I start off cold, but I'm warm 5 mins. and one hill later. Last year, I mostly wore silk long johns under my pants, a longsleeved silk undershirt, a polypro or wool t-shirt and a ski jacket w/ pit zips. I always wear a skull cap, even in summer, to keep from getting helmet hair. When it got really cold, I put on thicker long johns, wore the zip-in fleece that came w/ the ski jacket (also has pit zips) and a balaclava. Eddie Bauer gloves that I got on sale and good wool socks to complete the outfit. As for being near water, I live on the tropical isle of Manhattan.
This year I picked up some more wool shirts to wear when it gets wintry. Wool wicks, dries fast and doesn't smell as funky as polyester. Plus it's stylin'.