2021
Rob Windsor
By : Chris Szepessy
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…” ■
2020
Born to Sail
From transatlantic sails to surviving a shipwreck, Rob Windsor has made a career out of his love of sailing
Issue: June 2020 By: Paul Koenig Photography: Nicole Wolf
Rob Windsor has sailed across the Atlantic Ocean nearly a dozen times, usually with just one other person on board. A professional sailor based in Portland, Windsor specializes in racing Class 40 vessels, which are 40-foot-long boats designed to be sailed by one or two people. When he’s not sailing, he helps prepare other sailors and their vessels for trips, including some solo sailors circumnavigating the globe. However, his schedule this summer is uncertain, with many races being canceled because of the coronavirus pandemic, including his favorite: the Atlantic Cup. The race, held every two years, covers the more than 1,000 miles from Charleston, South Carolina, to New York City to Portland, where it concludes with in-shore racing around Casco Bay. “These boats are made to go in a straight line for a really long time,” Windsor says. “They’re not made to be zipping around Fort Gorges and doing a lot of twists and turns. It’s kind of like trying to take a NASCAR race car and doing a slalom course with it.”
Is it nerve-wracking being out in the middle of the ocean with just one other person?
Honestly, being in the middle of the ocean is a lot easier than sailing in Casco Bay. In Casco Bay you’ve got rocks and buoys and boats, and there are shallow spots. In the middle of the ocean, there really isn’t anything to run into. It’s much easier to look after yourself and the boat, because you’re going in a straight line for a couple thousand miles. I think a lot of people get nervous because you’re far away from help, which is totally true. But if you know what you’re doing and you take care of your boat and yourself, it’s really quite nice.
What do you have to do to prepare for a transatlantic trip?
A transatlantic trip takes between 10 and 15 days if you want to sail from Maine to England. But the preparation for that is months of making sure that everything on the boat is in good working order. Things get replaced and changed and fine-tuned. We have to prepare for how long we think it’s going to take so we bring enough food. Some of the boats have desalination, so we can make our own water from saltwater, but some don’t, so we need to figure out how much water we’re going to need to bring with us. And the weather is a big deal. We try to look at a really good window of weather, where we’re going to not sail into a hurricane or do anything not safe. That takes a long time to figure out.
“I was on a catamaran that cracked in half and sank 300 miles off North Carolina.”
Have you been in any bad weather in the middle of the ocean?
I was on a catamaran that cracked in half and sank 300 miles off North Carolina. We got picked up by the U.S. Coast Guard. I’m only alive today because of them. We had thought we had a really good window to go from Saint Thomas in the Virgin Islands to Annapolis, Maryland. And about eight days in, we got caught in a really nasty spring storm. The waves got really big, and the boat came apart. The port side of the boat cracked, and we had to set off the emergency locator beacon and get rescued by the Coast Guard.
That sounds terrifying.
You know, it’s funny. Everybody says that, and it wasn’t scary until I had to get off the boat. The boat didn’t just sink from underneath us. Boats take a long time to go down. And when I had to jump off the boat, which was broken and sinking into the water, and paddle over to the rescue swimmer coming down from the helicopter, that was the only time it was really scary. The rest of it was kind of in survival mode and trying to make sure that we were all safe.
How big were the waves?
The Coast Guard said that the waves were 40 feet. On a regular day at Higgins Beach, let’s say, the waves are 3 or 4 feet. And if you wade out a little bit and you stand there and let one hit you, it’ll knock you over. And so, multiply that by more than ten times. That’s how big they were. They were huge. Impressively big.
Do close calls like that ever discourage you from continuing to sail?
Never. We got back to the United States on a Wednesday, and I was out racing on Saturday. I think when bad things happen the best thing to do is to get right back out there. To be honest with you, it wasn’t super terrifying. I know it sounds ridiculous, but it wasn’t. I was upset that bad things happened, but at the same time sailing is my favorite thing to do in the whole world, and somebody pays me to do it.
2017
Sailing the high seas with wounded veterans and a few modifications
Warrior Sailing Program gets veterans into the water, learning new skills on some of the world's fastest sail boats.
Author: Amanda Hill (NEWS CENTER Maine)
Updated: 7:10 PM EDT October 10, 2017
(NEWS CENTER) -- "The U.S. military does a really good job of making sure these guys are very regimented and listen, and if you tell them what to do, they'll do it." Rob Windsor is one of the instructors of the Warrior Sailing Program.
It was founded just a few years ago by Ben Poucher, who wanted to give back to those who've sacrificed a lot for their country.
The program gets veterans who have wounds, physical or otherwise, out onto the open water.
"I am impressed," said Windsor. "I have some friends and I have made some friends from being involved in the Warrior Sailing Program that are competitive sailors and that sail just as well, as long as we have some adaptations to make it to get them around the boat. Normally I move from one side to the other, and if I have you strapped in a chair that can't happen, so we have to figure out how to make it a little easier to get around the race course for some of the disabilities people have, and we have done that. We have made adaptations to the fields we use so we can make it so that everyone is safe and can still do their job to finish the race."
Windsor helps instruct new sailors off the coast of San Diego, but hopes to bring the program to Maine, where he spent a lot of his time growing up.
"You watch a guy come down the dock with the biggest puss on his face and we pull a couple of strings and I say, 'Hey we're sailing,' and that smile makes it all worthwhile."
To learn more about the program, or how to help, click here.
2016
Sailing World Magazine October 2016