©Billy Black/billyblack.com

Pro sailor, race boat preparateur and one of America’s finest doublehanded racers, Rob Windsor has competed in every edition of The Atlantic Cup.

“I was born in Maine but grew up in Centerport, New York,” says Rob, who resides in Portland, Maine. “I’m adopted and my parents had a Columbia 22 when they got me, so I’ve been sailing since before I can remember. Their next boat was a Pearson 26, and I remember cruising Long Island Sound and New England until my teens…four of us including my sister on a 26-footer for the summer. When I see those boats now, I can’t believe we did that for weeks at a time on something so small! I started racing Blue Jays when I was 8 and that had me hooked on sailboat racing ever since.”

Notable sailing sages have guided Rob’s path. “Rich du Moulin was the big guy on Long Island Sound when I got started in shorthanded sailing, and he still is,” says Rob. “I still check the results when we’re racing in the same event to see if we beat him on time even if we’re in different classes. Competing against Rich made me look at sailing to my strengths, and working the weather and numbers to get the best results. Rich Wilson has likewise always been on my radar. He’s an amazing guy: two Vendée Globes, numerous world records, and the fastest American non-stop around the planet! I learned a lot from watching Rich, but the biggest thing is perseverance. He’s not the biggest or the strongest guy, but he makes it to the finish line. Brian Harris was doing what I wanted to do before it was even really a job here in the U.S. He’s been on the shore team for multiple Vendée and Around Alone races and some world record attempts including for Rich Wilson. From him I learned the value of preparation: you think about how the race is going to go and what might be a problem and then figure out a solution before it even happens. Hope for the best but plan for the worst. I’ve learned a lot from him, but that’s the best.”

“Having raced on fully crewed boats for a while, I found myself bored with only doing one job,” says Rob. “I had done some doublehanded sailing on a few boats and really enjoyed it. I was working for Mark Washeim at Doyle Sailmakers (Mark is now OneSails NA) and he had a customer, Michael Hennessy, who owns the Class40 Dragon. Mark asked me to sail DH with Mike in the Greenport Ocean Race. We came second across the line to a fully crewed Swan 42, and that was it for me! The easy speed and power was close to what I’d seen on some fully crewed boats, but without all the people. I really am a people person, but having all the controls and being on deck alone doing 20 knots in the middle of the night is pretty great! Knowing there’s someone else to share the duties makes it easier to push the boat and yourself.”

“I’ve done eleven transatlantic crossings – seven of them doublehanded – and one transpacific,” says Rob, who has logged more than 300,000 sea miles. In 2013, he and Hannah Jenner sailed 11th Hour Racing in the 5,450-mile Transat Jacques Vabre. “The TJV is an incredible event, and it’s a very different kind of race in that it’s so long. Hannah and I made a good team. She’s as tough as nails, and sailing with her was awesome. Sailing with Hannah and other women I’ve had the pleasure to race shorthanded with has made me a better sailor. Women use their heads more than men…at least more than I do. I always figure if I pull harder, eventually it will come. I learned from Hannah and the others to take a moment to think before doing.”

“Being an 11th Hour Ambassador and sailing under their banner was really great. They do a lot for the sport and the environment. Keeping the oceans clean for future generations is a responsibility we all have, but it starts on the water with sailors. Setting an example for others in the sport to follow is a big part of it.”

Rob’s business is called Rob Windsor Sailing (robwindsorsailing.com). “Most of the time, I get racing boats ready to race and sometimes I race on them,” he explains. “I really enjoy the preparation part of the game. I do some Class40 measurement work. I’m not a certified measurer, but I’ve been the boat captain on six or seven so I know what’s needed and how to accomplish it. Class40 is a great platform. The boats now have gotten to the very end of the box rule. They are way faster today than any of us thought they could be.”

“I’m doing the prep on the Class40 Gryphon Solo 2 for Joe Harris, who is doing the Globe 40 in 2022. I think there may be some work for me if any of the U.S. guys want to do The Race Around. Basically, I do whatever is needed so I can stay in the sailing business and go sailing.”

“The Atlantic Cup is my favorite event in America,” Rob enthuses. “It’s the best because it’s so hard to win. The offshore legs are tough, but the inshore racing component is the hardest. The boats are set up to race shorthanded, so having six onboard gets a bit crowded. I’ve done every Atlantic Cup – six now – on three different boats with three different co-skippers: three with Mike Hennessy on Dragon, two with Micah Davis on Amhas, and one with Emma Creighton on Initiatives. Made it to the podium a few times but haven’t won one yet…” ■