Question: Four of us sailed my 36-ft Moody Halberdier from Buffalo, New York to Rimouski, Quebec in Oct./Nov. last year. The biggest problem was cold feet. Sailing boots with extra socks did not do the trick in -5°C weather. Rubber boots with liners were OK. I’m planning a trip to Northern Labrador next summer. Any advice on footwear?
Answer: Keeping feet (and hands) warm and dry is definitely the toughest clothing challenge when sailing in cold weather. We used to use Guy Cotten Astron rubber boots, which have an air 
cushion sole that provides insulation from a cold deck and removable liners (see http://www.guycottenusa.com/ and follow the link to “Fishing”). We’d have several pairs of liners that we would rotate through as they got wet and buy the boots big enough to fit several pairs of thick socks. As you said about your rubber boots, they were OK.
Then we met a sailor in Svalbard who had leather boots with Gore-Tex linings. Wow! (Our reaction both to the boots and to the price!) After one too many cruises with cold feet, we finally broke down and bought two pairs of DuBarry Ultima boots. So far we’re thrilled with them, but we haven’t used them for long enough to give them an unconditional thumbs up—we have to see about their longevity.
Boots aren’t the whole story, though, socks matter too. We used to use synthetic socks until we discovered the joys of SmartWool. Trust us, wool really is smart—it wicks moisture away from your skin, keeping your feet warmer longer. We have several pairs, of different weights, that we rotate through as they get wet.
And, when none of the above is managing to stave off the cold, dancing in the cockpit is another strategy I have used on occasion!
