captin Ron]

Hello,
I have just purchased a sweet looking 32+ Chris Craft.
It is in need of some planks to be replaced, which I plan on doing soon!
Does anyone have an opinion on when to caulk my boat with cotton? She is dried up completely and I will swell it first. My main concern is this winter in the Northeast. Will it dry out completely again and the caulking will need to be replace. I'm a first timer with restoration and would like to time it right.

Thanks

[Dr. J]

Captin Ron, I have just stumbled upon this site,and I am curious as to the outcome of your situation. I am a shipwright living in Vancouver, B.C. Canada. I concentrate most of my time in the repair and maintainance of marine craft of carvel construction If you have not begun repairs to your boat , please feel free to e-mail me if you require advice. I assume that the website will automatically direct you to my contact information. Good luck with your project,
regards, Jay