I still remember our first sail trip up to Port Townsend. It was during the kids’ spring break in 2015. We set out in our first boat, the Aequus Aer, at about 5 a.m. in the morning to ride the tide 35 nautical miles north. 

I was at the helm with a warm hat and gloves on, a blanket wrapped around me and both my kids snuggled up nearby. By the time we got to PT, I was shivering and couldn’t fully warm up until I got into the marina showers that night.

I am one of those people who runs cold all the time. Plus, I have Raynaud’s syndrome. You might think I’d be inclined to take a break from cruising the Pacific Northwest between the months of October and April, but instead I’ve become all the more determined to make sailing a year-round activity for my family and me. 

Our desire to sail in cooler weather is a big reason why we purchased the boat that we did. But even if we hadn’t, I’ve found that by planning ahead, investing in good quality gear and having a back-up plan, it’s been possible for me to spend most of the time “top side,” even during the rainy, cool Puget Sound winters. 

Tip 1: It’s easier to stay warm than to get warm

As important as Newton’s Laws of Motion (to me, anyway) is the fact that it is much more efficient to get warm before we start sailing than to get cold and try to warm up while we are underway. 

To that end, I eat hot meals, drink hot tea or decaf coffee, and start bundling up while I’m inside our warm, heated boat. I cool off very fast and, because of my Raynaud’s, the first place I get cold is in my feet and hands. So after warming up my insides with food and drink, I put on a warm hat, warm leggings or thermal underwear and either a heavy wool sweater or down-filled jacket. WHILE I’M STILL INSIDE THE BOAT.

And I always don my big, ugly overpriced Uggs while inside to insulate my feet from the cold boat floor. 

Yes, I do start to sweat with all this on, and yet, my hands and feet at this point merely feel tepid. That’s when I know I’m off to a good start. 

Tip 2: Buy the best, warmest, most waterproof gear you can

Foul-weather jackets, sailing bibs, thermal underwear and good wool socks can cost a small fortune. I have acquired them as Christmas and birthday presents and congratulatory splurges I’ve made for myself. I have never regretted spending a single cent. (Shop REI Outlet, Sierra Trading Post and West Marine’s off-season sales for the best deals.)

After sailing for three seasons in a pair of inexpensive rain boots, I asked for warm, non-marking snow boots from Columbia for Christmas. Santa delivered and I’ve been a much happier sailor since. 

In addition to my new boots, here’s my typical get-up for a really chilly winter sailing day. I’m sharing the brands, models I wear in case you are in the market for new gear, and I would love, LOVE to hear what works for you. Here goes: 

• First layer: Fleece-lined jogging tights and a mid-weight thermal top. (I like tops from SmartWool and from Kari Traa because they fit me the best and are fitted enough around the neck to prevent any breezes from going down the front. Cold boobs are no bueno.) I am starting to experiment with heated socks on really cold days. I just bought these on Amazon. They are battery operated and have three heat settings and so far, I LOVE them. On warmer days I don either well-fitting wool socks (I’ve tried SmartWool and some lesser-known brands, and all seem to work well)
• Second layer: Waterproof sailing bibs, a fleece neck gaiter and a fleece vest I got from REI 10+ years ago. 
• Third layer: Either a heavy Norweigan wool sweater (those Scandinavians know what they are doing) or a down jacket. The one I use is filled with down-alternative from Marmot. I got it on sale from Sierra Trading Post.
• Fourth layer: A foul-weather jacket from Gill and a fleece-lined wool hat. I have several hats I’ve purchased from REI and from Sierra Trading Post. 

I saved gloves for last. Nothing keeps my hands warmer than a good pair of waterproof snow mittens. The only problem is I can’t trim sails or handle line very well with them on. So, I decided to buy a pair of Hestra mittens about two sizes too big for me. I wear my favorite sail gloves and then stuff my hands into the mittens, with the gloves still on. If I need to perform some task that requires dexterity, I take the mittens off for a second and do what needs to be done.  

Tip 3: Have a back-up plan

I hate single-use items. It creates trash, which isn’t good for the environment and also a pain in the butt when you are cruising and don’t have access to a place to dump your trash when you go to shore. (This is the case at many state parks in Washington.)

That said, those instant hand and feet warmers, the kind you open and shake to activate the little iron pellets inside, have saved me from losing a finger or toe to cold-triggered numbness more than a few times. 

And if all else fails, I head down below and steer from inside our pilothouse. That’s not an option unless you have a boat with this design, but if you are in the market for a cruising boat, and plan to do some high-latitude sailing, I can’t recommend a pilothouse sailboat enough!

If you have any cold-weather sailing strategies to share, please do!