I’ve been asking myself this lately: As we emerge from our collective pandemic fog (hopefully sooner rather than later), will we go back to the good old days of regatta sailing? Or will some of us each go off in a new direction, following a path forced upon us by the isolation and caution that came with COVID-19? In my last column (“Rebuilding a Team,” Winter 2022), I suggested that now may be a good time to think about our own sailing teams—they’re makeup and how we can rebuild them to meet new goals. But the second part of this is about defining new goals. For myself, I used this winter to think deeply about my sailing projects and my aspirations. My recent seasons as a professional sailor have been immensely satisfying, competing alongside committed owners and their crews, and doing cool events in amazing places. But over time, I also felt something was missing: I need to do something truly epic. I’ve been doing the checklist regattas, but what about the ol’ bucket list? Wouldn’t now be a good time to fill it? If not now, then when?
I suspect many of us have our favorite sailing events already lined up for this year, which is great. But what about adding in something different, something totally crazy and new? I also suspect we all have fantasies of racing in new events, sailing cool boats and going to exotic locales. Maybe now is the time to do more than dream about it. So, I challenge you to sit and wonder what you’ve always wanted to do with your sailing. Make a list of your secret fantasy events. Racing in the Caribbean is a must. Going to a world championship—in any class—is super cool. Sailing on a new foiling boat? Completing a long ocean passage? Taking up wing foiling? Oh, the options available to us sailors—there are so many.
I’m sure we all have these kinds of aspirations percolating in our minds, but it’s so easy to keep doing what’s familiar, sailing in the same class or on the same boat for a long time, telling ourselves that’s how we get better, how we get to the top. Yes, it’s more difficult to try something new, but the rewards of exploring what else is possible can help us improve in ways we never expected. We may have to make compromises to break away and put these desires in motion, like finding a new sailing partner, getting into better shape, sailing a smaller boat, or cutting back on something else.
I am. For 2022, I’ve chosen to reduce my pro sailing commitments to make more time for races on my own. Specifically, I have always wanted to do all of the classic ocean races. While I have done many of the big ones, including the Fastnet, Transpac, Around Britain and Ireland, and the Bermuda Race, this year I am entering the Rolex Middle Sea Race and the Race to Alaska on my own boats (both of them shorthanded). For the Middle Sea Race, I will campaign a 33-footer, not the larger, faster yachts I usually sail. The 650-mile course can be quite challenging, especially doublehanded, with periods of very strong wind and no wind. But I’m told the scenery is fantastic, including the volcanoes of Etna and Stromboli, and the competition is always top-shelf. The challenge of preparing a boat from thousands of miles away and somehow delivering it to Malta will be substantial.
And for the adventuresome Race to Alaska, I’ve entered my Riptide 44. The unique rules of this race will require me to remove the engine and figure out a means of human propulsion. The innovative course from Victoria, Canada, to Ketchikan, Alaska, can be completed either east or west of Vancouver Island. My plan is to take the westerly route, which will put Dark Star in the open North Pacific Ocean for more than 500 miles. This, by the way, is one of the roughest patches of ocean around. Why would I willingly do this? Because it is a crazy challenge that I find fascinating. And nobody has ever completed this route on a racing boat before. In 2023, I plan to do at least two more epic events, which means I will be paying the bills rather than getting paid, but it also means I can create the program I want. Bucket list, indeed!
If the last two years has taught me anything, it is a recognition of how much sailing enriches my life, and how grateful I am to have the chance to race as often as I do and be with our sailing friends. I’m excited to take myself beyond my comfort zone, embrace these new sailing adventures, and do something amazing. None of us knows the future, so I say let’s get on with the now.